Why Planning More Was Making Me Less Productive

I went back through three months of my own planning documents recently and found something I didn't want to find: the plans had gotten more detailed every month, and the amount of real, shipped work had gone down over the same period.

Planning as a disguise

Planning feels like progress. It has the shape of work — you're thinking about the task, structuring it, breaking it down. But past a certain point of detail, it becomes a very comfortable way to interact with a project without doing the part that's actually hard: the ambiguous, uncertain, possibly-wrong first attempt.

I was over-planning specifically the projects I was most nervous about. That's not a coincidence.

What I changed

I gave myself a planning budget — roughly ten minutes per task, hard stop — before requiring a first attempt, however rough. Not a perfect plan followed by execution. A rough plan, immediately tested against reality, refined from there.

What happened

More shipped work in the following month than in the prior three combined. Some of it was worse for having less planning behind it. Most of it existing at all was worth more than the marginal polish I would have added with more upfront planning.

I don't think planning is bad. I think planning past the point of reducing real uncertainty is just a more socially acceptable form of procrastination, and it took embarrassingly long to see that in my own habits.