A good investment still needs time. Compounding cannot work on what an investor will not hold!

Long-term results often look boring at first. Patience gives compounding time to become visible!

The best investment may be the one you can leave alone.

Diversification requires the humility to own something you dislike because you can't know what the future will favor.

A good story can make hope sound like research!   A smart friend told you about it, you read an article, you think you can explain why it should go up…   But before you invest, ask yourself, “What do I actually know?”   The market doesn’t care what we hope will happen. This sketch is from my latest book, Your Money. You can order a copy for yourself here or anywhere you love to buy books: buff.ly/j9m6POP To order in bulk as gifts for clients, colleagues, or friends, use this link to get an additional 5% off U.S. bulk orders with the code: YOURMONEY5. buff.ly/AzNCmFh Leave a copy on your coffee table, in your conference room, or in the hands of the people who trust you!

When an investment has been doing well, buying it feels sensible. You have proof. You can see the results! The problem is that all the proof is behind you. Past performance is information. It isn’t a plan.

We buy high and sell low, even though we know better.   At the top of the market, we can’t buy fast enough. At the bottom, we can’t sell fast enough.   Repeat until broke.   This behavior is normal, but acting on it can cost a lot!   My latest book, Your Money, was written for everyone brave enough to break the silence around money.   📚 If you’d like copies for your team, clients, or for the attendees of your next event, you can place U.S. orders in bulk at a discounted rate here: buff.ly/L8ORbhz   Use the code YOURMONEY5 for an extra 5% off.   Outside the U.S.? Email hello@thesocietyofadvice.com, and the team can help with a bulk order.

There’s a difference between what an investment earns and what an investor actually gets. The return can happen. And we can still miss it. Usually because we weren’t there long enough to receive it! That’s what I like to call The Behavior Gap.

Clients often ask, “Should I spend less?” Sometimes the better question is: “Is this way of spending actually giving you what you want?” That question changes the conversation. This idea comes from my new book, Your Money: Reimagining Wealth in 101 Simple Sketches.   Want a copy?   📘 Order a copy for yourself on Amazon or your favorite bookstore buff.ly/kHLquwo 📚 Order in bulk to hand out to clients, prospects, or friends. Use this link to order and get an additional 5% off bulk orders (U.S. shipping only) with the code: ADVISOR5. buff.ly/BjBaO2g 🌎 If you're outside of the United States and would like to place a bulk order of 25+ copies, email the team at hello@behaviorgap.com.   Leave a copy on your coffee table, in your conference room, or in the hands of the people who trust you!

Put this sketch in front of a client who feels guilty about spending and ask, “Does this line up with what matters most?”

When you tell yourself, “Don’t look, don’t look, don’t look,” but you still look. Sometimes the move is to redirect.

When it comes to experiences with people you love, spend the money. Not every time. Not without thinking. But more often than your spreadsheet might suggest. 📚 This sketch is from my latest book, Your Money: Reimagining Wealth in 101 Simple Sketches. Order your copy here: buff.ly/t9S8B0B

Cheap things can cost us money. They can also cost us time, attention, and hassle. That part matters, too. → This sketch comes from my latest book, Your Money: Reimagining Wealth in 101 Simple Sketches. You can order it wherever you buy books, or here: buff.ly/GjHJgyx

At some point, the research costs more than the thing. Just pick one and move on.   From my new book, Your Money: Reimagining Wealth in 101 Simple Sketches: buff.ly/GjHJgyx

Most financial goals sound exciting in the beginning.   💪 Retire early. 🌎 Travel more. 💰 Give more away.   But for Real Financial Advisors, almost every meaningful financial goal eventually runs into the same question: 👉 How’s the cash flow?   That’s not just math. That’s behavior!   It's where values become visible, where the real work lives.   These are the kinds of conversations I love having with advisory firms, leadership teams, and conference audiences. If you’d like me to speak at your next event, my team would love to help make it happen. 💌 Email hello@behaviorgap.com and let's talk.

