The Rewrite Trap by Jeffrey Sherman and Isaac Askew — book cover Sale

(Preorder) The Rewrite Trap Why Software Rewrites Fail and What To Do Instead

A practical guide for startup engineers and leaders who want to fix software, not rebuild it from scratch.

What you'll learn:

  • How to identify when a rewrite is risky
  • How to incrementally modernize systems
  • Case studies from real companies
  • The "TheeSeeShip" approach

Preorder today and get:

  • Early draft chapters
  • Exclusive Q&A session with the authors
  • Your name in the acknowledgements

$25.00$39.00

Preorder the book

‘Never Rewrite’ is a mantra of ours in the programming realm. Often times when software developers encounter nightmare codebases, the thought crosses their mind to work towards a complete rewrite.

Don’t do that.

We explore what to do instead along with an array of other software topics in our eponymous podcast.

Listen & subscribe

Rated 5.0 on Apple Podcasts & Spotify

About the podcast

Never Rewrite is a weekly software engineering podcast for developers and engineering leaders. Jeffrey Sherman and Isaac Askew dig into the real decisions behind shipping and maintaining software — when to modernize instead of rewrite, how AI and agentic coding tools are changing the craft, scaling, team standards, and engineering careers. Browse every episode on the episodes page.

What is the Never Rewrite podcast about?
Never Rewrite is a software engineering podcast hosted by Jeffrey Sherman and Isaac Askew. Each episode is a candid conversation about why complete software rewrites fail, how to modernize legacy code instead, and how AI and agentic coding tools are changing the day-to-day work of building software.
Is Never Rewrite a coding podcast?
Yes. It's a coding and software engineering podcast for working developers and engineering leaders. Topics range from legacy systems and incremental modernization to AI-assisted development, scaling, team standards, and engineering careers.
Who should listen?
Software developers, engineering managers, CTOs, and startup founders who would rather fix and evolve their software than rebuild it from scratch.
How often do new episodes come out?
New episodes are released weekly, with more than 150 episodes already in the archive.
Where can I listen to Never Rewrite?
Never Rewrite is available on Apple Podcasts, Spotify, Amazon Music, and YouTube. You can also browse every episode on neverrewrite.com.