Why Mastery in Investing Is a Lifelong Journey

If there’s one thing I’ve learned in over four decades of investing, it’s this: mastery is not a destination. It’s not a trophy you earn and put on the shelf. It’s not a box you check off after you’ve read the right books or nailed a few big wins. In fact, I’d argue that the moment you think you’ve mastered investing is the moment you start getting lazy—and maybe even dangerous.

I’m in my last 70's, and after 44 years of doing this full-time, I still find myself learning something new all the time. That’s not a flaw of the system—it’s the beauty of it. Investing, at its best, is a lifelong pursuit. It’s a journey that evolves with you. And that’s what keeps it so compelling.

Groundhog Day and the Joy of Endless Learning

There’s a lesson in the old Bill Murray movie Groundhog Day that has stuck with me. In the film, the main character is trapped reliving the same day over and over. At first, he tries everything to escape the loop—self-indulgence, shortcuts, even crime. But eventually, he turns inward. He starts learning. He picks up piano. He helps people. He refines his character.

What changes his life isn’t escaping the repetition—it’s learning to love the process of becoming. And in many ways, that’s what investing is. A pursuit where you’re never really “done,” but always refining your understanding. That’s what makes it deeply fulfilling. Not unlike learning an art form or a craft that you never fully conquer.

You Can’t Quant Your Way to Certainty

We were talking recently with the team about what makes a business “wonderful.” Sure, we have frameworks and checklists. We define a wonderful business as one that’s protected, durable, and likely to be significantly bigger 10 years from now. But even with decades of experience and pages of financials, it’s never an exact science.

There’s always that urge to find the magic set of numbers that tell you with certainty: this business is going to thrive. We all want that shortcut. But Buffett put it plainly—if investing were just about reading historical numbers, all the librarians would be rich.

Numbers matter, no doubt. But they aren’t the whole story. Qualitative judgment—your ability to understand a company’s business model, moat, management, and meaning—matters just as much, if not more. It’s a dance between the left brain and the right brain. And that dance never stops.

Warren, Charlie, and the Expanding Circle

Charlie Munger once said Warren Buffett is a “learning machine.” And it’s true. Warren didn’t just stick to the cigar-butt investing of his early years. Over time, he adapted. He learned. He grew his circle of competence—and picked up Apple at just the right time, something his younger self might’ve never done.

That’s a great lesson for all of us. You start in one small circle—maybe you understand a certain industry or use a particular product. And as you study one company, you inevitably bump into others: competitors, suppliers, customers. Before you know it, your circle gets bigger.

The trick is to stay within your current circle while steadily stretching it. Don't leap into a business you don’t understand. But don’t be afraid to learn and grow either. That’s where real confidence is built.

Just One Thing: Focus and Depth Over Breadth

There’s a line from City Slickers that has always stayed with me. Jack Palance’s character tells Billy Crystal’s character the secret to life is “just one thing.” When pressed on what that one thing is, he simply says, “You’ve got to figure that out for yourself.”

That concept—focus—is incredibly applicable to investing. You don’t need to know everything. In fact, trying to know everything will leave you overwhelmed and scattered. But you can get really good at understanding one business. Learn its ins and outs. Know its competitors. Watch how it responds to events and earnings. Treat it like a craft.

It’s much more attainable than trying to become a master stock picker overnight. And the confidence you build by going deep in one area will carry over into others.

The Humility of Practice Shares

Danielle and I have talked about this over the years—how powerful practice shares are. The moment you put even a small amount of real money behind a company, everything changes. Doubts flood in. Questions arise. Someone asks about your investment and suddenly you’re fumbling for words you thought you understood.

That’s good. That’s part of the process. Practice shares expose the difference between theory and application. They teach humility. They force you to admit what you don’t know—and go learn it. We use them regularly in the fund. It’s one of the best ways to level up.

Holding On vs. Letting Go

Now here’s where mastery gets tricky: knowing when to sell. I’ve made some big mistakes in this area—not because the companies went bad, but because I sold too soon. I got out after a double, when they went on to 10x. That’s the cost of trying to optimize velocity in the early years. A habit I’ve worked hard to break.

On the flip side, there are times when a company hits a real issue, and you have to act. But most of the time, if you’ve done your homework, you should trust the process. I often say: buy wonderful companies on sale and don’t lose money. That’s Rule #1. But I’ll also say this: if you hold those wonderful companies long enough, your wealth will grow in ways you never imagined.

Mastery Is the Mirage. The Journey Is the Point.

At the end of the day, we’re all chasing something that’s just out of reach—and that’s the point. Mastery in investing isn’t about arriving at a final destination. It’s about walking the path, one decision at a time, refining your craft, staying curious, and building wealth through understanding.

And if you do it the Rule #1 way—buying great businesses at attractive prices, staying within your circle of competence, and learning from every mistake—then even without perfect mastery, you will almost certainly become wealthy.

And that’s a journey worth taking.