A note on forcing functions, inspired by my wife’s post:

My Substack started taking off (in relative terms, years ago) when I committed to writing 30 posts in 30 days. This was back when Ship30for30 was big, that cohort-based course where people wrote 250 word essays. I was like: “no, that is for cowards. I will write 30 actual posts, like, between 500 and 2000 words.” As Cate’s post suggests doing, I kept myself accountable via a commitment mechanism, pledging to donate $2000 to the communist party of Canada if I failed.

It was one of the most emotionally abrasive months of my life. At that time, I was a pretty perfectionistic writer, dedicated to making every sentence memorable. But this was not an option during the 30-day interval, given how much I was writing. Every day, I published something that felt awful by my standards — I was constantly pale with embarrassment and terrified that I’d run out of ideas. Many writing days I literally shook as I beheld whatever came through my fingers.

My subscriber count doubled and nobody seemed to notice that I was writing badly. It went so well actually did it twice more — the second run also felt awful, but less so. I half-bailed out partway during the third attempt, but I don’t feel so awful about this in retrospect; it was still a pretty good run!

The experience completely changed the way I think about creativity, especially from an emotional perspective. My relationship with embarrassment changed totally — I started experiencing it as “the feeling of breaking my inner ruleset,” rather than “a definite sign that something has gone wrong or will go wrong.” I started liking fear, also. Since then, I’ve continuously tried to move towards embarrassment and fear in many facets of my life, and I’m always trying to break my own rules.

It also changed the way I structure my working life, creative and otherwise. Previously, I was scared whenever I didn’t have a way out of a project, and tried to aim for deadlines that allowed me time to dawdle. But now, I habitually make sure the exits are blocked on major projects — I try to assign myself slightly unreasonable deadlines, and try to make it personally costly to miss them. 80% of the time, it works 100% of the time, and every time I learn something about my capacity.