In this episode, Ashley and I talk about what this offering actually looks like, why we created it, and when it makes sense for advisors to bring in outside support.

Where This Idea Came From

Over the past few years, working closely with firms, one thing has come up again and again: advisors see real benefit when their clients have someone to talk to one-on-one — outside of the advisory relationship — about the stuff that doesn’t fit neatly into a financial plan. Life transitions, anxiety around money, couples dynamics, spending patterns, career changes, identity shifts. The list is long.

So we built a service around that need. A warm handoff — a place advisors can confidently send their clients, knowing they’ll be met by someone steeped in financial psychology and behavioral coaching.

What We Offer Referred Clients

• One-on-one sessions with a financial behavioral coach (45–60 minutes, for individuals or couples)

• Financial couples coaching — support around communication, spending dynamics, and shared decision-making

• Co-facilitated meetings — we join the advisor in difficult client conversations (multigenerational family meetings, tough spending conversations, high-emotion situations)

What We Offer the Advisory Team

This isn’t just a referral and a hope for the best. We’ve built tools and resources to help firms actually use the partnership well:

• Referral scripts and language guides — how to bring up sensitive topics and introduce a specialist naturally

• Signs-to-refer reference guide — what to look for, when to suggest coaching

• Training — so your team feels confident making the handoff

• Monthly email insights — case examples, tools, and reminders to keep this top of mind across your firm

• Client-facing materials — including a questionnaire clients can use to self-select into the service (great for client appreciation events)

When to Refer

Some of the common scenarios where this partnership fits:

• Life transitions & major decisions — retirement, business sale, sudden wealth, inheritance, divorce, widowhood, career changes, sabbaticals

• Relational & family dynamics — couples with money conflict, aging parents, adult children and finances, cultural obligations around family support

• Behavioral patterns & emotional blocks — analysis paralysis, chronic avoidance, values gaps, shame or secrecy around money, financial anxiety

• General curiosity — some clients simply want to explore their relationship with money, understand what they learned growing up, or get clearer on what they really want

How the Process Works

1. An advisor identifies a client (or a client self-selects)

2. The advisor makes a warm introduction using the referral tools we provide

3. We schedule a session — typically within a couple of weeks

4. After the session, we share relevant updates back with the advisory team (with appropriate client consent)

5. The client returns to the planning process with new language, new clarity, and often a deeper level of engagement

One thing that makes this different from a typical referral: you’re not left in the dark. We close the loop. You’ll know what happened, what came up, and what might be useful as you continue working with your client.

Why Us

We know financial planning — not because we want to do your job, but because understanding your work makes us better at ours. Ashley is a licensed therapist and financial behavioral specialist. I teach, write about, and research financial psychology. We both have deep roots in this profession, and our team does too. That means when a client says something that matters for the plan, we catch it — and we bring it back to you.

Get in Touch

If this sounds like something your firm could use, we’d love to talk.

• Website: beyondthefp.com

• Email: hello@beyondthefp.com

• LinkedIn: Find us both there — we’re always around

Here’s to going beyond.

Welcome to this month’s (Less) Lonely Meetings drop—a toolkit for turning each Less Lonely Money article into real, relationship-centered conversations.

Inside, you’ll find two ready-to-use tools:

• Client Companion — A reflection-first newsletter you can send to clients and prospects, exploring why curiosity and connection matter as much as any line item in a financial plan.

• Meeting Ready Guide — A practical outline for bringing conversations about community and belonging into your next 30-minute meeting—without scripts or therapy talk.

This month’s topic might surprise you: it started with small talk. The latest (Less) Lonely Money article explored the research on casual conversation—why most of us think we’re terrible at it, why it’s actually good for us, and why even the smallest exchange can be the start of something meaningful.

But for your clients, the takeaway isn’t really about small talk. It’s about something bigger: the role that curiosity, community, and genuine connection play in a life well lived—and well planned.

Many clients have done the hard work of building financial security. But security without belonging can feel hollow. Research consistently shows that social connection is one of the strongest predictors of wellbeing, longevity, and life satisfaction. And yet, it rarely shows up in a financial plan.

These conversations give you an opening to explore where your clients feel most connected, where they feel least, and how their time, energy, and resources might better support the relationships and communities that matter to them.

Let’s jump in.

Client Companion - This Month’s Client-Facing Newsletter

Newsletter Title:

The Smallest Investment with the Biggest Return

Best Used:

• With clients approaching or in retirement who may be losing workplace social connections

• During life transitions (relocation, empty nest, career change, loss of a spouse or partner)

• With clients who are financially secure but express restlessness, boredom, or a sense that “something is missing”

• When discussing time allocation, charitable giving, or lifestyle planning

Suggested Subject Lines:

• The Investment No One Talks About

• Why Connection Belongs in Your Financial Plan

• A Small Conversation Can Change Everything

Optional Intro Advisors Can Use: This month’s reflection is about something we don’t usually discuss in financial planning—but maybe should. It’s about the people, communities, and connections that give our plans their meaning. I hope it sparks a thought or two worth sharing.

Full Text (Copy/Paste into Email)

The Smallest Investment with the Biggest Return

Here’s something that rarely appears on a balance sheet: the quality of your relationships.

Not your professional network. Not your LinkedIn connections. The real ones—the people who know how you take your coffee, who you’d call at 2 a.m., who make an ordinary Tuesday feel a little less ordinary.

Research consistently tells us that social connection is one of the most powerful predictors of health, happiness, and even how long we live. It rivals exercise, nutrition, and sleep. And yet, when we plan for the future, we almost always focus on the numbers and rarely on the people.

That’s understandable. Numbers are concrete. Relationships are messy. But if a good financial plan is supposed to support a good life, then the relationships that fill that life are probably worth thinking about, too.

Why Connection Gets Harder (Even When Life Gets Easier)

There’s an irony worth noticing: the moments when we gain the most freedom are often the moments when connection slips away.

Read more

Unfortunately, though, this is not what the research says… which is both annoying and inconvenient for my personal narrative.

In fact, research often shows that small talk is valuable in both professional and personal settings—and, to my dismay, it even makes many people feel pretty good most of the time.

Side note: If you’re thinking, “I swear I read somewhere that small talk doesn’t make you happy,” you’re not wrong; I read that article, too. It made me feel totally vindicated and seen… but then I read the follow-up showing that the findings couldn’t be replicated, ultimately supporting the larger body of research suggesting small talk is beneficial.

Okay. Fine.

However, this research isn’t completely cut and dried, which is why this piece still felt worth writing. There were also a few other considerations that emerged as I read through the research—points that feel important for all of us to consider, whether we love small talk, hate it, or fall somewhere in between. I’ll go into more detail on each, but here’s the small talk version.

1. Small talk is poorly defined in the research, which creates challenges when interpreting the results.

2. Most of us think we’re bad at it (or at communication more generally), and that belief doesn’t help.

3. Small talk cannot (thankfully) go on forever if a relationship is going to grow.

4. It turns out to be good for us… who knew?

5. And yes, I clearly have my own issues with small talk.

To wit, if you are new to (Less) Lonely Money, this piece is going to feel a bit different from most of the other articles here. It’s shorter, more sarcastic (being unmercifully teased throughout my life about my disdain for small talk means my sarcastic voice is the only one I hear as I type), and probably best described as a passion project. Rather than a cry for closure or an attempt to find organizational footing around a complex, emotionally heavy topic, this time I simply wanted to understand why I just can’t stand small talk.

Not a Conversation Full of Tiny Words (But Not Quite What We Think, Either)

One of the first challenges in writing this article was figuring out which keywords to use to locate the research on small talk. Depending on the field, it shows up under a range of different labels, including small talk, rapport, off-task talk, first impressions, phatic communication, and interpersonal communication. I’m sure there are more.

As I reviewed the research, two distinct definitions of small talk consistently emerged—and they are not the same thing.

1. Brief, informal chats between strangers in random places. For example, researchers might examine what happens when total strangers talk to one another on a bus, often starting with small talk about the weather or another communally relevant topic, like sports.

2. Off-topic conversations in professional spaces between professionals and customers or clients. In this case, researchers could examine whether brief, non-task-related conversation improves the overall interaction. For example, whether a doctor chatting about weekend plans helps establish rapport with a new patient, or whether a salesperson asking where someone is calling from before diving into a pitch affects the likelihood of the sale.

These two ways of defining small talk are not the same thing—and the distinction matters when interpreting what the research actually tells us about small talk. Across both contexts, however, the research generally suggests that most people experience small talk positively, particularly when it serves a relational purpose. Even so, the findings are fairly clear on one point: I am not the norm. Most people—“normies,” to borrow from Wednesday, the Wednesday Addams Netflix show—tend to view small talk as all right. In professional contexts in particular, research often finds that brief off-topic conversation can help grease the wheels for relationship building and lead to more positive outcomes.

That said, there are important nuances in what makes small talk more or less effective.

• In off-topic professional conversations, factors like a consumer’s experience level and whether they are more relationship-oriented or exchange-oriented matter. Relationship-oriented consumers believe that forming some kind of bond matters to the transaction – imagine a Lowe’s customer always seeking the same salesperson because they’re familiar with the customer’s project and preferences. Exchange-oriented consumers, by contrast, don’t feel that a relationship matters—for example, I might pick out a drill for my husband and approach whichever salesperson is available. More experienced, exchange-oriented consumers tend to enjoy small talk less—and are less likely to experience better outcomes from it.

• Culture, gender, and neurodivergence also shape how small talk is perceived and valued. In professional settings, the research generally suggests that allowing the other person to set the tone matters— particularly when one party is in a service-provider role.

In summary, small talk appears to be mostly beneficial and rarely does more harm than mildly annoying people who are well-informed, task-focused consumers. These are individuals who often just want to get in and get out, without being “sold” or engaging in socially expected relationship building for interactions they don’t expect to extend beyond the point of the sale, drink at the bar, or prescription from the doctor’s office.

Or… wait. Is that me I just described??

Me No Small Talk Good

Another interesting finding in the research is just how bad people think they are at talking to other people. And, funnily enough, I actually don’t think I’m bad at it. Not even a little.

I tend to think I’m pretty good at conversation—and I don’t mind admitting that. More importantly, that confidence comes from practice. I don’t think I was always good at chatting; I wanted to feel less socially awkward, and I did something about it.

Again, many people feel differently. According to the research, most don’t consider themselves good at conversation at all. Several studies have found that people tend to blame themselves for awkward silences or worse. In one study, participants were asked to rate how good they were at everyday activities like cleaning and shopping or cooking. Most rated themselves good or great. But when asked to evaluate how good they were at “initiating and sustaining rewarding conversation at a cocktail party, dinner party, or similar social event,” very few thought they were good at this task.

Which is… kind of sad.

This kind of social miscalibration—believing you’re bad at conversation and blaming yourself for it—appears to stem from people assuming that others won’t care if they open up.

While I don’t disagree, I would add that this also looks like a broader issue of affect forecasting: people tend to be poor at predicting how future actions (like engaging in small talk) will actually make them feel. While they may anticipate discomfort, awkwardness, or rejection, the reality is often much more positive. Many people often feel better, more connected, or more at ease after engaging—even when they expected the opposite.

Full circle: when people believe they’re bad at something, they’re less likely to practice getting better—which means they don’t improve and miss out on opportunities that might actually be enjoyable.

In fact, when people are instructed to engage in small talk as part of an experiment, they often report liking it. Even introverts.

Okay, Okay… Can We Be Long-Talk Friends Now?

Research also offers a small glimmer of hope when it comes to small talk: it eventually ends. And, perhaps unsurprisingly, it tends to end in a few predictable ways.

Before we get into the endings, it’s helpful to pause on one framework that underpins much of small talk behavior.

Uncertainty Reduction Theory (URT), developed by communication professors Charles Berger and Richard Calabrese in 1975, proposes that people communicate with one another in order to reduce uncertainty—questions like: What kind of person is this? Can I trust them? Will I like working with, dating, or befriending them?

When I think about URT, I envision approaching the edge of a cliff. I suspect the view could be breathtaking, but I don’t want to rush forward. Instead, I inch closer—slowly, carefully—both feet firmly planted a few steps from the actual edge.

That’s how edging into a conversation with a new person often feels to me. It could be rewarding. It could be uncomfortable. And small talk is the cautious movement that lets you decide whether it’s worth stepping closer.

Small talk serves that purpose—and once that purpose is served, it comes to an end.

In professional settings, the most common ending is transactional: the interaction concludes. You get your coffee, buy the gadget, or finish asking your questions, and then you’re out the door. From the professional’s perspective, this is where small talk can play a useful role. Thinking again about URT, people can be nervous—about the topic, about trust, or simply because the situation is new. Brief small talk can help reduce some uncertainty and create a sense of safety. Once that safety is established, small talk naturally falls away.

In personal settings, the ending is often literal: people leave. A bus reaches its stop. A plane lands. Someone excuses themselves to refill a drink. Or, if things go well, the conversation can shift. What began as small talk about the weather or an event may deepen with a single curious question. At that point, the interaction moves into something else entirely—“deep-talk” territory.

A Small Conversation a Day Keeps the Doctor Away

An original—and still meaningful—goal of the (Less) Lonely Money Substack has been to help address the loneliness epidemic. And, as it turns out, psychologists and other medical professionals suggest that small talk may offer a low-stakes, potentially high-reward way of doing just that.

In Why Brains Need Friends, Ben Rein, PhD, discusses how doctors in the UK have begun prescribing social connection as part of the treatment for chronic loneliness—they literally encourage some patients to visit a bar or coffee shop, or even to just say hello to someone on public transit. There has even been a public campaign, Small Talk Saves Lives, encouraging people to check in with strangers who appear sad or distressed by asking simple questions like, “Hey, are you okay? Do you want to talk?”

This may seem small, but research has found that even brief interactions—like chatting with a barista—can help people feel more connected to their community. What if that conversation on the bus turned into a friendship? What if feeling more connected made someone feel a little safer, a little calmer? It all adds up.

And it’s here that I’ll admit a personal bias: while I may not like small talk, I do love the idea that a conversation—however small it starts—can bloom into something much deeper and more meaningful. Like an acorn growing into an oak, something small can become rooted, expansive, and beautiful.

Small talk may be where connection begins, but when it’s allowed to deepen, it can grow into something far more meaningful and satisfying—a sense of belonging, safety, and community that extends beyond the conversation itself.

One experiment of my own ties together the last few sections and serves as a natural introduction to what comes next. I force small talk on my students (or at least that is what they think I’m doing). Across many of the courses I teach, we play something called the “Question Game.” The rules are simple:

1. Students pair up (sometimes I assign partners, which can make it more fun and increase the impact).

2. Before the game begins, they write down how they feel on a scale of 1 to 10, where 10 feels absolutely wonderful, and 1 feels not great at all. (Almost no one writes 10; they are usually horrified or annoyed by this assignment. This initial score matters.)

3. Students then choose a question from a list of 52. Some are simple (“Would you survive a zombie apocalypse?”), others deeper (“What advice would you give your 16-year-old self, and would you listen?”). But they choose the questions they’re going to ask; no one is forced to answer something they didn’t select.

4. One student asks the other their chosen question. For the next 10 minutes, the only thing the student asking the question may do is ask follow-up questions. No “me too” stories. No personal anecdotes. Just explored curiosity. After 10 minutes, they switch roles.

5. After about 20 minutes total, students again rate how they feel on a scale of 1 to 10. Almost without fail, most students report feeling at least one point higher than when they began.

Many students initially think this assignment sounds horrible. How could they possibly talk to someone they don’t know well for 10 minutes about a random question? There’s often visible anticipation anxiety, which, not coincidentally, fits neatly with Uncertainty Reduction Theory. What will my classmate think of me? What will I think of them?

What they don’t know—at least not until after class—is that research from Paul Zak and Judith Glaser suggests something remarkable. After about seven minutes of receiving undivided attention (e.g., curiosity, interest, focus), the brain begins releasing oxytocin, serotonin, and dopamine—the very chemicals associated with trust, connection, and well-being. Which helps explain why my students’ post-conversation ratings almost always rise.

Said another way, the brain doesn’t seem to distinguish between “assigned interaction” and genuine attention. Students know the exercise is graded and that their partner was instructed to ask questions. And yet, that knowledge doesn’t cancel out the experience of being listened to.

In fact, many students note the nervousness they had as the questioner (and, by default, as the one carrying the conversation) went away after asking their first two or three questions. Once they settled into the curiosity about their partner, they stopped worrying so much about being funny or interesting and started enjoying the conversation. Curiosity begets curiosity.

What does this mean to you? Call someone you love and give them your undivided attention. Get lost in curiosity and the wonder of another person and their perspective. It is a gift worth giving and certainly a wonderful gift to receive.

Small Talk, Small Exposure Therapy

The moral of the story is this: in some ways, small talk functions a bit like exposure therapy for people who dislike it—mildly uncomfortable but not without its potential benefits. One particularly funny article I read while working on this piece came from Madeleine Aggeler, titled “‘It’s Incredibly Useful’: Why Small Talk Is Great.” In it, she references an earlier Wired article that made me spit out my water while reading. Madeleine writes:

“A 2016 Wired article titled ‘Small talk should be banned’ argued that idle chit-chat ‘does not build relationships and does not make us happier’, but persists because ‘we actively seek the lowest common denominator’. Instead, the authors suggest deeper conversation topics, such as: ‘What is your relationship with God?’ or ‘What is something you fear in life?’”

I agree with Madeleine when she follows this by saying that “all of this is wrong.”

As a brief counterpoint, I also read an article from The Guardian by Claire Eastham describing an experiment that came closer to using the deep-conversation prompts suggested by the 2016 Wired article. For a month, Claire asked people questions like, “What’s your star sign?” or “What was your art teacher like at school?” in initial interactions. Claire admits that jumping straight into the deep end doesn’t always go well—but then again, neither does small talk.

This brings me, inevitably, back to myself. I have a few close friends who find my aversion to small talk both funny and curious. One of them, I suspect, takes pleasure in introducing small-talk situations into our interactions—perhaps hoping that this a kind of exposure therapy might help me overcome my discomfort (though I think they also find my squirm entertaining).

Another friend regularly meta-cognates our conversations, pausing their set of “How are you? What’s new?” types of questions to ask me, “This sort of thing bothers you, doesn’t it?” or “Is it okay if I ask you about this—does this count as small talk in your book?”

I find both relationships meaningful, endearing, and genuinely humorous. I care that they care—even if they have different approaches to show it—because in both cases, it reflects a deeper, more meaningful connection.

All of which is to say: if you ever meet me in person, you’re welcome to start with a small-talk question. My only request would be that we don’t then stay there. Much like the question game with my students, ask me follow-up questions, and I’ll do the same for you. I find people and their lives so interesting, and I hope that once we get past the initial uncertainty-reduction dance, you’d find me interesting, too.

And if you also hate small talk, I’m totally cool with starting a conversation in the deep end.

Feeling connected is as essential as clean air to breathe. For some people, moving slowly is what makes connection feel safe. And small talk—although not my favorite—can bring about great things, creating a path that makes deeper moments possible.

As always, a special thank you to my editor Erica. She never small talks me and I am so grateful!

References for the Nerds

Aggeler, Madeleine. November 21, 2025. “‘It’s Incredibly Useful’: Why Small Talk Is Actually Great.” The Guardian. Accessed February 9, 2026. https://www.theguardian.com/wellness/2025/nov/21/why-small-talk-is-great.

American Psychological Association. September 30, 2021. “Getting Beyond Small Talk: Study Finds People Enjoy Deep Conversations with Strangers.” American Psychological Association Press Release. Accessed February 9, 2026. https://www.apa.org/news/press/releases/2021/09/deep-conversations-strangers

Association for Psychological Science. “Well-being is related to having less small talk and more substantive conversations.” ScienceDaily. ScienceDaily, 5 March 2010. <www.sciencedaily.com/releases/2010/03/100304165902.htm>.

Ariely, Dan and Kristen Berman. September 21, 2016. “Small Talk Should Be Banned.” Wired. Accessed February 9, 2026. https://www.wired.com/story/banning-small-talk/.