Most people think saving money starts with restriction. Sometimes it just starts with noticing. One small positive outcome changes what feels possible. That’s why tiny wins matter so much with money.

We tend to think big goals require big action. But most of the time, progress starts with one small move. Saving for college feels overwhelming. Finding an extra $100 does not. That’s the power of a micro-action. 💪 It creates momentum, and momentum has a way of spreading. Start there. Then see what happens next. This sketch is from my new book, Your Money: Reimagining Wealth in 101 Simple Sketches. If you’d like copies for your team, clients, or for the attendees of your next event, U.S. orders have a discounted bulk rate here: buff.ly/Wrqn78Q. Use the code YOURMONEY5 for an additional 5% off.

The next smallest action is usually smaller than you think. That’s why it works.

My next Weekly Letter "No… smaller than that." is coming tomorrow May 28. Subscribe to get it and stay in the loop on everything I'm creating. buff.ly/mUtRmm1

Every dollar spent is a tiny vote for what matters to us. That’s true whether we notice it or not. Our spending shapes our values, too.

Every financial decision is a tradeoff.   It's not about right or wrong. Or good or bad.   💥 It's present vs. future.   We don’t always say it that way, but that’s what’s happening.   Once you see it, things get clearer. You stop looking for the perfect answer.   You start asking a better question: 👉 What am I trading away to get this now?   I wrote about this idea in Your Money: Reimagining Wealth in 101 Simple Sketches. If you like my work, I think you'll love this new book. Order a copy from your local bookstore here: buff.ly/pqdwHmh

We talk about goals like they need to be precise, clear, and certain.   But most goals start as a guess.   They are a guess about what will matter. A guess about what the future might look like.   And that’s okay.   👉 You don’t need perfect goals. You need a current guess.   That’s one of the ideas inside my new book, Your Money. If you haven't picked up your copy yet, you can do that here: buff.ly/QwH0YNn

It’s easy to get pulled in a lot of directions.   …What you should want. …What you should be doing. …Where you should be by now.   Pretty soon, it’s hard to tell what’s yours and what isn’t!   👉 So here’s a simple reminder today: The only goal that matters is yours.   Sounds simple, but it’s not. It takes a little work to even know what that is!   That’s the question behind one of the sketches in my new book, Your Money.   The book is full of better questions that are worth talking through with someone else. If you like my work, I think you'll love the new book. Order it here: buff.ly/Z507RkM

💥 Enough is not a number. Clients often ask how they’ll know when they have enough. There’s a version of that answer that lives in a financial plan. You run the numbers, you look at the projections, and someone tells you, “You’re going to be fine.” That’s helpful... But it’s also a little misleading. Because the moment you pick a number, it has a way of moving. I’ve seen it over and over again. One more year and one more dollar. Just a little more. It doesn’t stop. So I’ve come to believe that enough isn’t something money can solve. We’ve given money a job it can’t do. Just like it can’t deliver happiness or self-worth, it can’t tell you when you have enough. 👉 That turns out to be a different kind of work. And here’s the part that surprises people... 💥 The same habits that helped you build wealth, discipline, saving, working hard, can actually make it harder to feel like you’ve arrived. They were exactly what you needed in one phase, but they don’t always serve you in the next. At some point, the work changes. It becomes less about building and more about learning how to use what you’ve already built. That doesn’t happen all at once. In fact, it usually feels uncomfortable at first. So you practice. You start small. ✨ You spend a little in ways that feel meaningful. You take the trip. You buy the gift. You create experiences with people you care about. It sounds simple, but it’s not easy. Because in the end, this isn’t really a financial problem. It’s learning how to recognize when you already have enough 💪

Financial planning isn’t a one-time event. It’s a lifelong process.   And it keeps coming back to three questions: …Where are you today? …Where do you want to go? …How will you get there?   My new book, Your Money, is just a collection of ways to sit with these three questions a little longer.   If my work has been useful to you, tell three people about it.   You don’t need to explain it.   “This made me think of you,” and the link to the book is enough → buff.ly/AQTgu6L   Over the last couple of decades, that’s how my work has spread. One person helping another person take the next step.   Thank you for being part of it.

