TL; DR:

• Software rewrites are almost ALWAYS underestimated
• The "all or nothing" approach is the most dangerous trap
• The Strangler Fig pattern lets you rewrite incrementally and safely
• Join me for the live stream (or watch the recording) on Monday, February 9th at 7:00 PM Pacific!

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Why Do Software Rewrites ALWAYS Take Longer Than Expected?

I saw a post on the ExperiencedDevs subreddit that really resonated with me. Someone pointed out that after about 8 years in the industry, every single rewrite they've seen has taken significantly longer than teams planned for. And for some reason, people always act surprised.

Spoiler alert: that's also been my experience.

And I'm not talking about being a little bit off. I'm talking about -- if someone tells me "it's going to take us X amount of time to rewrite this," I would at least double it. If they say a year, I'm saying two years. At least. That's just based on my own lived experience with various rewrites across my career.

Now, my goal here isn't to say "a rewrite is the devil, never do it, never consider it." It's just that I think a lot of the time, rewrites are approached as this silver bullet solution for all the problems we have -- and the amount of time and complexity to pull it off gets grossly underestimated. You can check out my full thoughts on this in the video below: