I have a good friend who is intelligent in many ways, but bad at planning / achieving his goals / being medium+ agency. He's very habit and routine driven, which means his baseline quality of life is high but he's bad at, e.g, breakdown an abstract and complex problem statement like "get a job that pays +100K and has more interesting co-workers" into a series of concrete steps like {figure out what the meta-game is in job hunting, find the best jobs, learn skills that are optimized for getting the type of job you want, etc.}

We have mutually agreed he'd like to get better at this skill, and so I'm trying to help him out.

Are there good books / practices / coaches / literally anything he can do to improve this skill? A simple and obvious thing would be for him to make a bunch of [...]

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First published:
June 9th, 2025

Source:
https://www.lesswrong.com/posts/fCvxSAnmYqEKBMaoB/how-to-help-friend-who-needs-to-get-better-at-planning

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Narrated by TYPE III AUDIO.