Most of what you’re worried about right now… you can’t control. Years ago, I drew a simple sketch with two circles. Things you can control. Things that matter. 🎯 The overlap is where your attention belongs. When your circle of concern gets bigger than your circle of control, you feel it. So I come back to a simple question: 💪 Does it matter… and can I do anything about it?

It’s been about six months since my latest book, Your Money, came out. buff.ly/AQTgu6L   I’ve been thinking about what success looks like. For me, it’s not sales or rankings. 💥 It’s conversations.   I’ve heard from readers using the book in ways I never would have imagined.   …Friends picking a sketch and talking about it over dinner. …One reader uses it each morning. …Another is going through it with their kid, one sketch a week.   That was the whole point. You don’t have to read it front to back. You don’t need a plan. One sketch is enough.   The one in this post is a good place to start.   👉 It's just one word: Why.   Most of us skip "why" and go straight to "what" and "how," but "why" is the part that gives everything else meaning.   Try this: 1- Pick one sketch. If you don’t have the book, use the one in this post. If you have a copy of Your Money, open it anywhere and start there. 2- Use that sketch to start one conversation about money. 3- Then listen.   And if you’re up for it, email me at hello@behaviorgap.com and tell me what happened. I read every message.

A budget isn’t about restriction. It’s about noticing. What did you just spend money on… and did it feel like a good trade? This idea is from my new book, Your Money.   Pick up a single copy here: buff.ly/jdrn2AX   Or if you’re ordering copies for a team, firm, or event, you can get an additional 5% off bulk orders (U.S. shipping only) with the code ADVISOR5 here: buff.ly/gBHEWQ1

A Real Financial Advisor's value often lives in one thing… 👉 Creating a little space between what happens and what a client does next. That space changes everything. But it’s small and easy to miss. And yes, it’s hard. That’s the work, and that’s why we practice. I wrote about this in my new book, Your Money. If you haven't picked it up yet, you can order a copy from your local bookstore here: buff.ly/NCjbRlo

What matters and what you can control. The work is in the overlap. This is sketch 22 in my new book, Your Money: Reimagining Wealth in 101 Simple Sketches. If you like this sketch, I think you'll love the entire book. buff.ly/pVEGGDC

A lot of financial stress comes from trying to evaluate every opportunity that shows up. A simple plan filters most of them out. Mine fits on one card: 💪 Time with my family, mainly outside, and serving in my community. When something new appears, I ask one question: Will this get me closer to what matters most? This idea appears as sketch #21 in my new book, Your Money: Reimagining Wealth in 101 Simple Sketches. If you haven't yet, you can pick up your copy here: buff.ly/3kiffEo Something to sit with today... If you wrote your One-Page Financial Plan, what would it say? 💥

Enough is a decision.

For years I have been talking about something I call a "Real Financial Professional." 📈 Not a product salesperson. 🗺️ Not a defender of an outdated map. 🥾 A guide in a changing landscape. Someone who helps people align their time, money, energy, and attention with what actually matters to them! That work is harder than most people realize. It requires technical skill, emotional awareness, and the ability to sit with uncertainty alongside your clients. It is not about being precisely right today. It is about helping people be less wrong tomorrow. A few years ago I wrote a Manifesto about what this work really means. If you care about the craft of advice, I think you’ll appreciate it: 👉 thesocietyofadvice.com/manif…

Before you replay the mistake again, ask: Would I judge someone else this harshly for the same thing? If the answer is no, that’s useful information. This sketch is from my book, Your Money. It’s about noticing the stories quietly shaping our decisions.   📚 You can pick up a copy at your local bookstore or wherever you buy books: buff.ly/SDQF3Xb

