The archive
Issue #008
Codebase Horror Stories 8 min read· 25 Jul 2026

The Rewrite Gambit

Two years of microservices. Millions of lines of code. Dozens of tables. A former CTO who walked out. And a CEO who needed it to work for properties. The story of how I bet everything on a 3-month rewrite.

Share
CTO takeaway

The lesson, minus the scar tissue.

  • Never confuse complexity with sophistication. A simple, working system beats a complex, broken one every time.
  • When inheriting a codebase, don't be afraid to call a spade a spade. Two years of work doesn't mean two years of good work.
  • Microservices are a tax, not a prize. Only pay it when you actually need the scale.
  • The best way to convince leadership to rewrite is to show them how much faster they'll ship features. Talk in business terms, not tech terms.
  • A 3-month rewrite is a gamble. But sometimes gambling on simplicity is safer than betting on a sinking ship.
Never miss an issue

Get the next Chronicle in your inbox.

A comic, a story and a takeaway every other week. Written for founders who inherited a codebase they didn't choose.

Free forever. Unsubscribe in one click.

Related Chronicles.