Software Rewrites

Episodes about the rewrite itself: why teams reach for one, what happens when they do, and how the ones who escape got out.

A rewrite is a bet that you can rebuild a working system while the business, its customers and its competitors all keep moving. Most of these conversations are with people who took that bet. The recurring shape: six months becomes two years, feature parity stays just out of reach, and the original system is still in production when the project gets canceled. A few episodes cover the other ending, where someone called it off early and salvaged the work.

If you are weighing a rewrite right now, start with the full guide, or the shorter pieces on the big rewrite and what the successful ones did differently.

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