To succeed as a creator, don’t “roll the dice”—get dealt another hand

The more creative work you produce, the better your chances of making a masterpiece.

Consider that Picasso painted more than 1,800 paintings, Bach wrote over 1,000 pieces, and Beethoven, 650.

It makes sense. If each piece has a one in one-hundred chance of being a masterpiece, naturally, the more pieces you produce, the better your chances you’ll have a hit.

But it’s not merely a matter of chance. It’s also a matter of skill.


I often use the analogy of “rolling the dice” to stress the importance of producing a large volume of creative work.

But when I used this analogy in my podcast conversation with Adam Conover, creator of Adam Ruins Everything, he stopped me.

Adam Conover of “Adam Ruins Everything”

“I think of that process as more like building,” he said. “It’s not like I’m hoping every time I’m going to get a hit.”

Adam told me about how—after his successful sketch group broke up—he started back at square one, trying to succeed in comedy. He spent five years going to open mics in New York.

“Even the bad sets are worth something,” he said. “I don’t think it’s a gamble to go do those things.” He acknowledged how luck played a part in his success, but ultimately, he said, “I think it’s just going out and doing the work.”


I have a friend who is a professional Poker player. He spends each day playing poker online for eight hours.

Sometimes he has a bad day. Sometimes he has a good day. Sometimes he has a terrible day. Other times, he has a fantastic day.

But, it’s a job. Even if he has a long losing streak, he knows that—at his skill level—if he keeps it up, he’ll make about $100 an hour.


Craps, where you “roll the dice,” is widely considered a game of chance. You can learn some basic strategy, but the house still has an edge—otherwise they would go out of business.

Poker, however, is widely considered a game of skill. If you learn strategy and the mental game, you can make a living playing poker. The house earns on each hand whether you win or lose.

Like in creative work, in Poker, sometimes you get lucky. Maybe one of the greatest songs ever comes to you while you’re sleeping. Maybe you get dealt a royal flush.


But skill matters, too. Even if you get lucky at the start, if you keep playing poker without building up skill, you will run out of money. If you keep doing creative work without building up skill, you will run out of time.

How do you build up that skill? Adam Conover suggests, “focus on: What can you be doing every day to make yourself better?” For him, that was simply walking out the door, and going to open mics. For me, that’s writing each day, and putting my work out there to get feedback.


Finding success in creative work does have an element of chance. In some ways, you really are “rolling the dice.” You have to play to ever hope for a lucky break. But each time you play, you’re learning. So don’t just roll the dice. Get dealt a new hand. Sometimes, you get the signals that you should play the hand, or even up the ante.

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