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by emidln 4500 days ago
Teams I've been a part of are 3/4 (3 successes, 1 failure) on total rewrites over my career. The failure was entirely my fault as a developer not knowing my own limits (coding, design, security, devops, business reqs, managing up can't happen (at least for me) in the same 60 hours a week). It still almost succeeded on strength of the design and ability of my amazing coworkers to aggressively simplify and consolidate all the things.

Rewrites fall into two categories: essential to business and doomed to fail. If it's essential that the business execute on a rewrite, it will happen or the business will fail. If it's not essential, it very well might be the reason the business fails (siphoning away talent and squandering time when a refactor or benign maintenance would suffice). Precisely because massive rewrites are so risky, they are undertaken by the foolish (myself firmly in this camp). The heuristic under which they might succeed is bare necessity.