Never Rewrite: Software Engineering & AI Coding
By Isaac Askew and Jeffrey Sherman
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Image by Isaac Askew and Jeffrey Sherman
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Subscribers: 3
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Episodes: 160
Description
‘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.
| Episode | Date |
|---|---|
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TheseusShipping Outside of the Tech Stack (Ep. 160)
|
Jun 19, 2026 |
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Vibe Coding (Ep. 159)
|
Jun 12, 2026 |
|
Token-Based Billing Is Nuts (Ep. 158)
|
Jun 05, 2026 |
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Episode 157: Is AI Making You The New John Henry?
|
May 29, 2026 |
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Episode 156: Modernization: Where AI Doesn't Save You Any Steps
|
May 22, 2026 |
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Episode 155: Agentic Development Is Turning Engineers Into Product Owners
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May 15, 2026 |
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Episode 154: Feature Parity Pitfalls
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May 10, 2026 |
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Episode 153: The Rewrite Trap & Sunk Cost Fallacy
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Apr 24, 2026 |
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Episode 152: The Moving House Metaphor for Software Rewrites: How AI Changes the Game
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Apr 17, 2026 |
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Episode 151: Celebrating Wins During Constant Iteration
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Apr 10, 2026 |
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Episode 150: The AI Rewrite Trap
|
Apr 03, 2026 |
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Episode 149: Isaac Does a Rewrite?
|
Mar 27, 2026 |
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Episode 148: How Human Taste Shapes the Future of AI and Coding
|
Mar 20, 2026 |
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Episode 147: Managing Organizational Change ft. Sophia Rosa
|
Mar 13, 2026 |
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Episode 146: How AI is Reshaping Careers and Workflows
|
Mar 06, 2026 |
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Episode 145: Outdated Programming Techniques: Browser Compatibility
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Feb 27, 2026 |
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Episode 144: Outdated Programming Techniques: Bit Masking
|
Feb 20, 2026 |
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Episode 143: Tactics to Obscure (Parody)
|
Feb 13, 2026 |
|
Episode 142: Are You Ready to Scale? A Local Case Study
|
Feb 06, 2026 |
|
Episode 141: How Rewrites Create Accountability Black Holes
|
Jan 30, 2026 |
|
Episode 140: Evolving Past Boomer AI
|
Jan 23, 2026 |
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Episode 139: Rewrites - A Failure of the Imagination ft. Mark Mandau
|
Jan 16, 2026 |
|
Episode 138: The MVP Worked. Do We Rewrite It To Scale?
|
Jan 09, 2026 |
|
Episode 137: 2025 Year in Review
|
Jan 02, 2026 |
|
Episode 136: Key Questions to Ask When Navigating Your Career
|
Dec 26, 2025 |
|
Episode 135: Is Changing an ERP System a Rewrite? ft. Sophia Rosa
|
Dec 19, 2025 |
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Episode 134: A Stream of Consciousness Chat on AI, Tech, & Layoffs
|
Dec 12, 2025 |
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Episode 133: The Consequences of Having Multiple Sources of Truth
|
Dec 05, 2025 |
|
Episode 132: A Thankful Thanksgiving Episode
|
Nov 28, 2025 |
|
Episode 131: Rewrites from a Product Perspective ft. Mark Mandau
|
Nov 21, 2025 |
|
Episode 130: The Pains Caused by Differing Abstractions Pt. 2 - Real World Examples
|
Nov 14, 2025 |
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Episode 129: Credit Where Credit Is Due
|
Nov 07, 2025 |
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Episode 128: Revisiting An Old Story With Our Current Experience
|
Oct 31, 2025 |
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Episode 127: The Pains Caused by Differing Abstractions
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Oct 24, 2025 |
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Episode 126: Does Iterative Replacement Trap You In Legacy Frameworks?
|
Oct 17, 2025 |
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Episode 125: Navigating Risky Software Setups
|
Oct 10, 2025 |
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Episode 124: Treating Communication Gaps Like Tech Debt ft. Austen Tucker
|
Oct 03, 2025 |
|
Episode 123: Is Switching Jobs a Career 'Rewrite'?