Ballard, Dawna I., Dron M. Mandhana, Yohanna Tesfai, Cristian Soto Jacome, Sarah B. Johnson, Michael R. Gionfriddo, Nataly R. Espinoza Suarez, Sandra Algarin Perneth, Lillian Su, and Victor M. Montori. 2024. “Unhurried Conversations in Health Care Are More Important Than Ever: Identifying Key Communication Practices for Careful and Kind Care.” Annals of Family Medicine, 22 (6): 533–538. https://doi.org/10.1370/afm.3177.

Eastham, Claire. October 22, 2025. “A Moment That Changed Me: I Gave Up Small Talk for a Month—And the World Came Alive.” The Guardian. Accessed February 9, 2026. https://www.theguardian.com/lifeandstyle/2025/oct/22/a-moment-that-changed-me-i-gave-up-small-talk-for-a-month.

Gillis, Kaytee. June 27, 2025. “Why Do So Many Dislike Small Talk?” Psychology Today. Accessed February 9, 2026. https://www.psychologytoday.com/us/blog/invisible-bruises/202411/why-do-so-many-dislike-small-talk.

Glaser, Judith. 2014. Conversational Intelligence: How Great Leaders Build Trust and Get Extraordinary Results. Routledge.

Hudak, Pamela L. and Douglas W. Maynard. 2011. “An Interactional Approach to Conceptualising Small Talk in Medical Interactions.” Sociology of Health & Illness. 33 (4): 634–653. https://doi.org/10.1111/j.1467-9566.2011.01343.x.

Knobloch, Leanne K. 2008. “Uncertainty Reduction Theory: Communicating under Conditions of Ambiguity.” In Engaging Theories in Interpersonal Communication: Multiple Perspectives. Edited by Leslie A. Baxter and Dawn O. Braithewaite. Sage Publications, Inc. https://doi.org/10.4135/9781483329529.n10.

Mehl, Mattias. July 3, 2018. “Replication Study Shows No Evidence That Small Talk Harms Well-Being” Association for Psychological Science. Accessed February 9, 2026. https://www.psychologicalscience.org/news/releases/small-talk-well-being.html

Rein, Ben. 2025. Why Brains Need Friends: The Neuroscience of Social Connection. Avery.

Sandstrom, Gillian M. June 11, 2019. “Small Talk Doesn’t Need to Be Meaningless: The Benefits of Talking to Strangers.” Gillian M. Sandstrom blog. Accessed February 9, 2026. https://gilliansandstrom.com/2019/06/11/small-talk-not-meaningless/.

UK Small Talk Campaign: “Small Talk Saves Lives.” Samaritans website. Accessed February 9, 2026. https://www.samaritans.org/support-us/campaign/small-talk-saves-lives/.

Webb, David. November 8, 2025. “The Power of Small Talk: How Casual Conversations Build Connection, Boost Mood, and Make Us Happier Than We Expect.” All About Psychology Substack. Accessed February 9, 2026.

Wiener, Hillary J.D., Karen E. Flaherty, and Joshua Wiener. 2022. “Making a Positive (or Negative) First Impression with Small Talk.” European Journal of Marketing. 56 (12): 3516–3544. https://doi.org/10.1108/EJM-06-2021-0460.

Wiener, Hillary J.D., Karen E. Flaherty, and Josh Wiener. 2023. “Starting Conversations with New Customers: A Research Note on the Moderating Effect of Experience on Responses to Small Talk.” Journal of Personal Selling & Sales Management. 43 (3): 195–206. https://www.tandfonline.com/doi/full/10.1080/08853134.2022.2128813.

Zajechowski, Matt. April 4, 2024. “Study Shows American Are Becoming Less Effective Communicators.” Preply.com blog. Accessed February 9, 2026. https://preply.com/en/blog/bad-communication-habits.

Zak, Paul. 2012. The Moral Molecule: How Trust Works. Dutton.

In our latest video conversation, Ashley and I broke down OARS—a powerful framework from motivational interviewing that’s honestly useful far beyond the therapy room. Whether you’re talking to clients about their resistance to your financial advice or trying to get your partner to open up about their day, OARS can transform how you connect with people.

What Is OARS Anyway?

OARS stands for:

• Open-ended questions

• Affirmations

• Reflective listening

• Summaries

While this framework comes from motivational interviewing, these four skills show up across virtually every effective communication approach out there. They’re not therapy—they’re just good communication. And here’s the thing: they work independently or together, in your professional life and your personal life.

Open-Ended Questions: Getting Beyond Yes and No

An open-ended question is one that can’t be answered with just “yes,” “no,” or a single word. Instead of asking “Is turquoise your favorite color?” (which gets you a simple yes or no), you’d ask “What’s your favorite color?”

The difference seems small, but the impact is huge. Open-ended questions invite people to actually talk, to share context, to give you information you didn’t even know to ask for.

Here’s what I see when I read advisor-client transcripts: lots of closed-ended questions. And I get it—they’re easier to formulate on the fly. But if you have a process, if you have a list of questions you typically ask clients, take a moment to review them. If most can be answered with yes/no or a quick fact, consider rephrasing.

Instead of “Have you started saving for college?” try “Tell me about your college savings plans.” You might discover that one kid isn’t planning to go to college at all—information that completely changes your planning approach.

The caveat: Sometimes closed-ended questions are exactly right. “How much is in your 401(k)?” deserves a number, not a story. The key is using open and closed-ended questions like a dance—a two-step, if you will. Open-ended questions to explore and build understanding, closed-ended questions to gather specific facts or gently close out one topic before moving to the next.

Also worth noting: some people get anxious with too many open-ended questions. If you notice someone getting flooded or overwhelmed, switching to some closed-ended questions can actually be grounding for them.

Affirmations: More Than Just Being Nice

Affirmations are acknowledgments of a person’s strengths, efforts, or courage. They’re honest compliments that build self-efficacy and hope.

“It took a lot of courage to share that with me.”

“I can see you’ve really thought this through.”

“I’m so glad you called me to talk about this before making a decision.”

These aren’t just pleasantries—they’re strategic. Affirmations build rapport and reinforce the behaviors you want to see more of. If you want clients to come to you before making big financial decisions, affirm them when they do it. “I really appreciate that you brought this to me first” tells them they did the right thing and encourages them to keep doing it.

Affirmations are also powerful for managing resistance. If a client calls wanting to dump all their cash into crypto (a totally random example), you could meet that with judgment. Or you could start with an affirmation: “It’s clear you’ve thought a lot about this. I appreciate that you’re calling to discuss it with me.” Now you’ve created space for a real conversation rather than a defensive standoff.

The money world is lonely. People don’t run around celebrating their million-dollar milestones with cake. But you, the financial advisor, could. You could acknowledge when clients have worked hard and reached their goals. They need to hear it, and it matters.

Reflective Listening: The Hardest Skill to Master

Full transparency: Ashley loves reflective listening. I find it challenging. It doesn’t come naturally to me, and when I try, it sometimes comes out as what I call “label listening”—just telling people who they are rather than reflecting what I’m hearing.

Reflective listening means paraphrasing what you’ve heard to demonstrate understanding. It’s not mirroring (repeating their exact words back robotically). It’s not taking over the narrative. It’s showing you get it.

Ashley’s go-to phrases include:

• “It sounds like you’re feeling...”

• “What I’m hearing you say is...”

• “So if I’m understanding correctly...”

The magic happens when you reflect back not just the content, but the thoughts, feelings, and actions someone shared. Then—and this is critical—you ask: “Am I getting that right?”

That question gives the client space to process their own experience. Sometimes they’ll say yes. Sometimes they’ll say no, even when you literally just repeated their own words back to them. And when they say no? That’s gold. That’s an invitation to go deeper, to clarify, to understand better.

Think of it this way: the client hands you a bouquet of information. You get to choose which flowers to hand back—which emotions to reflect, which behaviors to highlight, which strengths to affirm.

Summaries: Bringing It All Together

Summaries synthesize everything that’s been said. They’re hard to do well, and honestly, I don’t always get them right. But when done effectively, they help clients settle emotionally—taking the elevator down a floor, as Ashley puts it.

A good summary reinforces what’s been discussed and helps both you and the client figure out where to go next. It also gives you crucial brain space to think: Wait, we had an agenda. We were supposed to talk about estate planning. But clearly this crypto conversation is what needs to happen right now. How do I pivot?

Pro tip: Use your notes. There’s nothing wrong with glancing at what you wrote down and saying, “So we talked about this, you made these important points, you mentioned this concern. Is that right? And given all that, what feels most important to address next?”

And here’s permission you might need: it’s okay to pause. It’s okay to say, “I want to respond thoughtfully—do you mind if I take a second to think about where we should go from here?”

Why This Matters (Beyond Better Meetings)

OARS skills aren’t just about having better client meetings, though they absolutely help with that. They’re about helping people feel heard, understood, and empowered. They’re about navigating ambivalence—which is exactly where people sit when they call you before making a big financial decision.

And these skills work in your personal life too. Try them with your partner (though fair warning: too many affirmations in one day might make them suspicious). Try them with your kids. They will absolutely eat it up.

These are muscles that need exercise. If you’re not used to communicating this way, pick one skill and practice it. Notice what happens. Experiment.

Because at the end of the day, people aren’t fixed with logic alone. They need to feel something. They need to know that their decision feels right as much as it makes sense on paper. OARS helps you get there—in ways that build connection, trust, and real understanding along the way.

Welcome to this month’s (Less) Lonely Meetings drop—a practical toolkit designed to help you turn each (Less) Lonely Money article into real conversations that deepen trust, insight, and client engagement.

Inside, you’ll find two advisor-ready tools:

• Client Companion — a thoughtful newsletter you can send to clients and prospects, offering a new way to understand grief as something we live with, not something we get over.

• Meeting Ready Guide — a practical, non-scripted outline to help you sit with grieving clients with presence, patience, and compassion during your next meeting.

This month, we explore grief—not the sanitized, stage-based version we were taught, but the real thing. The version that doesn’t go away, that cycles and loops, that shows up in unexpected moments. The version that, when named honestly, teaches us how to love better and live more fully.

Many clients are grieving—the loss of a spouse, a parent, a job, their health, or even the life they thought they’d have. But grief is rarely named directly in financial planning conversations, even though it shapes every decision a grieving client makes.

As advisors, you’re often the person who shows up in the aftermath—the one who sits across from someone trying to navigate an impossible transition. These conversations require more than technical expertise. They require presence, patience, and the willingness to hold space for what can’t be fixed.

These moments are among the most meaningful in the advisor-client relationship. They build trust in ways that spreadsheets and projections never can.

Let’s begin.

Client Companion -- This Month’s Client-Facing Newsletter

Newsletter Title:

Living With Grief: Why It Never Truly Ends (And Why That’s Okay)

Best Used:

• Following the loss of a spouse, parent, or loved one

• During anniversary dates of loss or major life transitions

• When clients are navigating ambiguous loss (illness, estrangement, identity shifts)

• As a thoughtful check-in for clients you know are struggling with ongoing grief

Suggested Subject Lines:

• Grief Doesn’t End—But Life Grows Around It

• What No One Tells You About Grief

• Living With Loss: A Different Way to Think About Grief

Full Text (Copy/Paste into Email)

Living With Grief: Why It Never Truly Ends (And Why That’s Okay)

Most of us were taught that grief has stages—denial, anger, bargaining, depression, acceptance. We learned that if we just kept moving through them, the pain would eventually fade. We’d “get over it.” We’d find closure. We’d move on.

But that’s not how grief actually works.

Grief doesn’t follow a linear path. It cycles. It loops. It ambushes us in the cereal aisle, at 2 a.m., or during an ordinary Tuesday. It recedes for months and then crashes back in without warning. It’s less like a hallway we pass through and more like the weather—unpredictable, atmospheric, and never fully under our control.

Read more

When I started writing about death last month, I thought I was writing for and about other people—for Keena, the woman who initially asked me to write about death, about my brother who is currently dying, about conversations we avoid, and the language we’ve lost. But somewhere in the middle of researching palliative care and Viking burials and what makes a “good” death, I realized something uncomfortable: I was also writing about myself.

I am grieving.

Not just anticipating grief, not just worrying about future loss, but actively, presently grieving. Grieving my brother as he changes, yes. But also grieving my mother as she watches her son fade away—an identity shift I have seen reshaping her in real time for years.

There are also smaller griefs. I now recognize that I grieve the quiet evenings my husband and I used to have before kids. I grieve my 20-year-old body, which could eat anything, sleep for only four hours, and still function. I grieve the version of myself who stood at the precipice of learning in college, when everything felt possible and nothing yet felt heavy.

And here’s the confusing part: I didn’t want to call any of this grief.

In my head, grief looked like Marley’s ghost in A Christmas Carol—dragging chains, weighed down by grievances, bound to the past. Grief was catastrophic. Grief was for widows and orphans and people who had lost everything. Grief was not for someone like me, living a life I genuinely love, with a family I adore, doing work that matters.

But more than that, grief feels like fear. C. S. Lewis wrote after his wife died, “No one ever told me that grief felt so like fear.” And that’s exactly it. Grief destabilizes everything. It shakes the scaffolding we stand on. It threatens all the parts of life we use to orient ourselves: safety, predictability, meaning, control.

And I hate that. I hate feeling afraid. Fear makes me want to control things, to fix things, to solve my way out of uncertainty. But grief? Grief can’t be controlled. It can’t be fixed. It just is.

To call what I feel “grief” seemed melodramatic. Ungrateful, even—given how much I still have and everything I’ve had..

But the Roman playwright Terence wrote: Homo sum, humani nihil a me alienum puto. I am human, so nothing human is alien to me. I believe this. I’ve always believed it. And yet I resisted grief. I refused to name it. I shoved it into a dark, locked box and told myself that if I didn’t label it, it wouldn’t own me.

As it turns out, the opposite is true.

What we don’t name still owns us. Maybe more so.

And so this article is about something I’ve been avoiding my entire life: learning to live with grief, not after it. Learning that grief doesn’t have to be catastrophic to be real. Learning that I can miss something and love something at the same time. That I can grieve my quiet nights and still be deeply, genuinely grateful for the loud ones with my kids.

Grief, I’m learning, doesn’t cancel out gratitude or joy. It can exist alongside them. It doesn’t replace anything, really. It simply shows up and takes up space, commonly arriving with everything else.

If anything, it feels like another dialect of love.

And if I’m going to talk about money, relationships, and meaning—if I’m going to keep asking hard questions about how we live and die—then I need to be able to talk about this, too. I need to feel it and name it for myself.

So, let’s talk about grief. Not the sanitized, stage-based version we were taught. The real thing. The version that doesn’t go away, but that we learn to carry. The version that, when named honestly, might teach us how to love better, live more fully, and stop pretending we can control everything.

What Grief Actually Is (Not What We Were Taught)

For most of my life, I thought I understood grief; I’d learned about Elisabeth Kübler-Ross’s five-stage process: denial, anger, bargaining, depression, acceptance. You know the model. It’s tidy. It’s linear. It suggests that grief is something we move through—like a hallway—entering at one end, passing through sequences of burning coals and ice baths, and emerging reasonably intact at the other.

Except: no.

That’s not how grief works. Not for me. Not for anyone, really.

Here’s the thing many people don’t know: Kübler-Ross created those stages to describe the emotional lives of people who were dying, particularly those who were struggling to accept the reality of their own mortality. They were never meant to be a universal map of how all people experience death, let alone how those left behind process loss.

Even Kübler-Ross herself clarified that grief doesn’t follow these steps uniformly, the way people often interpret her model. People relate to death very differently depending on culture, belief systems, and personal experience. For some, death is feared and resisted. For others, it’s held with curiosity, acceptance, or even spiritual openness. Somewhere along the way, though, the stages jumped categories—from the dying to the bereaved—and became one of the most persistent misunderstandings in modern psychology.

Yet the model lives on—probably because we desperately want grief to behave. We want order. We want a map. We want to believe that if we just keep walking, the pain will eventually subside. Or at least that’s exactly how I feel. When I’m stressed or sad or apparently grieving, my default is to really, really, really want control. I was even trying to control whether I acknowledged grief at all!

But grief doesn’t work like that.

It cycles. It loops. It ambushes us in the cereal aisle or while we brush our teeth. It recedes for months and then crashes back in at 2 a.m. It’s less like a hallway we can pass through and exit, and more like the weather—unpredictable, atmospheric, sometimes violent, sometimes still, and never fully under our control.

There’s another myth embedded in the stages-of-grief model: that the goal of grief is to “get over it.” To resolve it. To achieve “closure.” To finally, mercifully, move on.

But here’s what actually happens, according to grief counselor Lois Tonkin: grief doesn’t get smaller or disappear over time—it never goes away. Instead, life grows around it, so the grief takes up a different, often smaller proportion of our lived experience over time.

Tonkin developed this insight from a conversation with a bereaved mother who drew her grief as a fixed circle inside a larger circle representing her life. At first, the grief filled everything—every breath, every thought, every ounce of attention. But over time, while the grief stayed the same size, the life around it began to expand. Her capacity for other things—her ability to hold joy alongside sorrow—grew larger around the grief.

Importantly, the grief didn’t shrink. It didn’t fade. It didn’t “resolve.” What changed was her life. It expanded to create space for joy, connection, and meaning, until the grief became something she could carry alongside everything else.

This reframing matters because it eliminates the pressure to “move on.” If grief remains, it doesn’t mean we’ve done anything wrong. Its persistence doesn’t mean that something is stuck or broken; instead, it could be evidence of having loved something deeply enough that even loss can’t erase the attachment. The goal isn’t to shrink grief. It’s to let life slowly expand around it.

To be honest, sometimes I think this reframing helps explain how I ignored my grief for years. It wasn’t catastrophic. It came in many small cuts—each loss subtle enough that my life quickly grew around it. That isn’t better or worse. Grief is brutal and takes many forms. But it’s worth noticing the different ways it can be experienced.

Another model that has helped me comes from psychologist Pauline Boss, who spent decades studying ambiguous loss—the kind of grief that doesn’t have a clean beginning or end. Boss noticed that many people never reach a point of “no grief,” especially when the loss is ongoing, unclear, or entwined with identity. Instead of waiting for grief to end, she suggested something radical:

We can hope and cope at the same time.

We can hope the pain softens and cope with the pain right now. We can wish things were different and still take the next small step in the world as it is. We don’t need to be “healed” to keep living or “ready” to continue. And we don’t need to be free of grief to make decisions, stay connected, or find moments of meaning, love, or joy.

I believe that if more people knew about and embraced this hope-and-cope model, much of the shame around grief would fall away—especially the pressure to move on according to some culturally acceptable schedule. The pressure to “get over it,” the guilt for feeling sad, the sense that struggling means we’re doing something wrong.

Boss’s framework offers a different message: we’re not behind or failing when we grieve. We can live with grief the way humans actually live with grief.

The Many Shapes of Grief

By this point, I’d already realized something I wish someone had told me years ago: grief isn’t just about death.

It includes death, of course. But it also includes every moment when someone we love becomes someone we no longer fully recognize. Moments when identity shifts. When the future once imagined quietly dissolves and a different one takes its place.

There are names for these kinds of grief, but the clearest is ambiguous loss—grief with blurry edges, grief with no clean beginning or end. In fact, anticipatory grief often carries that same ambiguity, because the loss is not always clear-cut and it can happen gradually, in real time.

Anticipatory Grief: Grieving Before Loss

This is the grief I’m currently drowning in: grieving something that hasn’t fully happened yet.

My brother Mike is dying. Slowly. And I am grieving him now—not just the future loss of him, but the version of him who is already gone. The healthy one. The one who existed before twenty years of illness rewrote his mind and his life.

Anticipatory grief is brutal because it doesn’t offer the sharp clarity of a single moment. There was no specific day I can point to and say, “Here. This is the day when everything changed.” Instead, the change is slow, cumulative, and exhausting. I started losing him in tiny increments, over and over again.

