Master of None

Second Level Thinking · Issue 48

Why having too many interests isn’t the liability you’ve been told — and may be the best problem you’ll ever have.

I’ll start with a confession. At any given moment I am running an advisory firm, writing this newsletter, building a leadership course, picking up a guitar I should probably put down, hunting for vinyl I don’t have room for, and butchering my way through beginner Greek. Some common phrases come to mind regarding this: Focus. Do one thing properly. Jack of all trades, master of none.

It begs the question, is it better to pick a lane or is it ok to wander?

For a long time I believed the former but I have come to believe the opposite. Not as a comforting story I tell myself, but as something the evidence increasingly supports. If you are someone with too many interests, too many half-finished curiosities, too many things you love to be able to name just one — I want to make the case that you are not scattered. You are not behind. You may, in fact, be holding one of the best problems a person can have.

Kind worlds and wicked ones

The most useful framework I’ve found for thinking about this comes from David Epstein’s Range: Why Generalists Triumph in a Specialised World — a book I’d put on the short list for anyone who has ever felt guilty about their own curiosity.

Epstein opens with two athletes we all know. Tiger Woods, swinging a club before he could properly walk, the patron saint of early, narrow, total specialisation. And Roger Federer, who as a kid played football, basketball, badminton and skied. Roger didn’t commit seriously to tennis until well after the age the experts say is already too late. Two of the greatest ever. Two completely opposite paths. We’ve built an entire culture around the Tiger story and quietly ignored the Roger one, because the prodigy who knew his destiny at a young age, makes a tidier headline than the kid who mucked about with everything first.

The deeper idea underneath this is the distinction Epstein borrows between kind and wicked learning environments. A kind environment has fixed rules, repeating patterns, and quick, honest feedback, like; chess, golf and learning musical scales. In those, it pays to specialise early and drill hard; the ten-thousand-hour story holds. A wicked environment has shifting rules, fuzzy or delayed feedback, and situations you’ve never seen before. And here’s the thing: almost everything that actually matters — building a business, leading people, raising children, investing, navigating a career across forty years — is a wicked environment.

In the kind world, the specialist wins. In the wicked world — which is to say, most of real life — it’s the person with range who tends to come out ahead.

Why? Because in a genuinely novel situation, narrow expertise can become a trap. The specialist reaches for the one familiar tool. The generalist, who has wandered through many rooms, can ask: this reminds me of something from over there. Epstein’s word for the deepest version of this is match quality; the fit between who you are and what you do. His finding is that the people who sample widely before committing, tend to find far better matches than those who locked in early, even though they look “behind” for a while. The wandering isn’t lost time. It’s how you find the thing worth not wandering from.

You’re not a jack of all trades. You’re M-shaped.

There’s a video by Sandeep Swadia on YouTube that reframes this beautifully. He talks about moving from a T-shaped person to an M-shaped one.

The T-shaped person has one deep spike of expertise and a thin bar of general knowledge across the top. That was the aspirational model for years. But the future, Swadia argues, belongs to the M-shaped person — someone with several peaks of real depth, connected by a web of breadth underneath. Not a dabbler with a dozen shallow puddles, and not a monomaniac with one lonely spike. Multiple genuine competencies, joined together, each one making the others sharper.

That reframing did something for me. Because the fear of having too many interests is really the fear of being shallow everywhere and deep nowhere. But that’s not what’s actually being described. The goal was never twelve hobbies you’re mediocre at. It’s a handful of things you’ve gone genuinely deep on, plus the connective tissue between them — which turns out to be where most of the interesting value in the modern world is created.

The connection is the whole point

This is the part the specialists’ world systematically undervalues: the most original work tends to happen at the intersection of fields, not the bottom of a single well.

Steve Jobs sat in on a calligraphy class he had no practical use for, dropped out, and a decade later it became the typography that set the Macintosh apart — he later said if he’d never wandered into that room, personal computers might never have had beautiful type. Charlie Munger built one of the great investing minds of the century not by studying finance harder than everyone else, but by assembling what he called a “latticework of mental models” borrowed from psychology, physics, biology, and history. The author Frans Johansson named this the Medici Effect, after the Florentine family who pulled sculptors, scientists, poets and financiers into the same rooms and accidentally lit the Renaissance — innovation exploding precisely where disciplines collided.

Range isn’t a consolation prize for people who couldn’t commit. It’s the raw material of connection. Every extra field you wander into is another set of analogies, another way of seeing, another tool in the kit for the moment the wicked world throws you something genuinely new.

And if you think you’ve started too late

There’s a quieter fear buried under “too many interests,” and it’s about time. The sense that the clock’s run out, that the people who picked early have an unassailable head start.

So let me just lay out a few facts, plainly. Ray Kroc was a fifty-two-year-old milkshake-machine salesman when he walked into a burger stand in San Bernardino and built McDonald’s. Henry Ford was forty-five at the Model T release. Samuel L. Jackson got his breakout role at forty-three.

And the people who didn’t start late but simply refused to do one thing? Leonardo, who couldn’t decide between painting, anatomy and engineering and became the era’s definition of genius. Benjamin Franklin — printer, writer, diplomat, and the man who pulled lightning out of the sky with a kite. Brian May, who put his astrophysics PhD on hold to play guitar in Queen — and then, decades later, went back and finished the doctorate.

None of these people were behind. They were sampling. They were accumulating range. They were becoming M-shaped, often without a word for it. The head start is largely a myth we tell ourselves; the more honest story is that a rich, winding path tends to arrive somewhere more interesting than a straight, narrow one.

So, a good problem to have

Here’s where I’ve landed, and what I’d offer you if the “pick a lane” chorus is ringing in your ears.

The restlessness you feel is not a defect to be managed. It’s a signal — that you’re built for breadth, wired to connect things, suited to exactly the kind of complex, unpredictable, wicked world we actually live in. The work isn’t to amputate your curiosities down to one socially acceptable spike. The work is to go deep enough on a few of them that they become real peaks, and then to consciously connect them.

That’s not indulgence. That’s strategy.

I won’t pretend there’s no cost. Breadth without any depth really is just noise, and the genuine risk for people like us is starting ten things and finishing none. Range is earned by going deep somewhere, more than once — not by skimming everywhere. But that’s a discipline to apply, not a reason to apologise for how you’re made.

So if you’ve ever been quietly ashamed of the long list of things you love, let me reframe it for you one last time: it is far, far better to stand at the meeting point of several worlds than to spend a life perfecting one. You don’t have a focus problem. You have range. And in this century, that’s about the best raw material a person can be handed.

What two or three of your interests have you been treating as separate, and what might happen if you deliberately let them talk to each other?

Parting Shot

Mental model: Inversion.

A lot of advantages can be gained simply by avoiding the standard paths to failure. Instead of asking, “How do I solve this problem?” inversion asks, “What would guarantee failure?” Instead of asking, “How can I achieve this goal?” it asks, “What is preventing me from achieving it?”

The next time you find yourself struggling, ask yourself how you could guarantee failure. The answers may surprise you and open up new avenues for possible solutions.