I had this nice fantasy when I published my second book that I would then churn out a nice essay every week. If I had done that, I would have over 50 essays out now. But I haven’t. So something was wrong about my model of myself. What was wrong exactly? Mm I have another draft here called Incorrect Estimates, maybe I’ll merge it

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My estimation ability has always been something like… a clown, an oracle and an unflinching optimist in a trenchcoat. There are also some dissenting voices in there – a cynic, a pessimist, a worrywart, but they typically have much less sway when it comes to most things. They have more power when it comes to doing things with potential downside. But when it comes to things with potential upside, I can be a manic hype machine.

It’s not something I’m proud of, and if I think about it a little more, it’s something I’ve long been averse to really properly examining. I’m sure I’ve tried several times over the years; I can probably find some old writing about it, but I don’t feel like looking it up right now. Rather I’m in the mood to think through things from scratch again.

There are three big things that come to mind. Maybe four? Let me just list out all the things:

• my homework, when I was a student
• my work-work, when I was an employee – and even recently
• my estimation of my 1000wordvomits writing project
• my ebook Introspect, which took I think about 2 years longer than I expected
• every time i sit down to write a substack essay

Almost every other day or so, I get some clarity in the shower, and then I eagerly storm into my study and announce to my wife, “I think I’m going to publish an essay today!” And the long-suffering woman smiles and laughs, with the knowledge that I have only published about 7 times out of 100, and it was maybe 2 out of those 7 times that I wrote something from start to finish and hit publish within a few hours.

I first started 1000wordvomits in December 2012. I excitedly thought to myself that if I published just 1 a day, by writing feverishly for 15 minutes without editing, that it would take me just 1,000 days to finish the whole project. That would have been in July 2015. At the end of July 2015, I had written 0435/1000 wordvomits. Alright, not too great, but not entirely terrible either. I was almost halfway done. Maybe I should’ve planned to take breaks or something. Also, when I had started the project, I hadn’t gotten a job yet, so I was thinking like an unemployed person. Once I got a job, I was much busier, and much more tired. So… if we did 435 in 1000 days, the math would suggest that… we’d get to 870 in the next 1000? Wrong. Another 1000 days later we get to May 2018, a month in which I only wrote one single wordvomit.