And people don’t always understand it. “But he’s still here,” they say. And he is. But I’m also already grieving the conversations we’ll never have, the milestones he’ll miss, the version of our family that will never exist.

This grief is real. It is heavy. It is valid.

Identity Grief: Grieving the Person We Were

Here’s another thing no one tells us when we’re experiencing anticipatory grief over a loved one who’s dying: we don’t just lose that person. We also lose the version of ourselves that existed in relationship with them.

I grieve my role as Mike’s older sister. Someone who understood him and protected him. I miss Mike as the eldest of my younger brothers, and his protective and helpful nature. I watch my mother grieve my brother in a way that’s reshaping her entirely. She’s not just losing a son—she’s losing parts of herself, too. She’s losing the future she imagined for him.

My mom says all the time: “I’m never happier than my saddest child.”

That sentence carries so much about my mother’s identity. It’s not just empathy—it’s identity. Her well-being is inextricably tied to ours. When my brother suffers, she suffers. When I grieve, she grieves—not just for us, but with us, as us. She can’t separate her emotional state from ours because motherhood, for her, isn’t a role she plays. It’s who she is.

That’s identity grief. And it’s one of the most disorienting forms of grief because it doesn’t happen to someone else—it happens to us. Our sense of self shifts. The story we’ve always told ourselves about who we are has to be rewritten.

Who am I if my mother needs care instead of giving it? Who am I if my brother’s illness erases the shared childhood that only we remember? Who am I without the role I’ve always held in my family?

These aren’t hypothetical questions. They’re the shifts I experience in real time.

The Small Griefs We Don’t Name

But here’s the thing I keep coming back to: grief isn’t always catastrophic.

I grieve my 20-year-old body. I loved that body. It was strong and resilient and required zero maintenance. Now I wake up with aches I can’t explain and have to actually to go the gym. I grieve the version of me who could stay up until 3 a.m. and still function. I grieve the ease of it all.

And that doesn’t mean I don’t love my body now. I do. I’ve earned every scar and wrinkle and soft spot. But I can hold both: gratitude for what is, and a quiet ache for what was.

I grieve the quiet evenings my husband and I used to have—long dinners, uninterrupted conversations, spontaneous plans. And I also deeply, genuinely love the loud evenings with my kids. The chaos and laughter. The sticky hands and bedtime negotiations. How my daughter says “I love you, Mama” like it’s the most important sentence in the world.

I can miss something and love something at the same time.

That’s what small griefs teach us: that loss and love are not opposites. We can carry both, learning to name the small griefs—the ones that don’t feel “big enough” to matter—which is actually practice for the big ones.

I can laugh about my belly now—the soft roundness that my kids gave me, and the stretch marks that map my life. I don’t know how long it will be before I can laugh about my brother.

What Actually Helps (Not Self-Help)

Shakespeare wrote: “Everyone can master a grief but he that has it.”

That line has stayed with me, because it rings so true. Everyone has advice for grief—until they’re actually living inside it. Then all the neat suggestions and well-meaning platitudes fall away, and you’re left with the raw, hard truth: grief is unmanageable. It’s unmasterable. It does what it does.

Once we’ve lived inside grief long enough to recognize its different shapes, we start to realize something both devastating and freeing: very little actually fixes it.

And maybe that’s the wrong measure, anyway.

Grief doesn’t work like a problem to be solved. Instead, it’s an experience that we all have to move through—with others when possible, alone when necessary. And there are things that help. Not because they eliminate grief, but because they make the weight more bearable.

The Four Tasks of Mourning (Worden)

Psychologist William Worden refused to talk about grief in “stages,” because stages suggest passivity—like grief is something that happens to us. Instead, he described tasks: active processes we do, consciously or not, as we learn to live with loss.

These aren’t chores. They aren’t linear. They’re simply ways of recognizing what actually happens inside us as grief reshapes our lives.

Task 1: Accepting the reality of the loss.
This doesn’t mean liking it or being okay with it. It means seeing what’s what. Our minds will flip between knowing and not knowing—talking about the person in the present tense one moment, catching ourselves the next. That’s not denial; that’s protection. Acceptance, here, is acknowledging that the world has changed, even when we hate that it has.

Task 2: Processing the pain of grief.
This is where the emotional weather rolls in—sadness, fear, anger, regret, numbness, shame. Grief has to be felt. Not all at once, and not dramatically, but honestly. Ignoring the pain doesn’t make it disappear; it buries it. And buried pain has a long half-life.

Task 3: Adjusting to a world without the person (or without them as they were).
This adjustment happens everywhere—externally (new routines, new roles), internally (our identity shifts), and spiritually (our beliefs about fairness, meaning, and safety are rewritten). We become someone new, slowly and often painfully.

Task 4: Finding a way to remember while continuing forward.
This task isn’t about replacing the person, forgetting them, or “letting go.” Instead, it’s about building a relationship with memory that allows the person to be carried forward without crushing us under the weight. Remembering might look like lighting a candle, telling their story, or saying their name, or finding small ways to honor their impact. The goal isn’t to move past the memory, but to make room for it while continuing to live our own lives.

Worden’s tasks don’t reduce grief or make it easier. But they do help normalize what feels unbearable. They remind us that grief is active—that survival often looks like continuing, honestly, one day at a time.

These tasks describe the internal work of grief, which rarely happens on its own. The people around us—and how they show up—often make the difference between being able to keep going and feeling completely overwhelmed.

Being Witnessed

This is the first and most essential truth: grief needs witnesses.

Not people who try to cheer us up. Not people who urge you to look on the bright side. Not people who tell their own stories over ours. What grief needs is someone who can sit in the presence of the pain without flinching.

David Kessler, a grief expert, writes that grief must be witnessed in order to heal—not in the sense of disappearing, but in the sense of being seen, validated, and held.

When people say nothing—when they avoid the topic or change the subject because they don’t know what to say—it can make grief sharper. The silence can feel like abandonment. It can make someone question whether the pain is real or, worse, whether it was allowed at all.

But on the rare days when someone simply says, “I’m here. Tell me what today feels like,” something might loosen. Maybe not much. But possibly enough.

Finding people who can witness grief in this way is important. And being willing to show up as this person for someone else—without trying to fix or fill the silence—is an act of love.

Talking about my brother and family with close friends is the most healing thing I have experienced on my path. I am so grateful to have had these conversations and, in some ways, look forward to future conversations.

Being Remembered

One of the most heartbreaking parts of grief is not only losing someone but losing the shared remembrance of them.

In my research, I came across the story of Karen, a mother whose son died. She described how the world quietly erased her son from conversation. No one spoke his name. No one remembered with her. That secondary loss—the loss of acknowledgment—became, as she put it, its own kind of violence.

Grief involves more than missing the person. It also means losing the world that once recognized our love for them. Moving on isn’t what helps here. What does help is someone willing to remember with us; someone who says, “Tell me something about him.” Or, “I remember when...”

Over time, it isn’t the loss itself that changes, but whether the memory is carried alone or shared. And having someone help carry the memory is often what allows grief to soften.

Being with my two other brothers, Marshall and Matthew, this year has been healing because we can talk about our childhood memories. Remembering Michael before all the changes and laughing about our time together as siblings is a gift.

Letting Others Help in Imperfect Ways

People often hesitate to show up for someone who is grieving loved ones because they’re afraid of “saying the wrong thing.” But most people don’t need perfect words. They need imperfect people who are willing to show up anyway.

Help can look like simple, ordinary things:

• Sitting in the room without talking

• Texting “Thinking of you today.”

• Sending a photo or memory

• Dropping off groceries

• Asking real questions instead of polite ones

• Acknowledging how strange everything feels

It doesn’t have to be profound. It just has to be real.

Small, Predictable Things

When grief destabilizes everything, small predictable things can become anchors.

A morning walk. A warm drink. A familiar routine. A favorite show. A task we can complete.

These aren’t coping strategies in the self-help sense. They’re small reminders that life still has some structure, even when everything inside feels like free fall.

That said, these things aren’t meant to replace grief or keep it at a distance. They can offer important support—like helping someone get through their workday—but grief still needs space, whatever that might look like: collapsing on the sofa, crying, playing the music our loved ones adored.

Ignoring it entirely doesn’t make it disappear, it only pushes it down, where it has a way of showing up later, heavier and often more painful than before. The work, over time, is learning how to live alongside grief—using small, steady anchors to make the internal work of adjusting and remembering more bearable, without pretending the pain isn’t there.

The goal is not to let these things become a distraction from the pain. Sometimes they are that and maybe we need that to get through the work of the day. But when you go home. Collapse. Cry. Get that warm beverage and your loved one’s favorite sweatshirt, put on music you love or they loved and have your grief. I write those words for me most of all. I am very good at ignoring and distracting my heart but this doesn’t make it any better. In denying my grief some space, I suffocate it only to carry its corpse around…maybe that is why I feel that chain analogy. You can’t kill it. I can’t kill it. I have to learn to live alongside it.

For Financial Advisors: Sitting With Grieving Clients

Financial advisors already know that grief isn’t just emotional. It’s financial, and it’s practical. It shows up in every decision the client now has to make alone, or differently, or with a weight they weren’t carrying before.

And most advisors don’t know what to say.

Here are some things I’ve learned—both from research and from living it—that advisors can do to connect with their clients:

Support grief with presence. Don’t rush to solutions. When a client is grieving, they don’t need their advisor to fix their grief. They need to be witnessed. Leading with presence, rather than planning, often matters more than finding the right answer.

That presence can sound like open, invitational questions such as:

• “What feels most important to you right now?”

• “What would make you feel supported today or as we work through this task?”

• “Is there anything you need to say or decide before we talk about the financial pieces?”

Name the grief. If a client has lost a spouse, going beyond “I’m sorry for your loss” can help. Naming what’s happening and acknowledging that it’s hard can be grounding (e.g., “This is grief. It’s going to be hard. And we can take this as slowly as you need.”). Saying the person’s name can matter, too. So instead of simply saying, “I’m sorry for your loss,” it can be more meaningful to say, “I am so sorry about Jim/Tom/Sarah; I miss them, too.” This isn’t just a loss; it’s the loss of someone they loved.

Normalize the non-linear process. Clients will forget things. They’ll make decisions and then second guess them. They’ll feel capable one day and completely undone the next. That’s not confusion—that’s grief. So patience, repetition, and clear follow-ups (e.g., sending pre- and post-meeting agendas and re-caps) can help create steadiness when everything else feels upside-down.

Remember them. For advisors who worked with the deceased spouse, sharing a brief story or memory about them can signal that they haven’t disappeared. This lets the client know that their love—and that relationship—is still visible.

Be imperfect. Advisors don’t need to have all the answers or right words. They don’t need to be a therapist. Being human, present, and willing to sit with discomfort often matters more than saying anything perfectly. Asking what support they need, and responding to that, can go a long way.

In moments like this, the relationship itself often becomes the intervention. Not the financial plan. Not the portfolio. The act of being present, of seeing the client, and not rushing them through one of the hardest things they’ve ever faced.

That’s what helps.

Living With Grief

By this point, the myths, the models, and the daily ache make something clear that’s rarely explained at the beginning.

Grief does not end.

But it changes. And so do we.

We learn to carry what once felt impossible. Not because the weight gets lighter, but because our capacity expands around it. We grow new muscles, new rituals, new ways of being in the world. We become people who know how fragile life is and how deep love goes.

And that knowledge, as painful as it is, is also its own kind of wisdom—less comforting, but honest.

I once came across a line describing grief as “love with nowhere to go,” often attributed to writer Jamie Anderson. That has stayed with me because it reframes grief not as evidence that something has gone wrong, but as evidence that something mattered.

So maybe grief isn’t something to get over at all, but something we can still learn from. It can carve us into people who know how to cherish what’s still here. It reminds us to pay attention, helping us recognize the sweetness inside ordinary days and find moments of connection even when life feels sharp and unpredictable.

And it can make room for us to keep loving—awkwardly, fiercely, imperfectly—in a world where loss is inevitable and love is still worth it.

There is no closure. There is no finish line to grief.

There is only this: a life that widens around grief, slowly, honestly, in its own time.

I started this piece by saying I didn’t want to be grieving. That I resisted the label, shoved it into a locked box, refused to name it.

But I’ve learned this: what we don’t name still has a way of shaping us.

So, I’m naming it now. I am grieving—for my brother, for my mother, for my quiet nights, for my 20-year-old body, and for the version of myself who didn’t yet know how heavy life could be.

And I’m also living. Fully, imperfectly, and with gratitude for what is and a quiet ache for what was.

I can hold both. We all can.

References for the Nerds

Boss, Pauline. 1999. Ambiguous Loss: Learning to Live with Unresolved Grief. Harvard University Press.

Dickens, Charles. 1843. A Christmas Carol. Chapman & Hall.

Kessler, David. 2019. Finding Meaning: The Sixth Stage of Grief. Scribner.

Kübler-Ross, Elisabeth and David Kessler. 2005. On Grief and Grieving: Finding the Meaning of Grief Through the Five Stages of Loss. Scribner.

Lewis, C.S. 1961. A Grief Observed. HarperOne.

Terence. 165 BCE. Heauton Timorumenos (The Self-Tormentor).

Tonkin, Lois. 1996. “Growing Around Grief—Another Way of Looking at Grief and Recovery.” Bereavement Care 15(1):10. https://www.bereavementjournal.org/index.php/berc/article/view/362

Worden, J. William. 2018. Grief Counseling and Grief Therapy: A Handbook for the Mental Health Practitioner. Springer Publishing, 5th edition.

I’m not trying to be harsh here, but there’s some fascinating research that challenges how we think about client relationships—and it has major implications for why your referral strategy might not be working.

Jeff Hall at the University of Kansas has studied how long it actually takes to develop different levels of friendship. The findings? It takes 50 hours of interaction to reach “casual friend” status, 90 hours to become close friends, and a whopping 200 hours to be considered best friends.

Meanwhile, research from Kitces shows that most financial advisors spend about two to five hours per year in actual client meetings. You’re not even at casual friend status, let alone the kind of friendship that naturally generates referrals based on “you’re my buddy.”

This isn’t meant to diminish the meaningful conversations you have with clients. It’s just to point out that your relationship with clients isn’t the same as their relationship with Bob, who they play golf with every week or grab lunch with regularly. And understanding this distinction is critical to fixing your referral problem.

The Three Big Referral Myths

After working with countless advisors and diving deep into the research, I’ve identified three common misconceptions that sabotage referral efforts:

Myth #1: “Because they’re my client, they’re basically my friend—so they’ll refer me.”

As we just covered, the math doesn’t support this. You’re not operating at the friendship level that makes casual referrals a natural byproduct of the relationship.

Myth #2: “I do a really good job, so I deserve referrals.”

Here’s the thing: doing a good job is literally your job. If you did a bad job, that would be a much bigger problem. But here’s what’s really interesting—research from e-money and Absolute Engagement shows that even among clients who say “I love my financial advisor,” only about 33% have actually given a referral. Satisfaction doesn’t automatically equal referrals.

Myth #3: “I ask for referrals all the time.”

But here’s the real question: What exactly are you asking for? Because there’s often a massive gap between what advisors think counts as a referral and what clients think counts as a referral.

The Referral Definition Gap

This gap is critical. Let’s say your friend Susan asks me, “Hey Megan, you know lots of financial advisors. Could you introduce me to somebody?” I might say, “Yeah, my partner’s husband Clayton is fantastic. You should call him!”

If you asked me later, “Have you ever given Clayton a referral?” I’d say yes, absolutely. I’ve told people how great he is.

But if Susan never actually calls Clayton, from his perspective, he never got a referral.

See the problem? This is on us as advisors to be clearer about what we actually want. Do you want an email introduction? A phone number? An invitation to lunch with the prospective client? A warm handoff? You need to articulate this explicitly.

How Referrals Actually Happen

Here’s what the data tells us: Most referrals don’t happen because the advisor asked. They happen because the client’s friend needed help and asked for a recommendation.

Research from Dimensional Funds and Julia Littlechild shows that referrals typically occur when someone in the client’s life says, “Hey, you seem smart about money—can you introduce me to your advisor?” or when the client is talking with a friend who mentions a financial challenge, and the client thinks, “You should talk to my advisor about that.”

The referral activity is happening because of something going on in the client’s life, not because you asked for it in your last review meeting.

So how do we bridge this gap?

The Benjamin Franklin Effect: Using Psychology to Your Advantage

There’s a fascinating phenomenon called the Benjamin Franklin effect. Ben Franklin discovered that when you do a favor for someone, you actually like them more—even if you didn’t particularly like them before.

This happens because of cognitive dissonance. Your brain goes, “Wait, why am I doing this favor for this person? I must like them at least a little bit, because otherwise why would I be helping them?”

When I ask rooms full of advisors, “Who likes to ask other people for favors?” basically no one raises their hand. Nobody likes asking for favors—it feels uncomfortable and vulnerable.

But then I ask, “Who likes being asked for a favor?” (Besides painting your house or picking you up from the airport—call an Uber, people.) Almost everyone’s hand goes up. Being asked for a favor feels good. It makes you feel valued, needed, important.

So here’s the strategy: Ask for referrals in the form of a favor.

The New Referral Script

Instead of: “Hey, my business runs on referrals. If you know anyone who might need help, I’d really appreciate it if you’d send them my way.”

Try this: “I’ve had a few clients tell me they’ve mentioned my name to people they know, which I really appreciate. But I’ve found that often those people don’t follow up—I think it can feel awkward to reach out to someone you don’t really know. So next time someone asks you about financial planning, would you be willing to bridge that gap and copy me on an email to them, or invite me to coffee with them so I can answer their questions?”

Notice what this does:

• It’s clear about what you actually want (an email introduction or invitation)

• It tells a story about why this matters

• It frames the request as a favor (”Would you be willing...?”)

• It’s an invitation, not a demand—they can always say no

Helping Clients Tell Their Story

Here’s another powerful strategy, courtesy of Julia Littlechild’s research with Absolute Engagement: Most people don’t know how to talk about their financial planning process. They haven’t practiced articulating their experience or the value they’ve received.

You can fix this by asking three simple questions in a client meeting:

Question 1: “In your words, what problem would you say we worked on together?”

They might say: “Well, I came in six months ago worried about sending my kid to Harvard, and you’ve really helped me figure that out. I feel like we’re on a good path now.”

Question 2: “Great! How would you describe what we actually did to address getting Sarah to Harvard?”

They might say: “You used your software to look at scholarship options, and we put together a plan for how much we needed to save. You organized all these different pieces into a monthly amount we could actually work with.”

Question 3: “Last question—what do you feel was the greatest impact from working on this together?”

They might say: “I’m not worried anymore. My kid’s going to go to the college she wants, and I’m not going to go broke in the process.”

Do you see what just happened? You’ve helped your client articulate their experience and the benefits they received—not in terms of returns or account balances, but in terms of peace of mind and emotional outcomes.

Now, when they’re at a party and someone says, “Yeah, I heard Sarah’s going to Harvard—how are you managing to pay for that?” there’s a much higher probability they’ll share their story in a compelling way. Because they’ve practiced. Because they have language for it. Because they’ve connected their experience to real emotional benefits.

Who Actually Refers (And Why It Matters)

Some interesting data points on who’s more likely to refer:

Women refer more than men. The research consistently shows this, likely because women tend to be more comfortable asking for help and discussing vulnerabilities within their relationships.

Clients who were referred are more likely to refer. If Susan referred Maria to you, Maria is much more likely to give you referrals than other clients. She’s experienced the referral process and it was positive, so she’s comfortable doing it herself. This means tracking how clients found you is crucial data.

The Power of Asking for (Other) Favors

Here’s a bonus strategy: Ask your clients for favors unrelated to referrals.

If your client has a rock-star CPA and another client needs one, ask: “Hey, don’t you work with that great CPA? Another client is looking for one. Would you mind doing me the favor of giving me their number so I can connect them?”

What does this do? It demonstrates that in this relationship, we ask each other for favors. You’re modeling the behavior you want. You’re normalizing it. And you’re showing that asking for help is just part of how you work together.

