Creative Company · Musing 001 · Inspiration AUGUST 27, 2026 · 12 min

Maybe you're right. Luck is what it takes.

There are four kinds of luck, and only one of them is out of your control.

Guido Reni, Abduction of Helen, after 1627. Art Institute of Chicago, public domain.
Guido Reni, Abduction of Helen, after 1627. Art Institute of Chicago, public domain.

Maybe the artists you watch pulling ahead of you got a break that hasn’t come your way yet. And maybe you’ve been carrying a suspicion you’d never say out loud, that skills and hard work aren’t actually the whole story, and something else decides who makes it.

As heretical as it sounds, I would agree.

The thing is though, there are actually four kinds of luck, and only one of them is out of your control.

I stumbled onto this idea over the weekend and I haven’t been able to put it down since. It’s almost fifty years old and it came out of medical research, of all places, which is probably why nobody has ever handed it to an artist. Somewhere in the middle of reading it I realized I wasn’t reading about scientists at all, I was reading about you (and me), and I felt called to write this.

Here are all four. Three of them belong to you.

The first kind: blind luck

This is what everybody means when they say the word. The collector who wanders into the right room on the right afternoon. Being born in a city that has galleries in it, or to parents who bought you paint instead of telling you to pick something sensible.

It’s real, it matters, and there is not one thing you can do about it. This luck is completely out of your control.

Almost every artist I’ve ever met has built their entire plan around this one. Get discovered. Get seen. Get picked. Elli traces it straight back to the movies: “We see a lot of movies about people getting discovered, a lucky break, whether that’s a musician or an actress or a writer or an artist. And there aren’t any movies about the hard work.”

So of course we all grew up believing the break is the story. Fine, keep it. It’s one out of four.

Raphael, Guard Drawing His Sword. Art Institute of Chicago, public domain.
Raphael, Guard Drawing His Sword. Art Institute of Chicago, public domain.

The second kind: luck from motion

Charles Kettering said it plainly: “I have never heard of anyone stumbling on something sitting down.”

Luck can only find you where you actually are, so what matters is how much surface area you’ve built for it to land on. Paintings finished, not started. Calls for art entered. The show you almost skipped and drove to anyway. The email you sent to the woman who bought a piece from you two years ago, just to tell her what you’re painting now.

This is similar to the concept that inspiration finds you working.

Elli said this in an interview a few weeks ago and I keep coming back to it:

You have complete authority and power to decide how long you stick to something, how much you push, how hard you work, how many hours you put in, how many paintings you paint, how much promoting, how many places you put it out there, how many people you contact, what business models you try, what art shows you try. You’re in charge of all of that.

YOU are in control of how much work you put in, and therefore, how much motion-luck you have.

Andrea Mantegna, Four Women Dancing, about 1497. Art Institute of Chicago, public domain.
Andrea Mantegna, Four Women Dancing, about 1497. Art Institute of Chicago, public domain.

The third kind: luck from preparation

Luck can sometimes arrive looking like a request. A woman asks whether you could do something like that one but bigger, and in blue, in the next few weeks. A gallery says they’d take you if you had six pieces that hang together, oh and “we want to do a show next month or we might have to wait until next year.” A designer wants three for a lobby and needs to see them next week.

That’s what your skills are for. That’s what the drawing section is for, and the value studies, and that alla prima still life where you’re mixing every color you need out of only six tubes. Nobody tells you that the lesson you keep pushing to tomorrow is a luck machine, but that’s exactly what it is. Skill is the difference between an opportunity you’re ready for and a story about the opportunity you had to turn down.

Make your own preparation-luck.

Raphael, Upraised Right Hand, 1518-20. Art Institute of Chicago, public domain.
Raphael, Upraised Right Hand, 1518-20. Art Institute of Chicago, public domain.

The fourth kind: luck that comes looking for you

This one is honestly weird, but I think it’s my favorite.

There’s an example I love about a deep-sea diver. Become the best deep-sea diver alive, and when treasure hunters find a shipwreck there’s only one person for the job. Nobody handed him anything. He spent years becoming the ONLY person worth calling, and then the call came.

For an artist, that’s your voice.

A painter whose art looks like everybody else’s literally can’t be sought out, and that has nothing to do with how skilled they are. Very few people wake up wanting just another “good painter.” They want a specific feeling on their wall. That color, that light, that particular stillness or motion or hope or joy or melancholy. When five of your paintings look like one person made them, you become the answer to a question somebody out there is already asking. You tap into an already existing desire that a specific group of people hold.

Finding your voice is the part where you become findable. Not waiting-to-be-discovered findable. But the only person who captures that kind of feeling so you’re recommended as the “artist who does ______” in conversation. This takes work.

Why I wanted to write this to you

Elli said something to me a couple weeks ago that’s been rattling around in my head ever since:

Nobody wants to be responsible. Nobody wants to be accountable. If it’s got to be about luck, who you know, a silver bullet, then you’re not responsible. You’re not the one that’s in charge. But what we teach is that you are empowered because you are responsible, and that’s a good thing.

Waiting to be discovered feels like humility, and it’s honestly the most comfortable seat in the house, because as long as the whole thing is a lottery then nothing that happens next is on you. You can absolutely sit there. Blind luck does occasionally show up for people who did nothing to earn it.

Or you can go get the other three.

Three of the four kinds of luck are decisions. If you have already spent years on this, you have been making them without calling them that.

Nicolas Poussin, Birth of Alexander, 1640s. Art Institute of Chicago, public domain.
Nicolas Poussin, Birth of Alexander, 1640s. Art Institute of Chicago, public domain.

One more quick story

Years ago my Bubbi (grandma) was at a friend’s house and saw a small abstract painting sitting in a back room. Something about it pulled her across the room. She insisted on knowing who the artists were. The friend didn’t want to share because she was a designer and secretive about her sources. Finally, after annoying persistence from Bubbi, the friend relented. Then Bubbi bought a painting that changed her life. She got on the artists’ email list, became friends with the family, and eventually she invited them out to her house in Flagstaff.

And when I was 17, I met those artists’ daughter, Dimitra Milan (now Dunn).

Blind luck for me. Completely.

I owe my marriage and what Milan Art Institute is today to my Bubbi walking past a painting in somebody-I’ve-never-met’s back room. I mean, at a certain point, we have to stop calling it luck, right? At a certain point, someone has to say the thing that feels almost weird to admit.

Destiny.

But look at what had to be true before Bubbi ever walked in that room. Somebody stretched that canvas. Somebody mixed those colors and finished it and let it leave the studio on an ordinary day when nothing was riding on it and nobody was watching. And I mean c’mon, think about everything leading up to that one small painting: the years Elli and John spent learning to paint, the paintings that didn’t sell, but the decision to keep making them anyway.

Blind luck can’t land on a painting that doesn’t exist yet.

So paint the thing. Finish the section you’re stuck in. Enter the call for art with the piece you’re not sure about. Send the email. Put five of your paintings side by side and find out whether they look like one artist made them yet, and if they don’t, keep going, because that’s the tough part where (sadly) lots of people stop.

Stay in motion. Get prepared. Become the kind of artist that luck comes looking for.

Do that long enough and somebody will snarkily call it a lucky break.

But you’ll know better.

You might even start to suspect it was destiny the whole time.

You’re not crazy for wanting this. You never were.

Rooting for you,

Jake

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