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Never Rewrite: Software Engineering & AI Coding

Isaac Askew and Jeffrey Sherman

‘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 rewrite, a port to a new language, or despair that their code is unfixable.

It’s not unfixable, and we explore how to get started along with an array of other software topics in our eponymous podcast.

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179 atal

  1. AI & Eternal Software Projects (Ep. 179) 17:40
  2. Cancel All Your Meetings, AI Edition (Ep. 178) 18:49
  3. The SaaSpocalypse Is Here (Ep. 177) 30:10
  4. Revisiting 'Out of the Crisis' (Ep. 176) 16:12
  5. Revisiting 'The Goal: A Process of Ongoing Improvement' (Ep. 175) 16:31
  6. The Rise of Personal AI Assistants (Ep. 174) 27:57
  7. How My Workflow Is Impacted by AI (Ep. 173) 23:33
  8. AI-Monitored Release Processes: A Log Anomaly Checker (Ep. 172) 10:06
  9. Using AI to Complete a Half-Finished Rewrite, Part 2 (Ep. 171) 29:24
  10. Refactoring: What Changes (And Doesn't) in the Age of AI ft. Ravi Ram (Ep. 170) 34:20
  11. Using AI to Complete a Half-Finished Rewrite (Ep. 169) 19:44
  12. Are AI-Driven Pull Requests Too Large? (Ep. 168) 21:37
  13. AI & WIP Fundamentals (Ep. 167) 25:27
  14. Solutioning in the Age of AI (Ep. 166) 17:54
  15. AI & The Age of Transient Apps (Ep. 165) 18:29
  16. AI Horror Stories (Ep. 164) 21:40
  17. Can AI Tell You What Your Goals Are? (Ep. 163) 20:12
  18. Terminology: Rewrite, Refactor, Rebuild, Redo? (Ep. 162) 12:17
  19. You Can't Vibe Code Reputation (Ep. 161) 22:54
  20. TheseusShipping Outside of the Tech Stack (Ep. 160) 20:51
  21. Vibe Coding (Ep. 159) 18:49
  22. Token-Based Billing Is Nuts (Ep. 158) 26:42
  23. Episode 157: Is AI Making You The New John Henry? 23:13
  24. Episode 156: Modernization: Where AI Doesn't Save You Any Steps 9:43
  25. Episode 155: Agentic Development Is Turning Engineers Into Product Owners 21:12
  26. Episode 154: Feature Parity Pitfalls 12:20
  27. Episode 153: The Rewrite Trap & Sunk Cost Fallacy 19:12
  28. Episode 152: The Moving House Metaphor for Software Rewrites: How AI Changes the Game 16:40
  29. Episode 151: Celebrating Wins During Constant Iteration 11:37
  30. Episode 150: The AI Rewrite Trap 31:37
  31. Episode 149: Isaac Does a Rewrite? 49:23
  32. Episode 148: How Human Taste Shapes the Future of AI and Coding 35:26
  33. Episode 147: Managing Organizational Change ft. Sophia Rosa 38:24
  34. Episode 146: How AI is Reshaping Careers and Workflows 27:46
  35. Episode 145: Outdated Programming Techniques: Browser Compatibility 6:36
  36. Episode 144: Outdated Programming Techniques: Bit Masking 6:32
  37. Episode 143: Tactics to Obscure (Parody) 10:47
  38. Episode 142: Are You Ready to Scale? A Local Case Study 23:50
  39. Episode 141: How Rewrites Create Accountability Black Holes 14:13
  40. Episode 140: Evolving Past Boomer AI 35:22
  41. Episode 139: Rewrites - A Failure of the Imagination ft. Mark Mandau 34:12
  42. Episode 138: The MVP Worked. Do We Rewrite It To Scale? 20:50
  43. Episode 137: 2025 Year in Review 22:31
  44. Episode 136: Key Questions to Ask When Navigating Your Career 14:13
  45. Episode 135: Is Changing an ERP System a Rewrite? ft. Sophia Rosa 49:56
  46. Episode 134: A Stream of Consciousness Chat on AI, Tech, & Layoffs 24:15
  47. Episode 133: The Consequences of Having Multiple Sources of Truth 15:22
  48. Episode 132: A Thankful Thanksgiving Episode 7:28
  49. Episode 131: Rewrites from a Product Perspective ft. Mark Mandau 50:50
  50. Episode 130: The Pains Caused by Differing Abstractions Pt. 2 - Real World Examples 23:00