Plus, it builds likability. When people do you favors, they like you more. It deepens the relationship. It creates social capital loops where everyone feels good about each other and the work you’re doing together.

The Bottom Line

Referrals are the number one way financial advisors grow their practices, and it’s the least expensive growth strategy available. But we’re either not doing it effectively, or we feel so uncomfortable about it that we avoid doing it at all.

My hope is that understanding the psychology behind referrals—the friendship hours, the Benjamin Franklin effect, the importance of clarity and story—gives you a new framework that feels less icky and more authentic.

Because ultimately, this isn’t about manipulation. It’s about building genuine social capital with people who trust you enough to let you help them with their money. And when you do that well, referrals become a natural extension of the relationship you’ve already built.

Welcome to this month’s (Less) Lonely Meetings drop—a practical toolkit designed to help you turn each (Less) Lonely Money article into real conversations that deepen trust, insight, and client engagement.

Inside, you’ll find two advisor-ready tools:

• Client Companion — a thoughtful newsletter you can send to clients and prospects, opening the door to conversations about death, legacy, and what matters most at the end of life.

• Meeting Ready Guide — a practical, non-scripted outline to help you hold space for these difficult yet meaningful conversations in your next 30-minute meeting.

This month, we explore one of the most difficult topics in financial planning: death. Not the logistics—though those matter—but the human experience of dying, the language we’ve lost for talking about it, and how we can help clients approach their own mortality (or that of a loved one) with more agency, clarity, and grace.

Most clients avoid these conversations—not because they don’t care, but because they don’t know how to start. They lack the language, the permission, and often the emotional safety to name what’s happening or what they want. As advisors, we’re uniquely positioned to create that space.

These conversations are some of the most intimate, meaningful, and trust-building moments in the planning relationship. They help clients feel seen, heard, and supported—not just in their financial lives, but in their full lives.

Let’s begin.

Client Companion - This Month’s Client-Facing Newsletter

Newsletter Title:

A Good Death: Reclaiming the Language We Need to Talk About Dying

Best Used:

• During estate planning reviews or legacy conversations

• When a client or their loved one has received a terminal diagnosis

• In advance of or following a health crisis or aging transition

• As a thoughtful touchpoint for clients navigating end-of-life decisions for aging parents

Suggested Subject Lines:

• What Makes a Good Death? (And Why We Need to Talk About It)

• The Lost Language of Dying—And How to Reclaim It

• Why Talking About Death Can Be an Act of Love

Full Text (Copy/Paste into Email)

A Good Death: Reclaiming the Language We Need to Talk About Dying

Most of us don’t talk about death—not really. We plan around it. We defer conversations about it. We use softer words like “passing” or “end of life” to avoid naming it directly.

But death, like money, requires a language we’ve largely forgotten how to speak. And that silence—however unintentional—can leave us feeling unprepared, disconnected, and alone when death does arrive.

Read more

Until recently, I might have even said I was grateful that my encounters with death have been brief and bearable; that I don’t know death. I’ve lost both my grandfathers and one grandmother. Those were hard. But for most of my life, death has stayed at a palatable and expected distance, arriving only through statistics or in the stories of others.

But I can no longer say that this is the case. The distance of death has only been an illusion. My brother is dying. And has been for twenty years now. Throughout his illness, I have been learning, painfully and incrementally, what it means to live alongside death. His illness has introduced him—and me, along with the rest of my family—to a thousand small endings: each break; each medication, therapy, and treatment; each redefinition of what “better” means with each ending.

And so, from here, with this proximity of death in my own life, this is where I will begin this month’s article. Sorry, this one is not going to be about love; at least not in the Valentine’s Day way.

I think, maybe, this continual dust-up with helplessness, anger, fear, sadness, and whatever word would mean something so entirely confusing and unfair to you is, in some way, why I’ve always been drawn to unanswerable questions. Sitting with death and the really tough questions and situations that life hands us—that is, at least in part, why I do what I do today. I think I’m driven to research things like how to talk about money or what to do when someone tells you they’re dying because it’s a salve. It’s a way for me to search for clarity and closeness—sometimes consciously and sometimes, perhaps, subconsciously—in a world that seems to keep challenging my family, my faith, my beliefs, my ethics.

You might be thinking, What’s happened? Doesn’t Meghaan usually write about money? Yes. I do. But death is a lot like money in that talking about both requires what can feel like a dead or forgotten language. We often struggle to get to the heart of what really matters in both death and dollar conversations. For example, estate plans don’t just address what’s left as an inheritance; they can help pass down heritage—a description I once heard from an advisor. But how do you talk about that? Where do you start?

I’ve lived abroad in a few different countries where I lacked fluency in the local language, so I know how disorienting it feels to want to say something vital and not have the words. It’s a lonely silence—because you can still hear yourself explaining and sometimes screaming—unable to make yourself understood. And I’ve begun to wonder if talking about death relies on lost language—it’s something we used to speak about openly, ritually, even communally; but now we often struggle simply to name it.

Moreover, while I’m not sure if money was ever a topic people discussed with fluency. Death fluency was something we did have; there was once a time when the language of death was spoken in households more commonly. But, like old dialects that evolve and eventually fall away from disuse, our ability to talk about death had been replaced by our current vocabulary—often a sanitized, medicalized, outsourced version of the original. We simply avoid the conversation because, in modern life, discussions about death feel nonobligatory—or at least deferrable, like the decision to begin withdrawing Social Security or not. But these are really difficult discussions; talking about the “what ifs” are scary and painful. And often they’re just easier to defer to another time down the road. We’re too busy and caught up in “the present” to be bothered to face all of those questions right now.

Furthermore, living longer has become a serious business. We invest in it, extend it, measure it in years and percentages. But ultimately, no matter how much we have hopes for or invest in living longer, each of us will someday die. And that reality raises a harder set of questions: Is death truly an “optional” conversation? Do we defer it as long as possible simply because we’re scared to face our own mortality? Here’s another hard question—and this one might sound weird—but is there such a thing as a “good” death? What would it mean if we talked about death more openly? How might that shape our lives and the time we have left?

And what, then, makes life precious? Is it the simple fact of being alive, or the parts of life that feel meaningful? At what point does the preciousness shift, people get tired and pain replaces precious, and how do we talk about that before—and after—it happens?

Without the words, it’s difficult to answer these questions. I’m searching for that language. A way to talk with—not around—the people we love who are dying. To understand what they still find precious, and what they might want for a good death—however they may define it. I believe that if we can understand a language that lets us consider these questions, we can indeed plan for a good death in the same way we plan for all ends and goals we care about: deliberately, tenderly, and together.

I can’t tell anyone how to have a good death, nor define what that even means. I can’t make the conversations that I’m going to suggest feel good or easy; I still find them extremely hard. But I think I can share a few starting points, and encourage curiosity; I think both life and death deserve our curiosity.

The Lost Language of Death

To understand why this language feels lost, it helps to look at how differently we considered death in the past, when it was more familiar and, perhaps because of that, more openly discussed. People died earlier (we live longer now) and more often (child mortality was higher). I’m not suggesting that this was a better time; I’m grateful mortality is lower and we have more years with those we love.

Yet, because death was more common and closer at hand, we spoke it—through gestures and rituals, through songs, prayers, and stories told at bedsides. We saw the bodies of our loved ones. Families prepared the home for death much like they prepared for a birth. Today, though, we’ve professionalized and outsourced much of the work of dying. In the process, we’ve traded some of our shared language for a lighter, less labor-intensive approach.

Again, I don’t blame anyone for this—death is really hard. But this shift has consequences. Hospitals not the home are the liminal space between life and death. Words like hospice, palliative, and comfort care soften the truth. And I get it—death is scary. Still, we’re left facing an imbalance where there’s a focus on clinical precision to prolong life, but very little shared vocabulary for how to accompany someone through the end of it. We have professional acumen for discussing investing and giving, but far fewer words for memorializing and naming what matters most in our most vulnerable moments.

And here’s something that’s as true with money as it is with death: when we aren’t given the space or permission to name what’s happening, we deny its reality—even when it remains very, very real. We replace conversation with optimism, planning, or silence. We defer the hardest truths until they can no longer be spoken.

Rose, a death doula, CFP professional, and a wonderful woman I interviewed for this article, once wrote to me after I’d told her about my brother. She said that death comes to all of us both slowly and all at once, and that most of us—those who are dying and those who love them—must face a thousand small deaths before the final one arrives.

Loss of independence.
Loss of work.
Loss of memory.
Loss of identity.
Loss of the person we used to be.

We rarely give ourselves or each other the room to grieve these secondary losses, Rose also said, and that often leads to denial about what’s happening now and what’s coming soon. Her words have stayed with me, but maybe not in the way that you might expect.

I try to see these tiny deaths—these moments of disappearance—as conversational invitations. Chances to begin speaking the language again. To ask gently, what remains important, what still feels meaningful, and what they—and we—need to say now.

The Stoics have a phrase for this kind of awareness: memento mori—remember that you too must die. It wasn’t meant to darken life, but to make it deliberate. Still, I’m not a Stoic, and I actually feel a bit uncomfortable even sharing this phrase.

Stoicism, for me—and I know people will disagree—is the very thing I’m trying to push away from. Don’t be stoic. This shit hurts. Pretending it doesn’t or ignoring the pain in service of what “needs” to happen, acts as a pacifier. It placates the parts of us that make us most human: the hard, big, scary feelings that must also be processed alongside the practical tasks that still need to be done.

In a very simple sense, Stoicism asks us to sanitize or circumvent the hardest parts of being in relationship with others—the emotions we feel, the emotions they feel, and the emotions we collectively carry because we live in relation to one another.

This reminds me of my discomfort with the “Let Them” philosophy popularized by Mel Robbins. To me, it feels too self-centered, too focused on the individual: Can’t change how a person is or what they think? No matter… just accept it and move on. Yet, that’s simply not how love works. Anymore than the Stoics believing or wanting us to be able to set aside our emotions just to get done what needs to be done. You can’t just move on from or ignore everything. Some of us, when it comes to the people we love, never want to move on at all. While the Stoic or “Let Them” mindset may feel freeing in some ways, it’s also fleeting. We live in community with others, and part of that life is learning how to stay with people and understanding them—even when we don’t like their choices.

It’s also worth remembering that much of Stoic writing emerged in a very different world. Marcus Aurelius—one of Stoicism’s most influential figures (and someone I doubt ever intended his private journals to become traditional works of philosophy)—was a General. He ordered men to their deaths and had to live with the consequences. He was navigating total chaos and trying to think clearly when so much was already lost. Maybe there’s something to that context and the need for Stoicism in moments like those. I don’t know. That’s another post for another day.

But setting all of that aside, memento mori can still serve a purpose. It calls us to keep our priorities sharp. Recovering the language of death is not about morbidity at all. It’s about meaning. And if we don’t already have the words available, meaning can only emerge in the attempt to speak, to listen, and to stay present.

If we no longer share a common language for dying, though, how do we begin to speak it again?

Learning to Talk About Death (Again)

I didn’t share this earlier, but I never planned to write about death. I was asked to do it. Keena Pettijohn—a firecracker of a woman with her own blog and following—asked me to write about death. I didn’t know what I was going to say.

Keena is in her seventies, wise and pragmatic, with the kind of curiosity that refuses to shrink from hard things. After our phone conversation, I had the sense that she could see her horizon and wanted to find a way to talk about it—with her family, her community, and herself.

Her request felt like both an honor and a burden. Death, again, is not a topic I had sought out, and being asked to write about it felt like being handed something fragile. We lose people we love all the time. Advisors lose clients—it’s inevitable if you do this work long enough—but do we ever talk about how to talk about it? How often do we help people talk about death while they’re still here? Not about beneficiaries, estate documents, or grave plots, but about the meaning of leaving, about what a “good death” might look like.

At first, I did what I always do when I don’t know where to begin: I read. So I started reading about death, death doulas, hospice, medical ethics, Viking burials, and Christian ideas of angels and peace. But books can only take you so far. What I really needed was a conversation… go figure! 

Meeting Rose, interviewed for this piece, was serendipitous. Rose, again, is both a death doula and a CFP professional, which felt like finding a translator fluent in both languages I care about—money and mortality. Talking with her was unexpectedly healing.

Rose told me that the death doula movement was modeled after the birth doula movement—both born from the same impulse to reclaim agency over transitions that are profoundly human and deeply personal. A birth doula helps bring life into the world on the terms of the person giving birth. A death doula helps a person leave it on their own terms.

That parallel mattered to me. It gave me hope that I might be able to write about this topic, which still feels somewhat foreign. A good death, like a good birth, isn’t defined by the absence of pain or some other medical consideration; it’s defined by agency, by care, by having the experience honored and owned by the person living it.

Even so, there are complications. Rose pushed me to think more carefully about who gets to define a good death—the doctors, the family, the culture, or the person dying? We talked about how culture, class, and religion shape our ideals of peace. She shared that hospice, in its current form, is often very white, middle-class, and Christian—a space filled with angels, harps, and soft light. But not everyone wants that. Some people want home deaths, forest deaths, quiet deaths with one or two people they love—and some want to die alone.

What struck me most was how ordinary her stories were—ordinary in the sense that they belonged to real people, wanting ordinary things, with ordinary curiosities and fears. We may not talk about it often, but in the end, many of us share the same questions and needs.

What Makes a Good Death?

For some, a good death means one without pain. For others, it’s about control—getting to decide when, where, and how. For others still, it’s about connection: being surrounded by people who love you, being remembered, being known.

There isn’t a single right answer because there isn’t a single right way to die. Death, like life, is deeply personal, but also unavoidably cultural. We inherit ideas about what dying should look like, often without realizing it.

In Viking culture, for example, a good death was one met in battle—a life spent, a story sealed with courage. In many Christian traditions, a good death is quiet and reconciled, the soul prepared and the body at peace. In modern medicine, a good death is often measured in comfort, cleanliness, and control—hospital rooms and hospice beds scrubbed of the messiness that living and dying both contain.

Each version reflects something we value: strength, faith, order, serenity. But what if a good death is simply one that reflects the person living it?

When we talk about “good deaths,” then, maybe we’re really talking about good endings.

The difference is subtle but important: a good ending still belongs to the person whose story it is. We can’t write it for anyone else; but we can help them finish it on their own terms. Our stories move backward and forward; we want continuity.

That’s what I keep returning to in my own conversations with my brother. What makes his life meaningful now? What remains his, even as things change? These aren’t easy questions to ask, but I’ve learned that not asking them doesn’t make them go away, it only makes them lonelier.

So maybe a good death isn’t something we can define, but something we can listen for.

It shows up in the way someone describes what they still want. In small hopes and last preferences—the music they’d like played, the words they’d like said, the room they’d like to be in. And in our willingness to hear them, and to say, simply, tell me more.

How to Talk to the Dying

When I first started reading about death, I was struck by how much the guidance for talking about dying resembles the best advice for talking about money. Both require honesty, humility, and timing. Both bring up fear and vulnerability.

And both tend to go badly when we begin with information instead of meaning.

In Being Mortal, Atul Gawande tells the story of a palliative care physician who warned him against becoming “Mr. Information.” Facts are necessary, but they’re not what create meaning. When people are faced with hard news, they rarely need more data; they need help understanding what the data means for them.

That’s why palliative care doctors use a simple but powerful technique known as ask–tell–ask. They begin by asking what someone already knows, or what they want to know. Then they tell—the truth, the medical facts, the likely path ahead—but briefly. And then they ask again: What do you make of that? What worries you most? What matters most now?

This way of speaking doesn’t fix anything, but it keeps the conversation alive and connection front and center. It makes space for the dying person’s own language. I think about this as a kind of conversational stewardship. When we sit with someone who is dying, we’re not there to manage their expectations or correct their optimism. We’re there to help them retain ownership of their story.

That means listening more than talking, asking rather than assuming, and being brave enough to name what’s real without stealing hope. It’s also about timing. The best time to talk about death isn’t only when it’s imminent. It’s often in the smaller deaths along the way—the moments of change, loss, and redefinition that Rose described. Those are the openings where we can ask:

• What feels important to you right now?

• What do you still want to do, to say, or to leave behind?

• What would help you feel at peace if today were one of the last good ones?

I don’t know how to make these conversations easy. I only know that when we avoid them, the person who’s dying often feels more alone with what they’re facing.

When someone we love is dying, they are still living. They are still teaching us how to be present, how to be curious, how to honor what matters.

And so, the work isn’t really to talk about dying—it’s to talk about them.

When Keena and I first spoke about writing about death, she kept returning to the same few questions:

What do you want said about you? Who do you want to say it? What stories do you want told?

They sound simple, but they’re anything but. Each question invites reflection—not on death itself, but on the meaning of a life. They ask: How do you want to be known? And What do you want to leave in the minds of others—and in the stories they carry forward?

These conversations are hard. They touch the parts of us that want to keep fighting, that don’t want to be misunderstood, that are afraid of being forgotten—or afraid of not being finished.

My great-aunt was a nurse her entire life, helping people live. Now, she has a bad heart, constant pain, and she often says she’s tired—tired of hurting, tired of doctors, tired of waiting for the next episode. She doesn’t speak of death as giving up; she speaks of it as wanting the pain to stop. Listening to her, I’ve realized that part of talking about dying is learning not to argue with someone’s threshold for suffering. It’s more about staying with their experience, even when we don’t share their conclusions or feel ready to agree with them.

I also think about Daniel Kahneman, the psychologist and father of behavioral economics, and his own end-of-life decision—to die before reaching a point where he no longer felt like himself. Kahneman helped the world understand the peak-end rule—the idea that we remember experiences by their most intense moment and their ending—and he believed that how we end matters as much as how we live.

So how do we help someone find language for that? Not to steer their choices, but to help them name what still matters.

The questions that follow aren’t meant to be asked all at once, or even always out loud. They’re meant to help you find your own entry point into these conversations—with someone you love, or perhaps, one day, with yourself.

20 Questions for Talking About Dying

Memoriam and Story

1. What do you want said about you—and who do you want to say it?

2. What stories do you hope people will tell others about your life?

3. How do you want to be remembered by the people who love you most?

4. Is there something you hope people will learn from your life—or from your death?

5. What feels unfinished that you’d like to complete, name, or pass on?

Meaning and Values

6. What has made your life feel meaningful?

7. What still feels meaningful now?

8. What parts of life are you most grateful for?

9. What values have guided you—and do they guide how you want to die?

10. What do you hope will live on in others because of you?

Agency and Autonomy

11. What would help you feel at peace if today were one of your last good days?

12. Are there experiences you still want to have, even small ones?

13. What kind of setting would make you feel most comfortable in the end—home, outdoors, with others, or alone?

14. What do you want control over, and what are you willing to let go of?

15. Who do you trust to speak for you if you can’t speak for yourself?

Connection and Closure

16. Who do you want nearby—or not—when the time comes?

17. Are there words you still want to say, or hear, from someone?

18. Is there forgiveness you want to give or receive?

19. What rituals, music, or comforts would make your last days or hours feel like yours?

20. What would a “good goodbye” sound or feel like to you?

These questions aren’t a prescription. They’re just ideas with which to practice. You don’t need to have answers ready—no one does. What matters more is the willingness to stay in conversation. When we avoid talking about death with those who are dying—and in some way, that’s all of us—it doesn’t make death disappear. It often just deepens the loneliness of those who are already facing it.

Talking about death can be one of the most intimate ways we can honor life. We do it to understand—not to fix anything or change anyone’s mind. It tells them that their experience, their story, and what they care about still matter—right up to the very end, and even beyond.

Toward a Good Death

So, what might a good death look like—for you? For me?

I don’t think there’s one answer, and maybe that’s the point. Every conversation, every loss, every small death reshapes what “good” even means.

What I do know is that talking about death can make us feel more prepared, more attuned, and sometimes more at peace when it does happen.

And yet, even with preparation, it will still hurt. It’s meant to. Grief is evidence of having loved. The psychologist Lois Tonkin once described grief not as something that fades, but as something we grow around. The grief stays the same size—it’s our lives that widen.

