If you can fail on purpose Michael Mauboussin writes in The Success Equation, then the endeavor is skillful. It’s easy to purposefully lose a game of h-o-r-s-e.
Noam Dworman expands this idea some. Talking about comedians who come through his Comedy Cellar he told Tyler Cowen:
Now, there’s a lot of overachievers in this profession. It’s not like the NBA. If you want to be in the NBA, you’ve got to be in the top one-tenth of basketball players in the country, or it’s immediately obvious.
You can scratch out and work hard and put together a good 15 minutes, so there are a lot of overachievers working in comedy. The real super talent, the real gems, like the Chappelles, like the Louis C.K.s — they really are on another level, and the world sees that.
https://conversationswithtyler.com/episodes/noam-dworman/
What makes a great comedian, Noam expanded, was someone who was funny but also needed to be on stage. They were compelled. Drew Carey simply got a book from the library and then wrote a joke a day. It had to be clean, original, and no knock-knock-jokes. Carey could – and did – write those jokes they just didn’t count. And he assembled fifteen minutes, then a set, then a career.
Mauboussin mostly writes about sports and investing because those domains are measured.
But it’s helpful to color in some other areas of the system. To think about what’s luck, what’s skill, and how they matter.