Tuesday Email: Beginner's Mind in an Expert's World

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

There is a major paradox in wealth management.

We treat experience as the ultimate credential. More years equals more trust. Twenty years in the business and we've earned our stripes.

Or so we think.

What the research shows, and what I've seen play out in conversations across this industry, is that the longer we are in practice without intentional, deliberate disruption, the more rigid our thinking becomes.

This isn't just an advisor thing. It's a professional services thing.

Expertise without deliberate practice is a slow drift towards irrelevance.

Before we all get defensive: this is a structural flaw, not a character flaw.

Erik Dane defines cognitive entrenchment as a high level of stability in an individual's domain schemas. In plain terms: where we work, what we do, how we do it. When we repeatedly retrieve and apply the same specialized knowledge, the way we work stabilizes to such a degree that revising it becomes highly unlikely. Awareness of this challenge is what gives us the power to overcome it. For the betterment of our firms. For the betterment of our clients.

It breaks down into three dimensions.

Cognitive entrenchment. The first time you execute something, you are highly aware of every step. You check the checklist. You are fully in tune with what you're doing. The second time is about the same. The third, a little less. By the hundredth time, you are not engaged with each individual step anymore. What was once five distinct steps has become one thing. Just doing the thing. They've all melded together. And when a process becomes one seamless gesture, it is nearly impossible to examine it. Let alone improve it.

The curse of knowledge. Because the process feels like one thing, we can no longer break it apart. And because we know it so completely, we assume everyone else sees it the same way. They don't.

One of my favorite studies is this study that includes individuals who tap out a melody and then a set of individuals who listen to the tapping and try to guess the melody. The tappers were tasked with tapping out 120 well-known melodies. Just finger taps. No humming, no melody, just the beat. The tappers predicted that listeners would correctly identify 50% of the songs. In reality, listeners got 3 out of 120. A 2.5% success rate. The tappers had the full arrangement playing in their heads. The listeners heard disconnected taps. Same exchange. Completely different experience.

In every conversation we have with others, whether it’s clients or peers, we are the tapper. The other person is the listener. With our clients we hear the full symphony of the financial plan, the reasoning, the tradeoffs, the sequencing. They hear taps. This is why a beginner's mind matters. Not as a soft concept. As a communication discipline. We have to work to understand what someone else is actually receiving, not just what you intended to send.

Automaticity. Another study I find valuable is one that extended over 18 years and monitored psychotherapists. It was designed to track how patient outcomes changed as therapists gained experience. The findings from the study were not what we would have predicted. Despite nearly two decades of experience, the average objective outcomes for experienced therapists remained flat or deteriorated. Why? Because the way they worked became automatic. They never took deliberate action to examine, alter, and evolve their approach. The complexity of the world grew. The simplicity of their habits didn't keep up.

The moment we go on autopilot is the moment we start to decline.

We are never standing still. We are either progressing or we are declining.

The best practitioners in any profession have figured something out. None of them found it in a book or at a keynote. They found it by changing how they think about interesting questions.

Edwin Land was on vacation in New Mexico with his family in 1943. They were taking pictures. His three-year-old daughter asked the question any parent with a camera (before Iphones) has fielded. "Why can't we get the pictures right away?" Land could have answered the way most of us would have. That's just the way it is.

Instead, he sat with the question. He went on a walk. He asked why. He asked what it would need to look like. That question, a child's naive, expert-free question, sparked the invention of the Polaroid camera.

Jony Ive, who was central to developing the iPhone, talks about moving between two modes: curiosity and resolve.

Curiosity is open, exploring, questioning. Resolve is committed, determined, executing.

What made Ive exceptional is that he oscillated between these two states multiple times in a single day. Most people with deep expertise lose access to the curiosity mode. Experience starts to feel like the answer. Possibilities start to feel like a younger person's game. The best professionals never let that happen.

I'm a big golfer.

I've worked my handicap down to a number I'm proud of. And for a long time, I never wanted to touch my swing because I feared losing what I had. I liked where I was. I had ambition to improve, but I kept having short bursts of progress followed by a return to the same level. I never committed to a real swing change because I feared the short-term deterioration more than I believed in the long-term gain. Loss aversion. Fear of the unknown being greater than dissatisfaction with the known. Overconfidence in where I already was.

Recently I started working on it. I've found it and I've lost it. But I'm making real progress toward long-term improvement. And it required getting worse before getting better. That's the deal.

When I started our technology company, we built our initial thesis entirely on my experience. Six or seven years in the business, years of watching my father build the firm. I was confident I knew what the industry needed. We spent real time, money, and effort building the product I had envisioned. We waited to get it into people's hands. By the time we did, so much had been invested that it needed to be right.

It wasn't.

The way they worked, the desires they had, the needs they were trying to meet — our product didn't serve any of it. And because we had waited so long to test it, changing direction was exponentially harder. That experience changed how I think about building anything. The best innovators don't anchor their beliefs to their experience. They experiment early. They experiment often. They get it into users' hands before it's finished and let what they learn reshape their assumptions. I've operated that way ever since.

Most of us are already using AI meeting note-takers. This coming week, I challenge you to put them in every meeting for the next 3 days.

Internal meetings, client meetings, all of it.

Then actually analyze the output. Use AI to help you analyze the output.

Look at your talk time versus everyone else's. Look at how many questions you asked versus how many statements you made. Were you a questioner or a stater? Some note-takers surface this automatically. If yours doesn't, drop the transcript into an AI tool and ask it.

For me, I'm a stater. I like to talk in meetings.

I've realized that's not always the best thing. I need to ask more questions.

Becoming self-aware of it has already started to change how I show up. That's the point of the exercise. Not to transform overnight. Just to see yourself clearly.

The goal isn't to become someone you're not. If you're already a questioner and a listener, make sure you're not drifting from that. If you're a stater, start noticing it in real time. Self-awareness is the entry point. You can't change a habit you haven't named.

A beginner's mind is not about being less expert.

It's about not letting your expertise become a ceiling. Expertise without deliberate practice drifts towards irrelevance.

The Futureproof advisor who will win over the next decade isn't the one who knows the most. It's the one who stays genuinely curious while everyone else coasts on credentials.

Go earn the stripes. Just don't let them stop you from being curious.

The best is ahead!

-Matt