That widening—that slow, painful stretching—is the work of living after the death of someone we loved. I’ll write more about that next month, because this piece isn’t about grief. It’s about what comes before it—the conversations that help us meet death with some measure of agency and grace.

A poet I follow once wrote, “Autumn/fall is the time when dying things are allowed to be beautiful.” Maybe that’s all any of us can hope for: an ending—however near or far—that can be beautiful, because it honestly reflects who we were, what we gave, and how we lived.

A good death, like a good birth, is not something we plan for someone—it’s something we plan with them. It’s the culmination of a life that has been witnessed, expressed, and shared.

And maybe, when our time comes, the best any of us can hope for is what West African spiritual teacher Sobonfu Somé called a cleansing—a reclaiming of the spirit. To die not untouched by grief or fear, but known.

Postscript

Voltaire was once asked on his deathbed if he renounced the Devil. He replied, “Now is no time to be making enemies.” I’ve always loved that—equal parts wit, wisdom, and acceptance. It’s not denial; it’s readiness.

If you want to learn more about what it means to prepare for death, accompany someone who is dying, or simply talk about it, here are a few thoughtful places to begin:

• PALS (Professional After Life Services): A network offering practical and emotional support for end-of-life planning—from sorting personal effects to guiding family conversations.

• National Home Funeral Alliance: Resources for those who wish to die or care for loved ones at home, restoring intimacy and choice at the end of life.

• Death Doulas (End-of-Life Doulas): Certified practitioners who help individuals and families navigate the dying process, offering presence, memorial projects, and emotional care.

• Palliative Care and Hospice Care: Medical and supportive services that prioritize comfort, quality of life, and relief from pain and distress at the end of life.

References for the Nerds:

Here is a list of the books I read while working on this piece… there are many more though, and that is a good thing:

· A Beginner’s Guide to Dying by Simon Boas

· Being Mortal: Medicine and What Matters in the End by Atul Gawande

· When Breath Becomes Air by Paul Kalanithi

· Advice for Future Corpses (And Those Who Love Them) by Sallie Tisdale

· The Art of Dying Well: A Practical Guide to a Good End of Life by Katy Butler

These are just a few ways to begin speaking the language of death again—because silence, in the end, is the one thing that doesn’t serve us.

Happy January!

Last month I thought I had posted a chat with where we discussed buzzwords and what those look like as actual skills…but in my flu induced haze. Well. That just didn’t happen. As such, here it is in January. The real one this time, enjoy!

If you’ve ever cringed at phrases like “hold space,” “witness,” or “show up,” you’re not alone. They float around the worlds of therapy, coaching, and now financial planning—well-intentioned, but often fuzzy. In this discussion, Ashley Quamme and I tackle what these ideas actually mean and how advisors can turn them into practical, professional behaviors.

At its heart, “holding space” isn’t about being mystical or passive. It’s about pausing before advising; resisting the urge to rush toward solutions. We want to let go of, at least for a bit, the compulsion to “right the ship.” Because, believe it or not, most clients don’t immediately need a fix; they first need to feel heard, understood, and safe.

We explain that “holding space” can sound like:“We’ll get to the strategy, but before that, I’d like to understand what’s going on more fully—would that be okay?” That small, structured pause brackets the conversation, gives clients permission to process, and signals that the advisor is confident enough to stay curious.

Ashley adds that clients are always—often unconsciously—asking one question: Are you there for me? Her favorite model, A-R-E, comes from emotionally focused therapy: be Accessible, Responsive, and Engaged. Responsiveness doesn’t mean leaping into action; it means attunement—acknowledging feelings, not just numbers.

Together we unpack the three H’s from Charles Duhigg’s Super Communicators: every conversation is really a request to be Heard, Hugged, or Helped. Advisors usually skip to “help.” But if you meet the first two needs—listening and emotional support—the technical advice that follows lands with far more trust.

We also touch on co-regulation—the science of calm being contagious. When advisors stay grounded and curious, clients mirror that steadiness. Like a 911 dispatcher who asks questions instead of panicking, curiosity lowers anxiety and keeps thinking flexible.

Finally, “witnessing” isn’t woo-woo; it’s a specific skill: reflecting, summarizing, and validating without rushing to reframe or sugar-coat. Sometimes it sounds as simple as, “That sounds really hard—thank you for sharing that.” Those micro-moments of empathy make advice more actionable and the relationship more durable.

Key Take-Aways

• Translate “woo-woo” into observable behaviors. Define what “holding space” looks like.

• Pause before advice. Curiosity beats correction.

• ARE you there for me? Accessible • Responsive • Engaged.

• Heard → Hugged → Helped. Don’t skip straight to the fix.

• Co-regulate. Your calm helps clients think clearly.

• Witness, don’t rescue. Reflect, validate, and resist toxic positivity.

• Woo-woo ≠ soft. These are hard, technical communication skills that make financial advice land.

Welcome to this month’s (Less) Lonely Meetings drop—a practical toolkit designed to help you turn each (Less) Lonely Money article into real conversations that deepen trust, insight, and client engagement.

Inside, you’ll find two advisor-ready tools:

• Client Companion — a reflection-first newsletter you can send to clients and prospects, introducing the idea that small financial experiments can build confidence and clarity.

• Meeting Ready Guide — a practical, non-scripted outline to help you bring experiment-based conversations into your next 30-minute meeting.

This month, we explore a powerful shift: moving from prediction to participation, from pressure-filled goals to safe-to-fail experiments.

Most clients don’t struggle because they lack information or discipline. They struggle because they don’t know how to fit what they want into the texture of real life. Experiments—small, intentional, reversible tests—help bridge that gap.

These conversations are some of the most enlivening, constructive, and hopeful in planning. They help clients learn what actually feels right, rather than guessing or striving for perfection.

Let’s jump in.

Client Companion – This Month’s Client-Facing Newsletter

Newsletter Title: Skip the Resolution—Try a Test Instead: Why Money Experiments Help Us Grow

Best Used:

• During annual reviews (especially Q1 or pre-year-end planning)

• With clients who feel stuck or hesitant (e.g., underspenders, overspenders, self-critical planners)

• During retirement or identity transitions

• When clients are setting goals but feel tired or overwhelmed

Suggested Subject Lines:

• A Better Way to Change This Year

• Why Small Experiments Build Big Confidence

• What If You Tested Your Way Forward?

Full Text (Copy/Paste into Email)

Skip the Resolution—Try a Test Instead

Every January, we feel the pressure of goals. New habits. New budgets. New expectations.

We imagine the year as a straight line: decide → execute → succeed.

But real life rarely works that way. Here’s an alternative approach that’s kinder, easier, and more effective: Try an experiment instead of setting a goal.

An experiment is different from a commitment. It’s temporary, bounded, and designed to help you learn something—about your preferences, your limits, your values, your future self.

It lowers the stakes.
It raises curiosity.
And it replaces pressure with permission.

Why Experiments Matter

Psychologists, therapists, and change management scientists have found the same thing: small, reversible tests help people grow far more reliably than rigid long-term goals.

A money experiment might look like:

Read more

When I’m facing a decision that feels big: career, relationship, family, anything carrying emotional weight...I tend, like most people, to want to get it right. My version of “getting it right” is to read the research, make the pros-and-cons lists, imagine every possible future, and force my husband to listen to all of them. I get a bit panicky, to say the least. But I try not to get stuck there. The way I do that is through experimentation, by telling myself that I can try something small, learn, and then reassess. And this lets me keep moving, even amid the panic.

If that sounds too simple, I thought so too at first. I learned this practice years ago from my therapist (for more on that story, read this earlier article), and over time, I realized that the experimenter’s mindset might be the most practical philosophy of change I’ve ever come across. It basically says, you don’t need to be certain—you just need to be open to learning.

and I discussed this in our podcast about clients who underspend—people who have the money to live a bit bigger but can’t quite give themselves permission. When choices are reframed as experiments, everything begins to feel more doable. And even fun. Instead of “You should spend more,” it becomes, “What if we tried this once, and talked about how it felt?” The experiment—time-bound, measurable, and debrief-able—helps loosen the grip of the status quo and provides insights.

We fail only when we can’t make that first move forward. Or, as the saying goes, “You miss every shot you don’t take.”

And here’s a really important the thing. Most of us don’t fail because we don’t know what to do. We fail because we don’t know how to fit what we want into the texture of real life. “How” isn’t a straight line; it’s a landscape. It’s terrain we have to walk, test, and revise. We have to experiment.

If we can be open to experimenting our way toward change—rather than committing prematurely to outcomes or untested plans, we might not only reach our goals more often, but actually enjoy the journey there, too.

And this isn’t just a mindset trick. Across psychology, coaching, and complexity science, the same pattern emerges: small, reversible experiments are what makes real transformation possible. Karl Weick (1995) calls them “small wins.” Dave Snowden (2020) calls them “safe-to-fail experiments.” Therapists use them as “behavioral experiments.” All describe the same thing: a way of learning that begins with curiosity, not certainty.

This is about learning our way forward; establishing a framework to experiment with money, meaning, and change. And what’s true for personal change is just as true in financial planning: progress starts with vision long before goals even come into the picture.

A Vision Is Not a Goal: Exploring the Story Beneath the Strategy

When I teach advisors about the psychology of change, I often start by asking them to imagine the first few minutes of a discovery meeting. The client sits down, maybe a little nervous, and the advisor begins with what feels natural:

“What are your financial goals?”

It’s a fair question—but also a really hard one, especially at the beginning.

Most people don’t walk into a financial planning meeting with a clear, emotionally grounded sense of what they want. Instead, they bring a handful of broad ideas: “retire at age 60,” “pay for college,” “travel more.” And my argument is that those are outcomes, not desires. They’re just goals. And many outcome-based goals are fragile. They shift, contradict, and often turn out to be means rather than ends.

What I’m getting at is this: vision and goals serve different purposes in both life and financial planning. And in many early conversations, the piece that tends to be missing is vision—a deeper picture of the life a person wants to live and the kind of self they’re becoming in the process. We have to have a positive, beautiful, fulfilling vision to be walking toward or we usually just stay with the status quo; we need a compelling reason to change.

This is where Intentional Change Theory comes in. Developed by Richard Boyatzis and his colleagues (2024), ICT shows that sustainable change doesn’t begin with problem solving (addressing the “real self”); it begins with visioning (imagining the “ideal self”). When people start by naming what excites and inspires them, they enter a psychological state called the Positive Emotional Attractor. It’s marked by openness, creativity, and intrinsic motivation.

The alternative—starting with deficits, fears, or immediate financial problems—activates the Negative Emotional Attractor, which narrows focus and triggers stress responses. You can’t dream big when your body is in fight-or-flight mode.

So before talking about what’s wrong and all the things that have to change, we have to talk about what’s possible and why that matters. That’s the essence of vision: it’s not a list of goals or a bigger goal. Instead, it’s a description of meaning. It’s the “why” behind the “what,” and it’s the “why” keeps us motivated and curious about the “how.”

In a discovery meeting, a vision-based opening might sound like this:

• “If you could design your ideal financial future, what would it look like?”

• “What does financial peace mean to you?”

• “When you think about the next decade, what would make you feel alive and proud?”

Vision comes first because it clarifies the emotional purpose of the journey. But even once a vision is clear, we still can’t leap straight to goals. Vision gives direction, but the path is always uncertain. And that’s where experiments come in.

An experiment is what translates a vision into lived experience. It’s how we test, refine, and adapt our way toward something that can’t be fully known in advance. And in this way, experiments help create a bridge between vision and goals.

Think of it as a progression in the following sequence (order of operation matters here):

• Vision gives direction—a sense of what matters and a foundation for the right strategy.

• Experiments encourage curiosity, creating movement before commitment.

• Goals provide structure. And when we first reflect on what we’ve learned through envisioning and experimentation, those goals become far more meaningful and motivating.

Because if you start with goals, you’ll just get compliance. But if you start with vision and move through experiments, you’ll get commitment… and much better data.

Suppose a client’s vision is to “live more freely” in retirement and to “spend more time on experiences, not things.” Instead of jumping straight into financial projections or bucket strategies, we can design a small experiment: take a two-week trip next year, spend at a level that feels slightly uncomfortable, and then come back to discuss what felt joyful, what felt wasteful, and what surprised them.

Now imagine that the client comes back and reports that, while they had a good time, the travel itself was exhausting. More importantly, the highlight wasn’t the destination at all—it was a cooking class they took along the way. Armed with this new data about what worked and what didn’t, the advisor suggests trying a few local cooking classes—no travel required. Over the next six months, the client discovers that taking classes with others embodies exactly what they meant by “living freely” and “spending on experiences.” With that insight, the advisor and client can now bake (pun intended!) a fully formed and meaningful goal into the plan: to have a “courses” bucket in the retirement spending plan that covers at least two classes a year, potentially with room to invite a grandchild, child, or friend to join.

When advisors invert that order—starting with goals or problems—they unintentionally move clients into a narrower, more evaluative mindset. And that shift can shut down the very curiosity that fuels sustainable change. Vision, experiments, and goals each rely on different emotional states and invite different kinds of questions to explore them effectively.

Before anyone calls this semantics, let me be clear: this isn’t about terminology. It’s about texture—the tone of the conversation and ideas that emerge from the mix of these three steps. When we ask about goals, we invite evaluation. When we propose an experiment, we invite participation. When we ask about vision, we invite imagination.

The table below outlines how these three elements differ in my mind and how they show up in real financial conversations. Advisors might use different words when exploring with clients, but the perspective that each element represents is what ultimately matters.

Vision gives energy and context. Experiments keep the vision alive and adaptive. And goals help build out the vision by giving it form. Without vision, plans lose meaning. And without experiments, goals lose their connection to the person they’re meant to serve. These emotional factors play an important role in keeping financial planning from becoming a process of technical optimization rather than personal transformation.

Experiments: The Bridge Between Vision and Goals

Once advisors encourage clients to explore their vision, the next step is experimentation: exploring how that vision actually feels in lived experience. If goal-setting assumes we already know ourselves, experimentation assumes we don’t—which, according to behavioral research, is far closer to the truth.

Karl Weick, one of the great organizational psychologists, once wrote that the key to progress is “small wins” (1995)—tiny, concrete steps that turn abstract problems into manageable actions. Importantly, Weick isn’t talking about SMART goals here. His small wins are small experiments: you try something, learn from it, and adjust. The learning compounds. You act your way into clarity rather than waiting for clarity to act.

Dave Snowden, whose Cynefin Framework helps leaders navigate complexity, uses a different term for the same idea: safe-to-fail experimentation. When cause and effect aren’t predictable—human behavior, markets, and emotions all interacting in shambolic ways—the best strategy isn’t to design one big, fail-safe plan. It’s to run multiple small tests and watch what happens. See what amplifies, what fizzles, and what emerges. Think of this as A/B testing—the iterative process used to understand what people actually respond to, rather than launching a marketing campaign and simply crossing your fingers, hoping it works.

Weick and Snowden may have been writing about organizations, but the same logic applies to people. Financial plans, careers, and relationships don’t unfold in straight lines. When life is complex, trying to plan your way through it is like trying to navigate a river from the shore. You can’t. You have to get in the water.

In therapy, this philosophy shows up everywhere. Cognitive behavioral therapists use behavioral experiments to help clients test beliefs rather than just talk about them. “If I ask for help, people will think I’m weak,” becomes an experiment: ask once and observe what actually happens. The point isn’t success or failure—it’s data. Acceptance and Commitment Therapy takes a similar approach: identify what matters most, take small, values-based actions, and adjust as you go. In both cases, change happens through experience, reflection, and adjustment, not through analyzing the problem in advance.

The same principle applies to financial decisions. Try a short-term spending or giving experiment this year, notice how it feels, and recalibrate. Instead of forcing a permanent identity shift—I’m a spender now—the client is simply gathering emotional data about what fits.

Importantly, experiments don’t require confidence. Confidence tends to grow through experimentation.

Anne-Laure Le Cunff (2025), founder of Ness Labs and author of Tiny Experiments, describes it beautifully: success isn’t a straight line from point A to point B—it’s a cycle of observation, hypothesis, testing, and reflection. Her framework invites people to turn vague intentions into small, intentional tests using her PACT model: Purposeful, Actionable, Continuous, Trackable.

• “I will write for fifteen minutes every morning for thirty days” instead of “I will finish my book this year.”

• “I will reach out to one new person each week for eight weeks” instead of “I will build a professional network.”

The distinction is simple but powerful: PACT focuses on outputs you can control, not outcomes you can’t. PACT’s reflection step—the trackable component—is the hinge. An experiment only matters if there’s a debrief. Without it, you’re just trying things. Learning happens in looking back—in naming what worked, what didn’t, and what it taught you about what matters.

In complexity science, this is called sensemaking: creating meaning from experience. In human terms, it’s how we grow. When we treat life as a series of safe-to-fail experiments, we stop demanding perfection from ourselves and start allowing presence. We stop expecting to know in advance what will work and start trusting that we can learn our way there.

That shift—from predicting to observing, from controlling to participating—isn’t just more accurate. It’s more alive.

Change doesn’t begin when we finally figure it all out. It begins the moment we’re willing to try something new and pay attention to what it teaches us. And when this experimental mindset is brought into financial conversations, it opens a whole new way for clients to explore their relationship with money.

Experiments With Money: Turning Vision Into Meaningful Goals

Money experiments don’t have to be grand or dramatic. They just have to be “enough” to feel something. An experiment is temporary, bounded, and meant to generate learning. That’s what makes it emotionally safe. The client isn’t committing to a new lifestyle—they’re trying something once, to see what it teaches them. The insights that come out of this work are emotional data. And these emotional insights become the raw material for meaningful goals, giving advisors clearer direction about what truly fits their clients’ values, identities, and lived experiences.

It’s not about right or wrong, smart or naive. It’s about noticing—how it felt, what it revealed, what it suggests for next time.

Experiments Lower the Stakes

One of the biggest fears among underspending clients is what one might call the slippery-slope worry. “If I fly business class once, will I get used to it? If I upgrade the kitchen, will that turn into constant remodeling?” This fear of losing control keeps people frozen in routines that no longer serve them. But an experiment interrupts that fear.

“Let’s try business class just for your next trip,” an advisor might say. “If you hate it, you never have to do it again.”

That one sentence—you never have to do it again—creates space for freedom, choice, curiosity, and agency. Clients can explore something new without the identity crisis of “becoming a spender.” They’re not changing who they are. They’re testing how something feels.

As my colleague Dr. Joy Lere often says, different doesn’t mean wrong. The more distance we can create between “this feels different” and “this must be wrong,” the more room there is for growth.

Experiments Generate Data, Not Judgments

Traditional financial plans tend to treat emotions as noise. Experiments treat them as data. After the test—the trip, the remodel, the gift—we debrief. What felt worth it? What didn’t? Was the discomfort about values, or just about doing something new?

Those reflections are the real outcome of an experiment. They tell us not just what worked, but why. A client might discover that the upgraded seats were worth every penny, but the five-star hotel felt hollow. Another might realize that generosity brings more satisfaction than indulgence. What can be learned?

Experiments Reconnect Present and Future Selves

Research from Hal Hershfield (2023) shows that people who feel more connected to their future selves tend to make wiser long-term choices. But most of us rarely feel that connection; our future selves can seem like strangers.

Experiments help close that gap.

When a client tries something they’ve been imagining—say, a trip or charitable gift—they get real-time feedback about whether that future vision actually fits. It’s the difference between planning for “someday” and learning from “today.”

That learning not only informs the financial plan—it reinforces the emotional bridge between who they are now and who they hope to be.

Experiments Build Identity Alignment

Many clients see themselves as “responsible savers.” It’s part of their moral and emotional DNA. They take pride in discipline, frugality, and prudence. Asking them to “spend more” can feel like asking them to betray themselves.

Experiments offer a different narrative: responsible people don’t blindly spend—they test, reflect, and adjust. Running a spending experiment isn’t reckless; it’s evidence-based stewardship. It honors both responsibility and curiosity. When clients see that, their identities expand. They can hold both saver and enjoyer, planner and participant.