You can’t make it too simple. Most of us in this industry are really good at complex things. We’ve “Kitces-ed” it to death. Big spreadsheets and more and more technical precision. That’s required. But here’s what’s easy to forget: Most clients don’t know what you mean when you say volatility. And they won’t tell you. They’ll nod. They’ll say yes, yes, yes. Then they’ll go home and think, “I don’t know what she just said, but she seems smart.” 🤷 We use words like "risk" and mean standard deviation within known bounds. A dial we can turn up or down. Our clients hear risk and think, “Am I going to end up under a bridge?” Same word. Completely different meaning. Keeping jargon out of conversations is like weeding a garden. It never ends. You have to stay vigilant. There’s a difference between simplistic and elegantly simple. Simplistic ignores complexity. Elegantly simple earns its way there. You’ve been through the edge cases. You’ve done the hard thinking. And you come out the other side and say, “Here’s what matters.” 🎯 That’s what clients pay Real Financial Advisors for. If you’re tired of hiding behind complexity… If you know you’re good at the technical work but want to get better at the human work… If you’ve felt that gap between what you know and what your clients actually hear… 💥 That’s exactly what we work on each month inside The Society of Advice. The Society of Advice is where financial advisors gather to practice the craft that can’t be automated. It’s a live, monthly conversation curated by me and featuring a guest worth paying attention to. Advisors who care about this work show up for it. No extra noise, just the REAL work on how to make things clear, human, and useful. If that’s the kind of advisor you’re becoming, you’ll feel at home here. Join us for the next live conversation: 📆 Thursday, March 26, 2026 ⏰ 11:00 a.m. Eastern for 90 minutes 👉 Register: thesocietyofadvice.com/

After our May 2025 workshop, @TimMaurer and I recorded an extra 30 minute follow-up. We answered the questions from advisors that we didn’t get to live in the private 90 minute conversation. We talked about things like... • Money scripts. • Client honesty. • When tactics become a hiding place. • Why simple visuals work. • Why becoming a better Real Financial Advisor starts with being a better human 💥 We decided to share that 30-minute follow-up conversation publicly: piped.video/ghYNZFS66Vs The full 90-minute workshop is gone. We don’t keep an endless archive at The Society of Advice. But the next live conversation is happening in March. I've noticed that most advisors don’t need more tactics. They need space to think. If you’re feeling pressure from AI, the answer isn’t to race it. It’s to become more human. Each month I curate and host one 90-minute conversation specifically for your work as a Real Financial Advisor. There is no prep work needed from you, and there's no homework. You are not signing up for a content treadmill with an endless archive of recordings to watch. This is clarity work. Live. A conversation hosted by me and featuring a guest whose thinking is worth your attention. 👉 Join us for the next conversation: thesocietyofadvice.com

A lot of us say we just want to get ahead. But most of us have never stopped to ask what that actually means.   If we never define what “ahead” means, we end up in a race that has no finish line. This sketch is a reminder that “enough” requires a decision.   If you like this sketch, I think you'll LOVE the entire book. Your Money: Reimagining Wealth in 101 Simple Sketches is available at local bookstores here: buff.ly/9SNUSrH   Sometimes clients say they just want to “get ahead.” That’s usually a signal, not a strategy. This sketch creates space to ask the better question: What does "ahead" mean to you?   If that sounds useful, you can license this sketch and use it as the foundation for your next client newsletter. 👉 buff.ly/5F0uZDP

Lifestyle creep rarely announces itself. It usually sounds reasonable. It usually feels earned. Until we realize the goalposts moved… again. This sketch maps that pattern. It’s from my book, Your Money, where my goal was simple: to help you see what’s really driving your next money decision. 📚 You can pick up a copy at your local bookstore using this link: buff.ly/9SNUSrH

If you’re a financial advisor and something about this industry feels off to you, you’re not alone 🖤 I wrote The Manifesto as a line in the sand. ...We are not salespeople. ...We are not asset gatherers. We are stewards of decisions that shape lives! If that lands with you right now, I'd like you to read the digital copy of The Manifesto: thesocietyofadvice.com/manif… It's free and I think you'd love it.

