Writing plans that survive first contact with code
A plan is the difference between 'build the right thing on the first try' and 'redo it three times because nobody wrote down what done looks like.'
A design document says what to build. A writing plan says how to build it, in what order, and how you'll know each piece is done. The gap between those two is where most projects go sideways. Someone starts building, realizes halfway through that step 4 depends on step 2 which hasn't been done yet, and now you're untangling a mess.
A writing plan is a checklist with teeth. Each task says which files change, what the change does, and how to verify it worked. When things break, you know exactly where in the sequence the problem started.
I used writing plans for every major feature on this portfolio. The blog reorganization, the featured-post system, the deploy safety checks. Every time, the plan caught ordering problems I wouldn't have noticed until I was deep into the wrong approach.
Start with a brainstorm or design doc that describes what you want. Then break it into numbered steps. Each step should answer three questions: what changes, why, and how do I know it worked?
The plan goes into a document you can reference as you build. Check off each step as you complete it. If a step turns out to be wrong, update the plan before changing the code. The five minutes you spend writing the plan saves thirty minutes of cleanup.
Anything that touches more than two files or takes more than an hour. The overhead is maybe five minutes. The overhead of cleaning up work that went in the wrong direction is an hour or more. The math is obvious once you've been burned once.
The plan is a contract between you and the work.
Product leader shipping across enterprise SaaS, AI in production, and 0→1. Writing about what actually ships — not what sounds good in a deck.