Experiments Require Debrief

Debriefs can make the difference between novelty and growth, turning an event into information. It doesn’t have to be complicated—advisors (and individuals) can ask:

• What was most surprising?

• What felt worth it, and why?

• What could be done differently next time?

• Did this experiment reveal something new about values or habits?

Those conversations create a feedback loop that strengthens confidence. Each experiment becomes not just a one-off experience, but a data point in an ongoing sensemaking process. And the process compounds. When clients see that they can spend, learn, and still feel secure, they begin to trust themselves more deeply. That self-trust—not the experiment itself—is the real change.

Experiments Work Both Ways

While many of these examples focus on underspending, the same approach supports any behavioral shift: saving more, giving more, working less, or rebuilding a healthier relationship with money.

• Test an automatic transfer for three months and see how it feels.

• Curious about semi-retirement? Try a month off and notice what you miss.

• Want to give more to charity? Double a donation once and observe the emotional return.

Each is a safe-to-fail experiment—small enough not to break anything, meaningful enough to learn something. The goal isn’t to get it right; it’s to gather information that makes the next decision smarter.

A Process Advisors (and Individuals) Can Use

Because experiments are meant to generate emotional data, a little structure can offer cognitive clarity and make the experience more meaningful. A simple process can help clients understand what to try, how to engage with it, and how to make sense of what they learned.

1. Create: Identify a meaningful but bounded test. (“Try X for Y time.”)

2. Participate: Encourage full engagement. The goal is to feel the experience, not to hedge.

3. Debrief: Capture learnings soon after. Ask reflective questions.

4. Align: Decide what, if anything, to repeat or evolve into a new goal.

Over time, this process strengthens the client’s capacity to make sense of their financial choices and helps them develop a different kind of relationship with change—one with less anxiety, more participation, and deeper intention.

Why Experiments Create Real Change

Experiments shift money conversations from performance to participation. They move people from fear (“What if this goes wrong?”) to curiosity (“What might this teach me?”). And they remind both clients and advisors that money is not a moral test—it’s a learning tool.

When we treat financial behavior as a series of experiments, we restore something essential: the permission to learn in real time, by engaging with experience rather than relying on prediction. Clients gather emotional and experiential data that helps them understand what fits, what doesn’t, and why. And this work is what makes lasting change possible.

Experiments keep people engaged with their experience, create space for reflection, and build the self-trust needed to move from intention to action. And what clients learn from these experiments—what feels right, energizing, or aligned—builds a strong foundation for the goals they choose to pursue.

The Joy of Ongoing Discovery

By the time you read this, it will be January. A new year, a new start, a fresh list of goals. Some of us love the idea of beginnings—blank pages, vision boards, the neat boxes that outline what we plan to do differently this time. But the truth is, most resolutions collapse by spring. Not because we lack discipline or direction, but because goals alone can’t hold the weight of human change. Change is rarely about doing one big thing better. It’s about noticing what happens when we do something small in a different way.

Here’s one more consideration about vision, experimentation, and goals. Last month I wrote about psychological richness—a quality of life characterized not just by happiness or meaning, but by variety, complexity, and growth. It’s the feeling of being engaged in an ongoing experiment with living. A rich life, in that sense, is one that keeps teaching you something about yourself. Life should allow for false starts, surprises, and recalibration. We can welcome doubt, give ourselves permission to not know, and still have the courage to go find out.

Learning is a reward.

So greet this new year with permission to test, reflect, and adjust. You’ll begin to build a kind of confidence that no goal alone can give you. You’ll start to trust your ability to learn from whatever happens next. That’s the kind of self-trust that makes financial planning—and life planning—sustainable. It’s not about predicting the future. It’s about developing the resilience and curiosity to navigate it.

Because a life built on experiments isn’t aimless; it’s alive. It’s flexible enough to grow, forgiving enough to change, and grounded enough to hold whatever comes next.

Maybe this year, skip the resolutions. Skip the illusion that there’s a perfect plan waiting to be uncovered.

Instead, ask yourself:

What’s one experiment I could run this month to learn something about the life I want to build?

Start with a vision.
Run a small experiment.
Debrief what you learn.
Adjust as needed.
And then do it again.

The joy isn’t just in the arriving—it’s also in the discovering.

As always, a heartfelt thank you to my editor, . Thank you for helping stitch and smooth this one. Writing about how to experiment… is an experiment, and I am grateful to have you as a part of my debrief process.

References for the Nerds

Boyatzis, Richard E. 2024. The Science of Change: Discovering Sustained, Desired Change from Individuals to Organizations and Communities. Oxford University Press.

Hershfield, Hal. 2023. Your Future Self: How to Make Tomorrow Better Today. Piatkus Books.

Le Cunff, Anne-Laure. 2025. Tiny Experiments: How to Live Freely in a Goal-Obsessed World. Penguin Publishing.

Lere, Joy. https://joylere.substack.com/.

Snowden, Dave. 2020. Cynefin – Weaving Sense-Making into the Fabric of our World. Edited by Riva Greenberg and Boudewijn Bertsch. Contributions from Zhen Goh. Cognitive Edge—The Cynefin Co.

Weick, Karl E. 1995. Sensemaking in Organizations. Sage Publications, Inc.

At its heart, “holding space” isn’t about being mystical or passive. It’s about pausing before advising; resisting the urge to rush toward solutions. We want to let go of, at least for a bit, the compulsion to “right the ship.” Because, believe it or not, most clients don’t immediately need a fix; they first need to feel heard, understood, and safe.

We explain that “holding space” can sound like:“We’ll get to the strategy, but before that, I’d like to understand what’s going on more fully—would that be okay?” That small, structured pause brackets the conversation, gives clients permission to process, and signals that the advisor is confident enough to stay curious.

Ashley adds that clients are always—often unconsciously—asking one question: Are you there for me? Her favorite model, A-R-E, comes from emotionally focused therapy: be Accessible, Responsive, and Engaged. Responsiveness doesn’t mean leaping into action; it means attunement—acknowledging feelings, not just numbers.

Together we unpack the three H’s from Charles Duhigg’s Super Communicators: every conversation is really a request to be Heard, Hugged, or Helped. Advisors usually skip to “help.” But if you meet the first two needs—listening and emotional support—the technical advice that follows lands with far more trust.

We also touch on co-regulation—the science of calm being contagious. When advisors stay grounded and curious, clients mirror that steadiness. Like a 911 dispatcher who asks questions instead of panicking, curiosity lowers anxiety and keeps thinking flexible.

Finally, “witnessing” isn’t woo-woo; it’s a specific skill: reflecting, summarizing, and validating without rushing to reframe or sugar-coat. Sometimes it sounds as simple as, “That sounds really hard—thank you for sharing that.” Those micro-moments of empathy make advice more actionable and the relationship more durable.

Key Take-Aways

• Translate “woo-woo” into observable behaviors. Define what “holding space” looks like.

• Pause before advice. Curiosity beats correction.

• ARE you there for me? Accessible • Responsive • Engaged.

• Heard → Hugged → Helped. Don’t skip straight to the fix.

• Co-regulate. Your calm helps clients think clearly.

• Witness, don’t rescue. Reflect, validate, and resist toxic positivity.

• Woo-woo ≠ soft. These are hard, technical communication skills that make financial advice land.

Welcome to this month’s (Less) Lonely Meetings drop—a toolkit for turning each Less Lonely Money essay into meaningful, relationship-centered conversations.

Inside, you’ll find two ready-to-use tools:

• Client Companion – A reflection-first newsletter you can send to clients and prospects, normalizing creativity, learning, and connection as part of financial and emotional well-being.

• Meeting Ready Guide – A practical outline for bringing these ideas into your next 30-minute meeting—without scripts or jargon.

This month’s theme is about making—trying, experimenting, learning, and sharing.

Whether it’s cooking, painting, mentoring, or revisiting an old goal, “making” invites clients to experience something psychologists call psychological richness: the sense of living a life filled with variety, curiosity, and stories that change how we see ourselves and the world.

These conversations aren’t just uplifting—they deepen client relationships and bring meaning to financial planning itself.

Client Companion – This Month’s Client-Facing Newsletter

Newsletter Title: The Joy of Making: How Trying New Things Brings Us Closer

Best Used:

• When clients feel stuck or uninspired about next steps

• In January or midyear goal reviews

• With clients entering a new life stage or transition

• When couples are seeking shared experiences or purpose

Suggested Subject Lines:

• A New Way to Flourish This Year

• Why Trying Something New Might Be the Best Investment You Make

• The Surprising Link Between Creativity and Connection

Optional Intro Advisors Can Use:
Many of us begin each year with goals to improve or achieve. This month’s reflection invites a different kind of resolution: to make. To make something new, to make meaning, to make time for connection.

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The Joy of Making: How Trying New Things Brings Us Closer

When was the last time you tried something new—something you weren’t already good at?

Maybe it was cooking a new recipe, joining a class, or simply learning to fix something around the house. At first, it can feel awkward or even humbling. But soon, you notice something else: time slows down. Maybe you laugh more. You feel more alive.

Read more

Let’s start with tile.

I love tile. I always have. I take pictures of it everywhere I go—floors, walls, ceilings, balconies, even the under-side of balconies. Walking through old cathedrals or down narrow Spanish streets, tile both surprises and delights me. A pattern underfoot, a mosaic tucked beneath a balcony, a small act of beauty and thoughtfulness in a place you might have missed if you weren’t looking. I always think—I cannot help but think—someone cared. Someone used their hands to make something that still catches light and guides my path, centuries later.

This is what moves me about tile; the way it holds time. It’s the past, present, and future pressed together in clay and glaze. My husband’s grandmother has Mexican tiles in her home, and if you look closely, you’ll see tiny paw prints fossilized in the clay. These tiles were left outside to dry, and dogs and cats wandered across them. Imperfection made permanent, and so touching.

Now, living in Italy, tile is everywhere; it’s a Mediterranean staple. But more than simply being pretty—nicer to look at than asphalt or stucco—it’s a reminder of the history, artistry, and love. More to the point of this story, I told myself I wouldn’t leave Italy without learning to make tiles. And so I am. Or, I can now say, I have and continue to.

I found a teacher, joined a class, and learned how clay remembers pressure and touch, baking temperatures, molds, and ways to paint. I’m not good at it. My edges are uneven. My colors are off. But I love the process. There’s something about shaping something tangible and useful—something that might someday make a stranger feel what I feel when I see a mosaic in an old church: someone cared.

When I told friends I was learning to make tile, several said, “Oh, I took ceramics in high school!” I did not. I probably skipped that class for something I thought I was better at. I have often mixed together competence and identity. I thought being an artist was a type of person, and that person was not me. But it is.

Doing makes me an artist. Making gives me purpose. Whether I’m great at it or simply learning and loving it, it all count as artistry. Releasing myself from that old competence-versus-identity trap—refusing to get stuck in a duality I made up for myself—has broadened the person I am and what I bring into the world.

I can reflect on this now, hopefully somewhat succinctly, only because it’s a familiar pattern, and really a practice, in my life. The practice of engaging in things before feeling “ready”: research before I became a PhD, cooking before I could do much more than boil water, language-learning before I became conversationally fluent, writing before I ever became (and still struggle with being) a good writer. I do not need to be “good” to begin.

And neither do you.

So I can’t help but wonder: what would happen if we all treated 2026 as a year of making? Not for mastery or recognition, but for the joy of trying—together.

Why Making Matters

Before tile, there was cooking.

When my husband and I first met, he wooed me with food. He could cook anything—and everything he made was the best version of it I’d ever eaten. I, on the other hand, could boil eggs (sometimes correctly…who can ever remember whether you’re supposed to wait for the water to boil before adding the eggs—or is that pasta?). That was it.

Then he got stationed on Diego Garcia, an island in the Indian Ocean, for a year. My meal ticket walked out the door, and there was only so much yoga I could do. So, I decided to learn to cook. I wasn’t a chef; I was a woman armed with the New York Times Cooking app and misplaced confidence.

My roommate, Jack, became my first—and often only—taste tester. Inspired by Nora Ephron’s 2009 movie, Julie & Julia, where a woman cooks every recipe from Julia Child’s cookbook, I set out to make whatever recipe of the day appeared on the NYT app, no matter how absurd it sounded. One day it was lentil stew; the next, baked fish I didn’t know how to debone.

It wasn’t pretty. There was smoke. There was confusion. There was, on more than one occasion, undercooked chicken. But there was also laughter. Jack and I would stand in the kitchen and guess whether dinner was safe to eat, or whether we’d be ordering pizza.

And in that daily ritual of trial and error, I learned more than how to cook. I learned that making something, even badly, builds connection. We’d sit down with our mismatched plates and talk about our days, our futures, and the absurdity of adulthood. Sometimes my brother and other friends who also lived in the building would stop by. They knew I was learning to cook and tried to be supportive… they were also law students who were hungry for anything resembling a home-cooked meal.

Cooking turned my empty evenings into a rhythm. It gave me a way to show care, to participate, to belong. By the time my husband returned, I could feed us both. He now swears I’m the better cook. But what I really gained that year wasn’t a skill; it was a sense of agency and community. Each burned or bitter meal still made memories and emboldened my spirit for the day ahead.

That’s the thing about making: it’s never just about the thing itself. The act of creating—even something ordinary—fills our lives with what psychologists Shigehiro Oishi and Erin Westgate (2025) call psychological richness. Most of us have been taught that a good life is either happy (hedonic) or meaningful (eudaimonic). But recent research suggests there’s a third dimension, a rich life, defined not by comfort or purpose, but by variety, curiosity, and perspective-changing experiences.

In a 2025 study, Naoki Konishi and colleagues found that people who live psychologically rich lives report more confidence and adaptability—but also more fatigue and even loneliness. Richness, it turns out, isn’t restful. But it remains vital. It stretches us. It exposes us to friction and feeling, to the very things that make us come alive.

Cooking was exactly that for me: a daily mix of joy, frustration, creativity, and humility. Each mistake was a small experiment in resilience; each success a reminder that we grow by doing, not by knowing. The research echoes what those messy meals taught me: richness is a trade-off. You gain perspective, but you also get tired. You build confidence, but only by facing failure. You connect, but sometimes only after embarrassment. The reward is not stability—it’s depth.

A psychologically rich life might not always feel good, but it feels alive. It’s the life that gives you stories to tell—the kind that makes you say, “You won’t believe what happened when….” That’s what making offers us: a way to keep learning who we are through what we do. Not in grand gestures, but in small acts of care and curiosity: cooking dinner, learning a phrase in another language, tile making, writing.

The richness isn’t in the result—it’s in the reach itself.

There Are No Creative Imposters

Creativity often gets romanticized—as if it’s a spark, a gift, or something bestowed by the gods upon a select few. But as reminded his readers in a recent blog post, creativity is less magic and more muscle. It’s something we can build.

Duhigg distills decades of research on the creative process into three simple ingredients: novelty, deliberate rest, and ritual. Creativity thrives when we expose ourselves to something new—new people, new places, new ways of thinking. It also flourishes when we step away, when we let the brain wander and connect ideas beneath the surface. And, maybe most surprisingly, it depends on small rituals—tiny habits that prime the mind to make.

Stress, of course, can crush creativity. But the right kind of challenge—a playful one—can rekindle it. Duhigg calls this creative desperation: when you give yourself just enough constraint (“I’ll write for ten minutes” or “I’ll make a single mold for my tile today”) to remove the pressure to be brilliant. Paradoxically, limits make us freer.

I keep a folder in my phone called “Random Notes.” It’s full of unfinished sentences, half-thoughts, and random quotes I want to remember. I jot things down waiting in coffee lines, between classes, while cooking dinner. Sometimes I don’t even know why I wrote something—it just felt like a thread I might follow later.

Tile has its own rituals, too—measured, messy, and meditative. Mixing glaze. Pressing clay. Waiting for it to dry. Learning how to forgive the cracks. You can’t rush a kiln any more than you can rush clarity. Both demand patience and a kind of faith: that something will emerge if you keep showing up.

Making, in any form, is its own small experiment in trust.

Both tile and writing remind me that play is the antidote to perfectionism—it is also that third leg of flourishing: psychological richness. When I treat the process as serious work, I freeze. When I treat it as a game—when I say let’s see what happens if…—I relax.

When I started writing in January 2025, in my own voice, I felt like an impostor (weird, I know). After years of academic and technical writing, it was strange to sound like myself—and also strange to imagine that sounding like myself might actually be something someone else would enjoy or care about. Being me was really hard.

Then, in March, when I was doubting myself, I read something from organizational psychologist that changed how I thought about sharing ideas. He reframed self-promotion as idea promotion—sharing ideas as an act of generosity rather than ego.

“The focus,” Grant said, “is on the gift, not the giver.”

Sharing isn’t about saying look at me; it’s about saying here’s something I made that might be valuable to you. Its back to my obsession with tile. I could let go of ego because I believed that even if people didn’t like it, they would still see that I really cared.

Grant also described sharing as a form of self-expression and social contribution. He pointed out that when we hold our ideas back, we deny others the chance to benefit from them. That hit me. I realized my hesitancy to share wasn’t humility, it was fear disguised as modesty. And I didn’t want fear to hold me back from showing that I care.

He said something else that stuck with me: “If you doubt yourself, shouldn’t you also doubt your judgment of yourself?”

Impostor syndrome, he argued, is a paradox of judgment. When other people believe in us, maybe that’s a sign we should start believing them, too (Thank you to , my editor, who has always believed in me from the very beginning). That shift—from self-protection to generosity—made me braver.

So, I’ve kept writing. This article marks twelve months. And I can tell you that I’ve published drafts that weren’t perfect (not because of Erica’s editing, but because months later I’d reread my work and think, that could have been better). But what matters more is that by sharing these imperfect drafts, I’ve allowed people to see evolving, incomplete thoughts—and through all of that, something special has happened: people responded.

My words have helped people feel something, think differently, or simply remember they aren’t alone in their own messy process of trying to be human. There’s someone else out there, and they care. It’s no different from cooking and feeding my friends—they didn’t care that there was too much salt. It still filled their tummies, and there was a lot of laughter along the way.

(Less) Lonely Money isn’t just a newsletter about psychology or planning. It’s a practice—a way of building connection through ideas, imperfection, and the act of making something, caring about something, and sharing it.

Duhigg also notes that sharing is a crucial, and often overlooked, part of creativity. Artists who reveal their work earlier—before it’s polished—report more confidence and lower fear of failure. Sharing turns creation into conversation.

Creativity, in other words, is relational. It begins alone but comes alive in connection.

That’s what makes it so powerful—and so healing. Every time we create, share, and respond, we participate in the quiet, everyday art of making life a little less lonely and a little more rich.

Everything Is Better Together

At this point, I have a feeling some of you are with me: I’m advocating for everyone to make 2026 a year of making. And while I’ve made the case that sharing this process with others is a good idea, it turns out—it isn’t just an idea. It’s science. Doing together is always better than doing alone.

Earlier this year, psychologists Dunigan Folk and Elizabeth Dunn asked a simple question: Are some activities just better alone?

Using more than 100,000 daily activity reports from over 40,000 people in the American Time Use Survey, they analyzed how happiness varied across 80 different everyday tasks—from eating and commuting to cleaning and reading.

The result was remarkable: every single activity—yes, all of them—was rated as more enjoyable when done with someone else. Of the 297 activity-specific coefficients they examined, only one was negative: cleaning the kitchen in 2021. (And honestly, if ever there was a year to prefer solitude while scrubbing dishes, that was probably it.)

Even traditionally solitary activities—like reading, exercising, or running errands—became more enjoyable when shared. “Happiness thrives in the company of others,” they wrote, a finding so universal that it’s hard to overstate. Whether we’re eating, walking, or simply existing, everything is better together.

I see that truth everywhere in my own life. And you already know the stories of cooking, tile making, and writing, so here’s another.

When learning a new language, mistakes are only funny because someone else hears them. Once, for example, I called a man a rabbit (conejo) instead of a jerk (cabrón). It wasn’t just language failure—it became a story my friend shares time and time again, and we laugh harder every time. Another time, I told the movers to “put my bones in the corner of the room.” I meant furniture (muebles, not huesos). And I will never forget the look on their faces.

