Structure is great for giving people things to focus on and to channel their creative energy through.

Structure is bad for constraining people and sucking away their motivation.

It’s easy to either become too rigid with your structure, or to embody a swirl of chaotic energy. You need to know when to do what.

One way to do this is to find a common definition of success. Cal Newport writes, “When deciding to embrace a self-motivated ambition, choose a definition of success that your aunt in Peoria would understand and find impressive. This is not about succumbing to the status quo, but instead setting yourself up to receive the brutal but useful feedback needed to eventually start producing things too good to be ignored.” 

I really appreciate Shea Serrano’s interview with Michael Gervais on Finding Mastery, because his approach to writing is so matter-of-fact. There was no grand plan; Serrano and his wife Larami were expecting twins, and they needed to make more money. 

The goal was simple: Shea Serrano needed to make an extra $400 per month. He was looking at the grocery stores, at Target, and at waitering jobs at restaurants, but none of them would hire him because he was working full-time as a teacher. He googled work from home jobs, and found that writing was one of them, and he started doing that. 

He cold emailed a bunch of people, found a woman and man who would pay him $15 to write about the Texans for their small neighborhood publication, the Near Northwest Banner. He took those pieces to the Houston Press, and connected with an editor there, and then start pitching LA Weekly and the Village Voice. Once he was published in those, he went to MTV, Rolling Stone, and ESPN. 

Serrano says, “Things just kept happening in that path. Like one little thing each time. That’s literally how you climb a ladder, is fucking one rung at a time. You don’t fucking go from the bottom straight to the top.” (See also taking the stairs, and not waiting for the elevator.)

It was a very unremarkable start to what has become an incredibly successful writing career. (In addition to his NYT bestsellers, Serrano sells books independently! He’s still walking both paths.)

I really like Nathan Barry’s ladder to wealth creation.