2025-05-27 · Technical Discussion

Lessons from rewriting instead of refactoring

A postmortem where the rewrite was right, and the two places it nearly was not.

Introduction

Incremental refactoring is sound advice until the module boundary itself is wrong. We revisit a two-quarter migration, what we preserved, and the warnings we ignored on the way.

Small things that compounded

Looking back over Technical Discussion work, the wins were unglamorous: a naming fix, a deleted config, a checklist nobody has had to edit since.

What made them stick

  • They were owned by one person, not a committee.
  • They shipped with a way to notice when they stopped working.
  • They removed a decision instead of documenting one.

Steal this

Pick the irritation you have mentioned three times this month. That is your next project — it has already proven its staying power.

Closing

Big rewrites make better stories; small compounding makes better systems.