When Folk and Dunn found that people were happier across every activity when accompanied, they weren’t measuring productivity or meaning—they were measuring aliveness. Connection doesn’t necessarily make us more efficient, but it does make us more human. It turns the routine into ritual.

The data also suggest something deeper: that we systematically underestimate how much happiness connection will bring. We assume solitude will be restful or easier, but the evidence shows that almost everything is more enjoyable—even the mundane—when someone else is there.

That realization has reshaped how I think about flourishing. It’s not something we build alone. It’s something we build between us.

Happiness thrives in company.

Meaning deepens in conversation.

Even solitude—reading one’s own book in a room of others reading—softens in someone else’s presence.

The Courage to Share

Learning anything new is equal parts curiosity and humiliation.

When I first created (Less) Lonely Money, I’d hover over the “post” button for ten minutes before clicking. Each essay felt like a dare—not because I thought people would dislike it, but because they might not care. Silence, more than criticism, was my biggest fear.

And then there’s language. My linguistic chaos has continued in Italian—I’ve mastered “Hugo Spritz, grazie,” and not much else—but I can tell you I have the best time out in town speaking broken Italian, Spanish, and English to anyone who will listen and practice with me because they find it endearing as well.

Cooking was the same. My early meals were disasters dressed as dinner, but they became a ritual for my roommate Jack and me. Cooking became more joyful when I stopped worrying about whether the dish was good and focused instead on feeding the people I cared about.

Generosity is a surprisingly sturdy form of confidence. It doesn’t deny fear; it just gives fear a job to do. You stop asking, “Is this good enough?” and start asking, “Could this be useful to someone else?”

That’s what makes sharing courageous. Not because it proves expertise, but because it invites company. Every honest word, every imperfect tile, every conversation about something we’re still learning is a rebellion against loneliness.

Courage, in the end, isn’t the absence of doubt. It’s the decision to face the doubt… and keep making—and keep sharing—anyway.

Questions for a Less Lonely 2026: Flourishing Through Participation

By now I’ve learned that flourishing has less to do with balance and more to do with participation. Flourishing isn’t a tidy blend of happiness and purpose. It’s the willingness to be in process with other people—to let curiosity replace certainty, to trade mastery for participation.

When we participate, we stop measuring our lives by outcomes and start noticing the relationships that form around what we try. A cracked tile, a burnt dinner, a misspoken word—all of them become artifacts of connection. They’re reminders that we were here, that we reached toward something, and that someone reached back.

You don’t have to take a pottery class or start a Substack to step into 2026 differently. You just have to turn what you’re already doing into a shared experiment—with yourself, a friend, a partner, a client, or a colleague. So here are a few questions help us do that.

For Advisors and Colleagues

To bring psychological richness and creativity into client or team conversations:

• What’s something you’ve never tried—financially, creatively, or personally—but might enjoy experimenting with this year?

• When was the last time you learned something new that had nothing to do with work or money? What did it teach you about how you learn?

• Who helps you see things differently—and how might you include them in your next big decision?

• What project or plan could you share before it’s perfect, just to invite feedback or laughter?

• How could you make your next client review, family meeting, or team retreat feel more like making something together than ticking through a list?

For Individuals, Couples, and Friends

To weave connection and curiosity into everyday life:

• What’s one small, slightly ridiculous thing you’d like to learn or make in 2026?

• Who could you invite to learn it with you—or simply to cheer you on while you try?

• When was the last time you laughed at your own beginner-ness? What made that moment feel light instead of heavy?

• Which part of your life feels too polished, too finished—and what might open up if you let it be a work-in-progress again?

• How can you remind yourself that sharing, not mastery, is the point?

For Everyone

A meta-reflection on richness and connection:

• Where in your life do you want more variety rather than more certainty?

• What might flourishing look like if it meant feeling engaged instead of comfortable?

• Who could you make something with this year—a plan, a story, a meal, a memory?

These aren’t planning questions so much as permission slips—to make, to share, to be seen. Each one turns a solitary act into a social one, a task into a chance for connection.

Closing Reflection

I want to circle back to a point that many of you might have read over but not let sink in: psychological richness can—and often does—feel a little lonely. By definition, it stretches us beyond the familiar. We grow through friction—by trying, failing, laughing, and trying again. But growth without witness can become isolation, and curiosity without company can start to feel like mania (I promise you).

The big idea, then, is to let richness and relationship complete one another: to bring our experiments into shared space, to let others see our process instead of our polish.

A few months ago, I wrote about a note I keep in my phone that says, “Forego the quest for certainty”. Well. I have another one, and it says, “Before you can be anything, you have to be a beginner.”

So as 2026 approaches, I implore you—be willing to be a beginner. Find a friend who doesn’t know what they’re doing either, and commit to laughing as you learn.

Psychological richness gives us texture; friendship gives us warmth. One teaches us how to live; the other reminds us why.

So here’s to a year of making things—and making meaning—together.

My sincerest gratitude and appreciation for . None of this would be possible or as readable without you. Onto the making in 2026!

Research for the Nerds

Duhigg, Charles. “The Science Behind Creativity.” The Science of Better (blog). 2025. October 4. https://charlesduhigg.substack.com/p/the-science-behind-creativity.

Ephron, Nora, dir. Julie & Julia. Columbia Pictures, 2009.

Folk, Dunigan and Elizabeth Dunn. 2025. “Everything Is Better Together: Analyzing the Relationship Between Socializing and Happiness in the American Time Use Survey.” Social Psychological and Personality Science. 0 (0): https://doi.org/10.1177/19485506251364333.

Grant, Adam. 2025. LinkedIn. April. https://www.linkedin.com/posts/adammgrant_have-you-ever-hesitated-to-share-your-work-activity-7311774949793234944-9rme.

Konishi, Naoki, Motohiro Kimura, Ken Kihara, et al. 2025. “Psychological Richness as a Distinct Dimension of Well-Being: Links to Mental, Social, and Physical Health.” PLoS One. June 18. 20 (6): e0326528. https://doi.org/10.1371/journal.pone.0326528.

Oishi, Shigehiro and Erin C. Westgate. 2025. “Psychological Richness Offers a Third Path to a Good Life.” Trends in Cognitive Sciences. ISSN 1364-6613: https://doi.org/10.1016/j.tics.2025.04.002.

In this conversation, and I argue that the absence of explicit expectations creates unnecessary anxiety and broken trust. Clients regularly apologize for calling (“I know you’re busy”), hide decisions (“We already bought the house”), or misunderstand what services are available (“I thought you only managed investments”). These behaviors aren’t signs of disengagement—they’re signs of confusion.

I explain that clients have mental templates for most service relationships: they know what to expect from a doctor, lawyer, or car salesperson. But few have a model for financial planning. Without structure, uncertainty grows. Advisors can pre-empt that tension by starting relationships with an expectations meeting—a structured conversation about how the relationship works, when to communicate, and what success looks like.

Ashley connects this to therapy’s informed consent process, which clarifies logistics, financial obligations, and relational boundaries before the first session begins. Advisors can borrow that structure to create an “expectations document” that covers:

1. Principles and philosophy – Why you do this work and how you approach planning.

2. What clients can expect from you – Preparedness, communication cadence, cancellation policy.

3. What you expect from clients – Honesty, engagement, timeliness.

The key is not paperwork alone but conversation. Setting expectations verbally (and revisiting them regularly) creates safety, predictability, and trust. It also protects advisors—especially when working with couples or multiple generations—by clarifying confidentiality and boundaries. For example, couples can be informed of a “no-secrets policy,” while families can understand how shared financial information is handled across generations.

We emphasize that expectations aren’t about restriction—they’re about relief. Clients relax when they sense the advisor has a framework. It signals competence and care. Even a simple, branded one-page document conveys intentionality and professionalism.

Finally, our conversation turns to curiosity: the best expectations meetings are two-way. Advisors should ask clients, “When do you want me to call? What does success look like? When do you want to hear from me—and when not?” These questions transform onboarding from a transaction into a collaboration.

Key Take-Aways

• Clients don’t know the “rules” of financial planning—teach them.

• Begin relationships with a clear expectations meeting.

• Borrow from therapy’s informed-consent model: clarify principles, logistics, and boundaries.

• Put it in writing—brevity and branding make it feel official and thoughtful.

• Review expectations annually or during life transitions.

• Address couples and multigenerational dynamics upfront.

• Ask curiosity-based questions about how clients define success and support.

• Clarity isn’t limiting—it’s calming. It builds trust, reduces anxiety, and makes advice easier to follow.

If you enjoyed this talk and want more on this topic, go check out the webinar we just did by clicking here. And consider following both Ashley and I on LinkedIn to keep up with free quarterly webinars on topics just like this one!

Welcome to this month’s drop from (Less) Lonely Meetings—a toolkit for turning each Less Lonely Money article into real, relationship-centered conversations.

Inside, you’ll find two ready-to-use tools:

• Client Companion – A reflection-first newsletter you can send to clients and prospects, normalizing the role of regret in a good life.

• Meeting Ready Guide – A practical outline for bringing these conversations into your next 30-minute meeting—without scripts or therapy talk.

This month, we explore regret—not as failure or weakness, but as proof of care and agency.

Your clients, particularly high-achieving and high-net-worth individuals, are rarely strangers to success. Yet the same freedom that brings flourishing also expands opportunity—and therefore, regret. They may have more choices, but also more counterfactuals, more “what ifs.”

Advisors who can name regret and meet it with empathy help clients integrate, not avoid, their emotional realities. These conversations don’t just relieve pressure—they build trust, clarity, and self-understanding.

Client Companion – This Month’s Client-Facing Newsletter

Newsletter Title: When Success Hurts: Why Regret Is Proof You Care

Best Used:

• After major financial decisions or liquidity events

• During retirement transitions or business exits

• With clients feeling restless or second-guessing big choices

• In annual reviews where emotions run deeper than numbers

Suggested Subject Lines:

• The Hidden Emotion of Success

• Regret Isn’t Failure—It’s Feedback

• How to Talk About “What Might Have Been”

Optional Intro Advisors Can Use:
We all experience regret—even when things are going well. This month’s reflection looks at how regret and flourishing often travel together, and why naming regret out loud can turn it from self-blame into self-knowledge.

Full Text (Copy/Paste into Email)

When Success Hurts: Why Regret Is Proof You Care

We don’t usually associate regret with living the “good life.”

If anything, we imagine regret as the opposite of flourishing—a signal that something has gone wrong. But in truth, regret is often a sign that we’re paying attention. It’s the cost of caring.

Every time we make a choice that matters—whether it’s career, family, or lifestyle—we also close the door on another possible life. Sometimes, we notice that closed door. We wonder what might have been. We think, painfully, If only I had…

That’s regret. But it’s also reflection.

And for people who’ve worked hard to build meaningful, successful lives, regret is surprisingly common.

Why Regret Is So Common Among High Achievers

Psychologists Neal Roese and Amy Summerville describe regret as a counterfactual emotion—one that relies on imagining how life might have turned out if we’d chosen differently.

It’s not just sadness or disappointment. It’s a mental time-travel that compares reality to the road not taken.

And here’s the paradox: the more options we have, the more regret we’re likely to feel.

That’s not pessimism—it’s math.

When you’ve achieved enough to have choices—financial freedom, career mobility, the ability to say yes or no to opportunities—you also create more possible versions of your life to compare against.

You may not consciously think of it that way, but your brain keeps a running tally of “what ifs”:

• If I’d taken that role, would I feel more fulfilled?

• If we hadn’t sold the business, would I be happier—or more stressed?

• If we’d stayed closer to home, would life feel simpler?

You can love your current life and still feel that tug. That’s not discontent—it’s depth. It means you’re living a life full enough to contain both gratitude and wonder, pride and ache.

Read more

Kevin, however, didn’t offer sympathy or platitudes, and he wasn’t commiserating with Carl the same way I had been. Instead, he asked Carl an incisive, unsettling question: “Do you ever think about how morally culpable you are for being in charge of your own schedule?”

Mic drop.

As Carl explains (and I agree), Kevin’s question was one way of implying that the more freedom we have, the more responsible we are for our choices. And with every choice comes the possibility of regret.

This hit me hard. Regret has been an ever-present emotion in my own life lately. With each step, each decision, I’m reminded that saying yes to one path quietly says no to others, closing the door on potentially exciting opportunities. This isn’t FOMO—that social-media-fueled excitement or anxiety about what others are doing. What I feel is weight. Pressure. It usually comes from my own daydreams of what could have been.

For instance, take work. I’ve made several career changes in the past few years and sometimes wonder if any of them were the right choices. If I had chosen differently, would I have made more money? Built more security? Felt less guilty about wanting a little more email-free vacation? Entertaining regret has helped me to recognize that, maybe more than money or stability, creative freedom is my north star (though an email-free vacation still sounds good). I can’t imagine being unable to write what I want, to teach in my own way, or chase projects that don’t always make balance-sheet sense but that matter deeply to me—even if that means forsaking a steadier paycheck. The moral of the story: even when we’re content, every path still carries its own regret.

The same tension shows up in parenthood and marriage, exactly what Carl Richards and Kevin Dahlstrom were discussing. Every hour poured into work on a Saturday or late into the evening is an hour not spent with family. And every hour with family is an hour we don’t pour into work (which, for me, is work I often really enjoy). There’s no way to choose without some measure of loss.

Here’s another example. I’ve worked hard to live abroad; I’m currently in Italy. Travel shapes me in profound ways that I’m proud of and wouldn’t want to change. I know my heart-home is in Spain, but I still feel the pull of another life—the version of me who stayed close to “home-home,” the place where my kids could see their grandparents more regularly and I could see my friends. I often juxtapose my “wild” life abroad with a steadier one with family and friends.

Here’s the paradox: flourishing—living a life I very much love—doesn’t erase regret. Instead, it can multiply it. Because as flourishing opens doors, it also imposes agency. And agency—being able to choose one path over multiple possibilities—will sometimes mean regret.

Carl came to a similar conclusion on the podcast, stating that “part of flourishing is regret.” Not as punishment for living well, and not as a complaint about success. What I think he was suggesting is that regret is often the counterbalance, the cost, of the freedom to choose. If we care about our choices and we’re honest about their consequences, we will sometimes feel regret even when we are living our best lives.

So I want to reframe regret. It isn’t proof that we’re failing or choosing poorly. Instead, maybe experiencing regret is evidence that we’re engaged with life, recognizing the opportunities available to us, and trying really hard to be thoughtful about making the best choices. And, unsurprisingly, it’s something we need to be able to talk about—openly, calmly, thoughtfully, compassionately, and bravely—much like Carl and Kevin did.

That realization—that regret is so closely related to agency—has shifted something in me as I’ve researched this article. I used to think regret was something to manage, minimize, or banish altogether. Now, at least sometimes, I’m trying to see it differently. Like all emotions, regret isn’t good or bad; it’s information. Even when it’s messy—wrapped in sadness or grief, arriving alongside pride, joy, or love.

To flourish doesn’t mean to live regret-free. It can mean living with regret as a companion for reflection, a teacher. Which raises the question I want to explore: if flourishing and regret are intertwined, what does that mean for how we think about emotion, decision-making, and the stories we tell about having a “good life”?

What Regret Really Is (and Why It Matters)

At first glance, regret seems easy to classify. It feels bad. It looks backward. It carries that sting of if only I had chosen differently. For decades, psychologists framed regret as a negative emotion with mostly destructive consequences: rumination, lower life satisfaction, even depression (Lecci et al. 1994; Schwartz 2000).

But that picture is incomplete. More recent research suggests regret is far more interesting—and far more valuable—than we once believed.

Regret as a Counterfactual Emotion

Psychologists Neal Roese and Amy Summerville (2005) describe regret as a “counterfactual” emotion—unlike sadness or anger, it relies on imagining what might have happened if we’d chosen differently. Regret isn’t just about what happened; it’s about mentally time-traveling or maybe even alternative-world-traveling, through the roads not taken: If only I had…, If only I went…, If only I knew…

That counterfactual quality is what makes regret sting, but it’s also what makes it useful. Regret links past and future, transforming “mistakes” into information. When I regret not preparing more fully for something, it pushes me to prepare better next time. When I regret speaking too sharply, it reminds me to pause before responding the next time I’m tired or frustrated.

In this sense, regret isn’t simply about loss or loathing; it’s about learning.

Roese and Summerville (2005) conducted a meta-analysis to explore the most common regrets and, across thousands of participants, the results were remarkably consistent across six domains:

1. Education—not staying in school, not studying harder, not earning a degree.

2. Career—missed opportunities for advancement, choosing the wrong path.

3. Romance—relationships not pursued or not sustained.

4. Parenting—not spending enough time with children, parenting mistakes.

5. Self—failing to improve one’s habits, attitudes, or personal growth.

6. Leisure—not traveling, not enjoying life when the chance was there.

What unites these categories is opportunity. They all involve areas of life where choice and change remain possible. Education can continue at any stage. Careers can change course. Relationships can begin, end, or heal. Parenting and self-development offer daily chances to recalibrate. And leisure can always be reclaimed.

By contrast, regrets tied to things we can’t change—like a terminal illness or an unavoidable accident—tend to fade more quickly. When change is impossible, cognitive dissonance steps in, helping our minds stop re-thinking the situation and allowing us to make peace. But when change is possible, regret lingers.

People Value Regret More Than Other Negative Emotions

One of the most striking findings in the literature comes from Colleen Saffrey, Amy Summerville, and Neal Roese (2008). They conducted a study where participants were asked to rate twelve negative emotions and found that regret ranked highest—not just as tolerable, but as useful.

Participants reported that regret was the most beneficial negative emotion across five important functions:

1. Making sense of the past—placing events in context.

2. Refining approach behaviors—motivating us to pursue better outcomes next time.

3. Developing avoidance behaviors—helping us steer clear of mistakes.

4. Gaining self-insight—deepening our understanding of our values and tendencies.

5. Fostering social harmony—strengthening relationships when expressed skillfully.

In short, people don’t merely endure regret they can and often do value it. Unlike fear, anger, guilt, or disappointment, regret is both painful and instructive. Even though it’s an emotion that many identify as “negative,” it’s one that people willingly keep around.

Regret’s Double-Edged Nature

Of course, regret has its costs. Too much dwelling on “what might have been” can spiral into rumination, pulling us away from the present moment. It can also bias future decisions, leading us to avoid healthy risks (Connolly and Zeelenberg 2002).

But that doesn’t make regret inherently bad. It just means it requires interpretation. Regret signals something feels misaligned between our values and our choices, but it doesn’t always tell us what to do about it. As says, emotions are informational, not instructional. The challenge is to listen carefully to gather all of the relevant information without letting the signal consume us too quickly or making us immediately react based on an incomplete lesson plan.

That distinction helps explain why people’s beliefs about regret often differ from how it feels. In the moment, regret hurts. But with time, many come to see it as beneficial—a painful teacher whose lessons are worth the discomfort.

How Flourishing Complicates Regret

So rather than asking whether regret is good or bad, perhaps the better question might be: What can regret teach us?

When I look back on choices in my career or my parenting, I don’t want to erase regret. It’s often the very thing that sharpens my awareness of what matters most. Regret points toward my values, shows where I’ve drifted, and sometimes reveals the impossible trade-offs that flourishing requires. It reminds me that there was never a perfect path, only a human one.

The cultural script of “no regrets” misses this truth entirely. To live with no regrets would mean either having no real choices or refusing to care about their consequences. Neither sounds much like flourishing to me.

Arrival Fallacy

Let’s toss another psychological phenomenon into the mix: arrival fallacy.

Arrival fallacy is the mistaken belief that reaching a long-sought goal will deliver lasting happiness. But the reality is more complicated.

Scottie Scheffler, the current top-ranked golfer in the world, recently described this with striking honesty, and then wrote about it on his Substack. When asked how long he celebrates a victory, he admitted that the euphoric high of winning lasts only “a few minutes.” Then, almost immediately, he’s left wondering what’s next; questioning the deeper purpose behind the pursuit. “You win, you celebrate, you hug your family… and then it’s like, okay, now what?”

