There's no fool like an old fool.

Why I am terrified of looking stupid.

How many things do I know how to do?

I couldn’t begin to catalog them all. There are so many things I’ve learned in my life.

Some I learned in school, some from reading books, but most I learned by doing, by taking risks, by failing, iterating, and improving my way to expertise.

You’d think that after all that, I’d be fearless. I’m not.

After all, I’ve become an expert, and the world sees me that way too. I don’t appear as a floundering beginner anymore, but as a supremely competent adult who has the answers and is sought out for advice.

Experts don’t like to fail. It undermines our credibility. And we have dignity to maintain as we get older. We can’t look foolish if we want to appear wise.

By the time a man reaches fifty, he’s spent decades building a reputation for competence. Young colleagues stop by his office — or his Slack — to ask how things work. His kids call him when their landlord is being unreasonable or their car makes a noise. Neighbors defer to him on baseball trades and fishing lures and lawn care and anything else he has somehow lived long enough to have an opinion about. He knows how to tip at a restaurant, how to talk to a contractor, how to read a balance sheet. The world has decided he is a person who knows things.

This is not entirely comfortable. Authority carries a certain weight — people expect you to have answers, so you learn to project confidence even when you’re improvising. But it also becomes part of how you see yourself. The identity of the competent man is seductive and hard to shed.

And nothing threatens it quite like being a beginner at something.

I notice this particularly in men — including myself. Women sign up for art classes in droves. About 85% of the students at Sketchbook Skool are women. Conferences, workshops, retreats — same story. I’ve thought a lot about why. The most likely answer is that many men would rather not be seen not knowing something. We will get lost rather than ask for directions. We will assemble furniture without the instructions and spend an extra hour doing it wrong. We will sit in silence at a dinner party while the conversation strays into territory we don’t recognize, rather than ask a question that might reveal our ignorance.

Art class is the ultimate exposure. You show up not knowing how to do something, and then you do it badly, in front of other people. You’re surrounded by strangers who may be better at it than you. There’s no jargon to hide behind, no way to make not-knowing sound like strategy. For a man who has spent decades being the one people come to with questions, that’s not a learning opportunity — that’s an identity crisis with a paintbrush.

When we stop learning, we stop growing, and when we stop growing, we start dying. But to learn, we have to be willing to fail.

A lot of this fear has earlier roots than we think. When we were kids, around fifth grade, the boy who drew better than everyone else was either admired or resented — but either way, everyone else knew where they stood. We absorbed a verdict about ourselves and our abilities, and then filed it away. “Not an art person.” Case closed.

The trouble is, we filed it away in 1979 — or whenever fifth grade was — and never re-examined it. We’ve re-examined almost everything else. Our politics, our diets, our careers, our marriages. But we accepted the art verdict at age ten and have been carrying it around ever since like a library book we forgot to return.

Psychologists talk about two kinds of intelligence — fluid and crystallized. Fluid intelligence is the raw processing power of youth: quick uptake, fast pattern recognition, the ability to absorb new information at speed. That peaks in your twenties and declines slowly from there.

Crystallized intelligence is different. It’s the accumulated weight of experience — knowing not just facts but how things connect, what matters and what doesn’t, when to trust your gut and when to ignore it. And it continues to build well into your seventies and beyond.

So the older you are, the better equipped you are to learn something like art — where so much depends not on dexterity or speed but on seeing, on patience, on the willingness to keep going when a drawing isn’t working. Failure is an option. In fact, it’s essential. You already know that most things worth doing require perseverance. You’ve proven it, many times over, in other parts of your life. You just haven’t applied it here yet.

Something else I read: neuroscience has overturned the old assumption that adult brains can’t grow new cells. They can, and they do — particularly when we engage in creative activity. The brain changes shape depending on how you use it. Drawing, painting, making anything by hand — these activities build new neural pathways, keep the mind supple, and give it something genuinely novel to chew on.

In short, taking up art at sixty is one of the better things you can do for the organ in your skull.

But forget the science for a moment. The real point is this: the older we get, the more we get out of art.

When you’re young and busy, you draw, and what you produce feels thin, hurried, an afternoon’s entertainment to impress your friends by drawing a rock star or a comic book superhero. When you’re older, and you sit down with a sketchbook and actually look — at the coffee cup, the street, the face of someone you love — you start to see what you have. The years accumulate in what you notice. The things you’ve learned to pay attention to show up on the sketchbook page. And you’re not doing it just to get a grade or meet a deadline, but to gain the quiet, private satisfaction of having made something true to you.

To start, you don’t need a class, just a pen and something to draw on.

But if a class helps you get started — if seeing other beginners fumble alongside you makes the fumbling easier — then take one. The people in the class are not there to judge you. They’re there because they’re in exactly the same boat, a little nervous, a little hopeful, wondering whether they can do this.

Most of them can. So can you.

Your pal,

Danny

P.S. It took me twelve years to finally finish my latest video. Back in 2014, Jenny and I drove from Los Angeles to New York City — 3,717 miles, ten days — and I drew and watercolored the entire trip as we went. The footage and the journals sat on a hard drive ever since. Last week, I finally put it all together. Click to watch it on YouTube