One of the hardest parts of writing to clients is knowing how to start. This sketch solves that problem. It opens a thoughtful conversation about comparison and identity without explaining, persuading, or overwhelming. Remind clients: If money has felt heavier than usual, notice where comparison shows up. If you’re a financial advisor, you can license this sketch and use it as a simple entry point in your next client email. buff.ly/aOYkmPq Because “I wonder how much they make” is rarely about the number. It’s about what we think the number says about us. It’s all about slowing down the thoughts that quietly drive our money decisions.

For ten years I wrote a weekly column for the New York Times. Each one had a simple sketch. Readers started emailing in, but they didn’t say the sketches were beautiful. They said something even better... “I put it on the fridge.” “I hung it in the break room.” “You wouldn’t believe the conversations it started.” Sketches weren’t just art... They were tools! You drop one of these into a room and conversations break out. I started calling them conversation grenades. These conversations are the reason for the new book, "Your Money: Reimagining Wealth in 101 Simple Sketches." 📚 Grab your copy from your local bookshop using this link or get it where ever you buy your books bookshop.org/p/books/your-mo… If you’re thinking about sharing the book with a team or clients, bulk copies are available. Get an additional 5% off bulk orders (U.S. shipping only) with the code ADVISOR5. bulkbooks.com/products/your-…

We all carry an invisible number above our head. At some point, the number stops being information and starts being something we defend. We protect it. Grow it. We become obsessed with comparing it. That’s rarely where clarity lives. 👉 You can pick up your copy on Amazon or wherever you buy books. buff.ly/QkAWVWg   If you’re in the U.S. and ordering for a firm, team, or event, you can purchase bulk copies at a discount here: buff.ly/nPFjTsI

Most conversations about taxes start too late. This sketch shows the difference... On the left are the taxes you paid. On the right are the taxes you could have paid. That gap is not about loopholes or clever reporting. It is about planning... or the lack of it. Good tax work happens upstream. Before the sale. Before that big decision is final. Once you see this distinction, it is hard to unsee it. And it changes how you talk with clients about what actually matters. → This sketch is available as a digital license if you want to use it in client conversations, presentations, or internal training. This art is meant to be used. store.behaviorgap.com/produc…

Most of the damage in scary markets is not market damage. It’s behavior damage. Your clients do not call because they want more data. They call because they want relief. They want someone steady on the other end of the line. 💪 I put together a "Guide to Scary Markets” for that exact moment. Two short videos... One is a quick heart to heart between you and me. The other is word for word language you can use with a client who is tempted to do the big mistake. If you want it, it’s here and it's free: 👉 thesocietyofadvice.com/scary…

If money feels heavier than it should, pause and ask yourself, "Who am I comparing myself to right now?" Many times, the pressure isn’t about the numbers at all. This sketch is one of the 101 in my book Your Money. The book isn’t about telling you what to do. It’s about helping you notice what’s actually driving the decision so you can choose more deliberately.   → You can grab your copy here or wherever you buy books. buff.ly/r5tLBP5

If a money decision feels heavier than it should, pause for a moment. Who are you comparing yourself to? And is that the right comparison set for you? That question alone can change the conversation.

I left this sketch without words on purpose. When people bring their own meaning to it, the conversation gets better. It leaves room for you to see what you need to see. 📚 This is the third sketch in the new book. Grab your copy here: amazon.com/Your-Money-Reimag…

Shame doesn’t help us think clearly about money. Neither does blame. Curiosity does. My new book is simply a longer conversation along these lines. It’s called Your Money, and it's available here 👉 buff.ly/bjsHsmS

There isn’t a right way to do money. There’s your way and my way. Some choices look like bad business advice and still turn out to be the best decisions we make.

It's normal for clients to be tempted to make "The Big Mistake" when markets get scary. Often, as a financial advisor, you are the only thing preventing them from doing so. But it's a tricky conversation. → How do we help clients make rational decisions aligned with their values and goals when everything around them is irrational? Here are my scripts: thesocietyofadvice.com/scary…