Scheffler acknowledged what many achievers eventually discover: professional accomplishments bring pride and gratitude, but they rarely touch “the deepest places of your heart.” For him, fulfillment comes more from being a husband and father than from holding trophies.

His reflection mirrors the arrival fallacy perfectly. Achievements don’t banish regret; they can amplify it. The very act of achieving reveals new trade-offs, reminding us that flourishing and regret are not opposites but companions. You climb the mountain, win the tournament, publish the book, and then realize you are still yourself—still faced with trade-offs, still aware of choices made and not made.

Opportunity Breeds Regret

If regret is the emotion of “what might have been,” then it follows a simple rule: the more possibilities you have, the more regret you can or may feel.

Neal Roese and Amy Summerville (2005), and later Denise Beike, Keith Markman, and Figen Karadogan (2009), call this the lost opportunity principle. They argue that regret tends to be most intense in life domains rich with opportunity. In other words, regret lives and lurks in places of prosperity.

This is why flourishing and regret are so often linked. Flourishing expands opportunities: more freedom, more choices, more resources, more paths to pursue. But every new choice brings with it an equal and opposite shadow: the recognition that another choice will go untaken. It’s not uncommon to feel great (pride, accomplishment, happiness) and not great at the same time (regret, confusion).

Advisors may recognize this paradox in planning moments—retirement, equity windfalls, relocation—where flourishing expands choices and, with them, the counterfactuals clients must lovingly set down.

The Impurity of Emotion—Why Regret Feels So Strange in Good Times

If regret were only pain, it would be easier to dismiss. We would feel it, recoil, and move on. But regret is rarely that clean. It often shows up, as discussed, at the very moments when life looks good. And that’s what makes it so unsettling.

Travis Bradberry, coauthor of Emotional Intelligence 2.0, recently wrote a thoughtful post on LinkedIn about emotions and their common “impurities.” Many complex emotions are blends of other feelings that together create the rich, sometimes confusing texture of our inner life. Joy plus sadness becomes bittersweet. Confidence plus vulnerability becomes courage. Even anger, when mixed with hope, can become determination.

Regret is no exception.

Regret Plus Pride, Maybe Disillusioned or Skeptical

Think about finishing a big project at work or reaching your retirement goals. There’s the satisfaction of completing something difficult. But often there’s also a pang: I should have started earlier. I could have done better. Pride and regret walk side by side. One doesn’t cancel the other.

Scheffler’s reflections are a vivid example. Pride at reaching world number one sits directly beside the emptiness of asking, “What’s the point?” The arrival fallacy is, in many ways, pride plus regret: the high of achievement paired with the pang of realizing it didn’t transform life as expected. Together, they create a fuller picture of what mattered in that experience and what might be done differently next time.

Regret Plus Gratitude, Maybe Reverence or Inquisitiveness

The same thing can happen with gratitude. I often feel deeply grateful for the choices I’ve made in my career. I love the creative freedom, teaching, the chance to work on projects that align with my values. And yet, alongside that gratitude is a flicker of regret: Would life have been easier if I’d chosen the corporate path? Would I feel less financial strain?

Gratitude doesn’t erase regret. Regret doesn’t erase gratitude. Instead, they coexist, complicating one another, making us tease apart, question, and turn over what’s most important in our minds.

Regret Plus Ambition, Maybe Restlessness or Critical

Ambition is another frequent partner of regret. You might be flourishing in your field, accomplishing things you once only dreamed of. And still, regret can creep in: Why didn’t I take that bigger risk? What did I give up to pursue this with such fervor?

The presence of regret doesn’t undermine ambition; it refines it. Regret shows where growth still calls and where possibility still pulls.

Why Blends Matter

Bradberry’s point is simple but profound: emotions are not neat categories. They are signals, often overlapping, informing and shaping one another. To expect regret to be pure is to misunderstand how human feelings work.

And yet, that misunderstanding is common. Again, we’re taught to divide emotions into “good” or “bad.” Joy and gratitude belong on one side of the ledger; regret and anger on the other. But emotions are not moral judgments. They’re information. They show us where we stand in relation to our values, our relationships, and our goals.

This “informational” not “judgmental” perspective changes how we interpret regret in flourishing contexts. Too often, people assume that regret contaminates success: if you feel regret after an accomplishment, something must be wrong. If you feel regret during a season of gratitude, you must be ungrateful.

But impurity isn’t always contamination—sometimes it’s texture. Just as a piece of music is enriched by harmony, not diminished by it, our emotional lives are enriched by blends. Flourishing isn’t about experiencing only joy or only pride. It’s about holding the complexity:

• Regret blended with pride signals that we care about doing things well.

• Regret blended with gratitude signals that we can see both what we have and what we’ve left behind.

• Regret blended with ambition signals that we’re still striving.

If we take Bradberry and Lere seriously, the lesson is not to fight the impurity of emotions but to learn from the texture it creates. Instead of asking How do I get rid of regret? we might benefit more from asking What is this mixture telling me?

Regret as a Signal, Not a Symptom

We often talk about emotions as if they were weather: moods that pass through us, storms that arrive without warning. But another way to think about them is as signals: feedback loops built into the system of being human.

Writers at Slime Mold Time Mold (thank you for sharing this blog) describe emotions not as mystical forces, but as “error signals” in biological control systems. Your body is full of feedback loops designed to keep you alive and in balance. They write, “When your blood osmolality rises, you feel thirst—that sharp discomfort pushes you to drink water. When your blood sugar drops, you feel hunger—a signal to find food.”

Emotions, in this view, work much the same way. They’re not just things that happen to us or flow through us; they’re feedback mechanisms, our own internal regulation system for how to live a good life.

Regret as an Error Signal

Seen through this lens, regret is an error signal in the feedback loop of flourishing. It tells us something is out of alignment between our actions and our values.

• When I regret snapping at my child, the signal isn’t “you’re a bad parent.” It’s “your behavior drifted from the value you hold about patience and love.”

• When I regret not preparing well for a class, the signal isn’t “you’re incompetent.” It’s “your actions fell short of your standard for teaching.”

• When I regret missing a family milestone while traveling, the signal isn’t “you don’t care.” It’s “you care deeply about family and experience—and this is the cost of your choice.”

Regret doesn’t mean flourishing has failed. It means flourishing, just like health, requires continual recalibration.

Why We Misinterpret Regret

Part of the difficulty is cultural. We’ve been taught to treat “negative emotions” as symptoms to be eliminated. Anxiety? Medicate it. Sadness? Distract yourself. Regret? Move on quickly; don’t dwell.

But if regret is a signal, then treating it like a symptom only blunts its message. It’s like turning off a smoke alarm without checking for fire. The discomfort may be gone, but the information is lost. The invitation, then, is not to banish regret but to interpret it. To ask: What is this signal pointing toward? What value feels threatened? What action drifted from what matters?

We need to be more like Kevin in his conversation with Carl—brave, kind, and willing to engage thoughtfully with regret (even when shame and fear make that hard).

Flourishing Requires Feedback

This signal-based/information-based view also circles back to why flourishing can’t be regret-free. The more we flourish, the more complex our values become. Work and family. Creativity and stability. Adventure and belonging. Each value matters. Each one can fall out of alignment.

Regret is the instrument that alerts us to that misalignment. Without it, flourishing would drift off course on autopilot. With it, flourishing remains alive, responsive, and honest. Regret’s presence is also a sign of love. You only regret what you care about. You don’t regret every misstep in life, only the ones that touch your core values. In that way, regret is also part devotion. It reveals what truly matters.

Regret isn’t the enemy of flourishing but one of its deepest companions. The more we care, the more we risk misalignment. The more we risk misalignment, the more we feel regret. And the more regret we feel, the clearer we become about who we are and what matters most.

Living With Regret While Flourishing

If regret is a signal, then the question becomes: What do we do with it? How do we live with regret in a way that deepens flourishing rather than undermines it? How do we talk about it with the people we love?

The good news is that regret, when interpreted well, is one of the most powerful tools for growth we have. Research suggests several practical approaches:

The Portfolio Strategy. Psychologists Reeck and LaBar (2024) describe regret as something best managed like an investment portfolio. Instead of obsessing over a single regret, balance the whole picture. A life is never defined by one misstep. Looking at the “portfolio” as a whole allows us to hold regret alongside achievements, gratitude, and growth.

• Pre-Mortems. Before making a major decision, imagine the regret you might feel in the future. What would your future self wish you had considered? This exercise isn’t meant to paralyze—it’s meant to clarify. By rehearsing regret in advance, we can choose with more foresight and alignment.

• Anticipating Regret for Better Habits. Research shows that simply imagining regret can improve adherence to positive behaviors—from savings plans to medical routines (Brewer, DeFrank, & Gilkey, 2016). Anticipated regret helps bridge the gap between short-term temptation and long-term flourishing.

• Anchoring in Purpose. Knowing one’s purpose matters to well-being. There will be times when regret is an unavoidable part of success. In these moments, feeling connected to something larger than oneself can center and contextualize regret. When a choice is made in alignment with deeply held values, purpose becomes the compass that steadies the discomfort, reminding us that even if the outcome carries loss, the decision itself was rooted in meaning.

Talking About Regret: Why Words Matter

Regret is an emotion that thrives in silence. Left unspoken, it can grow sharper, heavier, and lonelier. We ruminate, replaying choices in our own minds. But when regret is voiced—in conversation with a partner, a close friend, or even in a professional setting—it changes texture. Speaking it out loud moves regret from an echo chamber of self-blame into a shared space where it can be met with empathy, perspective, and even humor.

The act of naming regret isn’t just cathartic. It turns a private burden into a connective bridge. When we reveal our regrets, we also reveal our values. And when someone listens without judgment, they affirm that those values matter. This is why talking about regret can deepen flourishing: it transforms isolation into intimacy.

So how can we actually talk about regret? Here are a few guiding steps:

1. Start with Permission. Acknowledge that regret is normal. A simple statement—something like I’ve been thinking about some choices I wish I had made differently and I’d like to talk through them with you if you’re willing; not for advice, just to think out loud—opens the door without shame. It sets the stage for reflection and connection rather than advice and problem-solving (that can come later).

2. Name, Don’t Just Analyze. Share the regret without rushing to fix it: I regret missing… or I feel regret when I think back to…. Sometimes it takes a few tries to name the ache accurately—and that’s okay.

3. Invite Reflection Together. Ask: What do you think this regret shows me about what I value? How do you see me living those values, even if imperfectly? Have you ever felt something similar? These questions guide the listener’s feedback toward thoughtful empathy instead of quick advice. It doesn’t always feel great when someone—even when they mean well—tries to fix the situation too quickly. Giving them the questions you’d like them to consider, instead of just going silent, can help prevent that reflex and invite a deeper kind of reflection.

4. End with Connection, Not Closure. Regret rarely ties up neatly, but conversations can end with warmth: Thanks for listening, or It helps to know I’m not alone. Connection is the antidote to shame.

Personal Reflection Questions

If you’re not feeling ready to talk with someone about regret just yet, try exploring it privately first. Journaling can be a particularly powerful strategy to surface insight and self-compassion. Ask yourself:

• What regret do I value most for what it taught me?

• Where in my life do I have opportunities that carry the risk of regret?

• What might my future self regret if I don’t act now?

• When have I experienced flourishing and regret together—and what did that teach me about what I value?

These questions aren’t meant to eliminate regret but to integrate it—to turn regret into a companion on the path of flourishing.

I share my own regrets because I want to normalize how regret and flourishing can often coexist. And because that tension is part of being human, we need healthy ways to talk about and share it. When we keep regret hidden, it can eat at us. If regret is a teacher, the best way to internalize its lessons is to share them and teach others what I’ve learned.

And if you know someone who is struggling with regret—or if you are—consider sharing after reflection. Talk with a close friend, lover, partner, spouse, or confidant. The more we normalize the idea that achievement and prosperity can sometimes feel difficult, the better we can support one another as we walk toward and live into our values. We need other people to help us sort through the complexity of our feelings, to balance the values in play, to support us when things remain hard, and to celebrate when clarity finally begins to emerge.

The Bravery of Feeling Regret

In the end, regret can be evidence of agency. It shows that we had a choice and cared about the outcome—that we were willing to risk enough to lose something along the way.

You only regret what matters. We don’t regret every possible mistake in life—only the ones that touch our deepest values, closest relationships, and truest hopes. Regret isn’t proof of failure; it’s proof of deep care.

To long for a regret-free life is to long for a life without choices, without risks, without care. That might sound peaceful, but it isn’t flourishing. Flourishing requires regret because flourishing requires agency. And agency means some doors will close while others open, some paths will be left behind while others are taken. Values will sometimes conflict, forcing us to choose—and, inevitably, to lose. The task is not to erase regret but to accept it as part of the texture of being alive. To flourish bravely is to allow regret to sit at the table—not as a tormentor, but as a teacher.

We need to remember that this is normal so that we can frame it, talk about it, and even debate it. Regret isn’t going to stop; it’s part of success. But it doesn’t have to be the part we hide. None of us should have to be alone in our regret—or alone with our thoughts. Connection reminds us that we’re not the only ones.

As always, I want to thank Erica for walking with me through these ideas. Her questions never have simple answers, which is precisely the point. She helps me see regret not as a failure but as a form of care—an invitation to keep choosing, keep risking, keep writing.

Her editing helps me risk more honestly. Her friendship helps me regret more gently. And both help me keep going.

References for the Nerds

Beike, Denise R., Keith D. Markman, and Figen Karadogan. 2009. “What We Regret Most Are Lost Opportunities: A Theory of Regret Intensity.” Personality and Social Psychology Bulletin 35 (3): 385–397. https://doi.org/10.1177/0146167208328329.

Bradberry, Travis. 2025. “Emotions Are Rarely Pure.” LinkedIn, August.

https://www.linkedin.com/posts/travisbradberry_emotions-are-rarely-pure-many-feelings-activity-7359557748310667264-0vG7/.

Brewer, Noel T., Jessica DeFrank, and Melissa Gilkey. 2016. “Anticipated Regret and Health Behavior: A Meta-Analysis.” Health Psychology 35 (11): 1264–1275. https://doi.org/10.1037/hea0000294.

Connolly, Terry and Marcel Zeelenberg. 2002. “Regret in Decision Making.” Current Directions in Psychological Science 11 (6): 212-216. https://doi.org/10.1111/1467-8721.00203.

Lecci, Len, Morris Alan Okun, and Paul Karoly. 1994. “Life Regrets and Current Goals as Predictors of Psychological Adjustment.” Journal of Personality and Social Psychology, 66 (4): 731–741. https://doi.org/10.1037/0022-3514.66.4.731.

Lere, Joy. 2024. “No Hard Feelings: When It Comes to Difficult Emotions, the Only Way Out Is Through.” Finding Joy (blog). June 29.

Finding Joy

No Hard Feelings

Embracing All Emotions: The Path to Emotional Agility…

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2 years ago · 9 likes · Joy Lere, Psy.D.

.

Reeck, Crystal and Kevin S. LaBar. 2024. “Reining in Regret: Emotion Regulation Modulates Regret in Decision Making.” Cognition and Emotion 38 (8): 1368–1375. https://doi.org/10.1080/02699931.2024.2357847.

Richards Carl, host. 2025. 50 Fires (podcast). “Common Sense Is Controversial with Kevin Dahlstrom.” March 5. https://www.50fires.com/episodes/kevin-dahlstrom-.

Roese, Neal J. and Amy Summerville. 2005. “What We Regret Most... and Why.” Personality and Social Psychology Bulletin 31 (9): 1273–1285. https://doi.org/10.1177/0146167205274693.

Saffrey, Colleen, Amy Summerville, and Neal J. Roese. 2008. “Praise for Regret: People Value Regret above Other Negative Emotions.” Motivation and Emotion 32 (1): 46–54. https://doi.org/10.1007/s11031-008-9082-4.

Schwartz, Barry. 2000. “Self-Determination: The Tyranny of Freedom.” American Psychologist 55 (1): 79–88. https://psycnet.apa.org/doi/10.1037/0003-066X.55.1.79.

Slime Mold Time Mold (blog). 2025. “The Mind in the Wheel – Part I: Thermostat.” February 13. https://slimemoldtimemold.com/2025/02/13/the-mind-in-the-wheel-part-i-thermostat/.

In this conversation, and I, translate the research into advisor moves: prioritize one-and-done actions when motivation is high (estate docs signed, auto-saves on, allocation updated), use identity framing (“I’m a responsible investor”) over willpower scripts, and always ask about capacity before piling on tasks.

Fresh starts can spark progress—or derail what’s already working. If January isn’t it, pick the next landmark (tax day, anniversary, birthday) and plan around it. Practical prompts inside, plus how to document personal landmarks in your CRM so you can time advice when it lands best.

The Takeaways

• Use fresh starts for one-and-done wins (bank the momentum).

• Switch to identity language: “I’m good with money,” not “I should…”

• Check capacity before action—prevent motivation whiplash.

• Create auto systems (auto-saves, allocations) while motivation is high.

• Don’t break good streaks—fresh starts can backfire mid-season.

• Personalize landmarks (birthday, anniversary) and log them in your CRM.

Support Us

There are now officially four of these little chats and we have four more recorded. and I love doing this work, but it also helps to have your support. If you can, please subscribe to (Less) Lonely Money as a paid subscriber—only $149 for the year. You get additional advisor-focused content.

What more support from myself and Ashley? Check us out at Beyond The Plan(R). We work with individual advisors and their firms to help integrate behavioral finance and financial psychology.

Welcome to this month’s drop from (Less) Lonely Meetings—a toolkit for turning each (Less) Lonely Money article into real, relationship-centered conversations.

Inside, you’ll find two ready-to-use tools:

• Client Companion – A reflection-first newsletter you can send to clients and prospects, sparking meaningful dialogue and building trust.

• Meeting Ready – A practical guide designed to help you bring this month’s themes into your next 30-minute meeting—without scripting or overhauling your process.

This month, we explore uncertainty—why our brains crave certainty, why it’s so hard to find, and how we can respond differently. Rather than rushing for answers, what if clients practiced experiments, patience, and connection as tools for meeting the unknown?

These aren’t sales prompts. They’re conversation starters.
Because every good plan starts with a good question.

Client Companion – This Month’s Client-Facing Newsletter

Newsletter Title: Forego the Quest for Certainty: Why Living with the Unknown Might Be the Bravest Skill We Have

Best Used:

Before market updates • In the midst of volatility • During career/life transitions • As a reflection piece for prospects considering financial planning

Suggested Subject Lines:

• The Illusion of Certainty (and What to Do Instead)

• Why “Not Knowing” Can Be a Strength

• How to Live Well in the In-Between

Optional Intro Advisors Can Use:

We all want answers—especially about money. But what if chasing certainty is keeping us stuck? This reflection offers a different way to meet the unknown: through patience, experiments, and connection.

Full Text (Just Copy/Paste into Email)

Forego the Quest for Certainty: Why Living with the Unknown Might Be the Bravest Skill We Have

Most of us crave certainty. We want to know the market will recover, the job will work out, the retirement plan will hold. We want guarantees before we commit. But the truth is, certainty is rarely available—and never guaranteed when it comes to money or life.

What we can do is choose how we respond.

Psychologists point out that anxiety thrives on the unknown. The more unpredictable something feels, the louder our minds demand answers. Our instinct is to reach for more information—refresh the market app, check headlines, scroll through financial commentary, ask Google one more question. But information doesn’t always bring peace. Often, it just feeds the cycle.

We can’t escape uncertainty, but we can learn to live differently with it.

Here are a few practices that help:

• Practice patience like a craft. Patience isn’t just waiting. It’s the discipline of staying present even when the outcome is unclear. In financial life, that might mean holding steady in a volatile market instead of rushing to change strategy, or giving yourself more than one conversation before making a big decision like downsizing your home. True patience is active—it’s noticing, listening, and giving decisions space to breathe.

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