|
Sep 26, 2025 |
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Episode 122: Providing Constructive Feedback
|
Sep 19, 2025 |
|
Episode 121: A Helpful Analogy For Understanding Legacy Code & Tech Debt
|
Sep 12, 2025 |
|
Episode 120: Bad Testing & Release Practices Are Cultural Problems, Not Technical Problems
|
Sep 05, 2025 |
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Episode 119: Iterating, Adapting, & Pivoting ft. Day Martin
|
Aug 29, 2025 |
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Episode 118: Recovering Value From Failed Projects
|
Aug 22, 2025 |
|
Episode 117: How to Make Incremental Changes Visible
|
Aug 15, 2025 |
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Episode 116: Inverting the Testing Pyramid Pt. 2
|
Aug 08, 2025 |
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Episode 115: [CI/CD] Beautiful Feedback Loops with guest Spriha Tucker
|
Aug 01, 2025 |
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Episode 114: Old Projects Never Die, They Just Fade Away
|
Jul 25, 2025 |
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Episode 113: Do You Want a Better Version of What You Have?
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Jul 18, 2025 |
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Episode 112: The Impact & Cost of Hidden Business Rules
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Jul 11, 2025 |
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Episode 111: The Social Aspects of a Failed Rewrite
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Jul 04, 2025 |
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Episode 110: MVPs, YAGNI, and the Goldilocks Problem
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Jun 27, 2025 |
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Episode 109: Conway's Law and Software Quality
|
Jun 20, 2025 |
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Episode 108: Consolidating Tech Stacks - Is It Worth It?
|
Jun 13, 2025 |
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Episode 107: Rebuilding vs. Rewriting vs. Refactoring?
|
Jun 06, 2025 |
|
Episode 106: How to Stop a Rewrite in Progress
|
May 30, 2025 |
|
Episode 105: A Core Engine Rewrite with Nick Gerace
|
May 23, 2025 |
|
Episode 104: An Infrastructure Rewrite Story with Guest Paul Stack
|
May 16, 2025 |
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Episode 103: Recognizing When a Rewrite is Failing
|
May 09, 2025 |
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Episode 102: Rewrite Stories with Guest Nick Stinemates
|
May 02, 2025 |
|
Episode 101: Relief vs. Cure
|
Apr 25, 2025 |
|
Episode 100: Detecting B.S. as a Non-Technical Founder
|
Apr 18, 2025 |
|
Episode 99: DOGE Pt. 2: Government Rewrites with Guest Dan Hon
|
Apr 11, 2025 |
|
Episode 98: DOGE's Social Security Rewrite - Killing Americans to Save Money
|
Apr 04, 2025 |
|
Episode 97: Fulfilling Friday - A Tattoo Scam?
|
Mar 28, 2025 |
|
Episode 96: Inverting the Testing Pyramid - Testing Infrastructure Changes ft. Rob Gonnella
|
Mar 21, 2025 |
|
Episode 95: We're Writing a Book!
|
Mar 14, 2025 |
|
Episode 94: What Did You Think You Were Saying Yes To?
|
Mar 07, 2025 |
|
Episode 93: How to Put Work Down When Priorities Change
|
Feb 28, 2025 |
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Episode 92: A Framework for Prioritizing Tech Debt ft. Dustin Rea
|
Feb 21, 2025 |
|
Episode 91: Pushing Pain to Users
|
Feb 14, 2025 |
|
Episode 90: The Hero and the Lifeguard
|
Feb 07, 2025 |
|
Episode 89: How Sonos Lost $500 Million Attempting a Rewrite
|
Jan 31, 2025 |
|
Episode 88: Creating a Culture of Continuous Improvement with Guest Erik Enge
|
Jan 24, 2025 |
|
Episode 87: 2025 Update - State of AI Programming
|
Jan 17, 2025 |
|
Episode 86: Annual Reminder - Prune Your Meetings
|
Jan 10, 2025 |
|
Episode 85: 2024 Year In Review
|
Jan 03, 2025 |
|
Episode 84: The Impact of AI on Interviewing
|
Dec 27, 2024 |
|
Episode 83: The Impact of AI on Recruiting
|
Dec 20, 2024 |
|
Episode 82: Can You Like Tests And Also Believe You're Faster Without Them?
|
Dec 13, 2024 |
|
Episode 81: The Pause
|
Dec 06, 2024 |
|
Episode 80: What is "De-Risking"?
|
Nov 29, 2024 |
|
Episode 79: The Toxicity of "Certainty"
|
Nov 22, 2024 |
|
Episode 78: Is Frontend Modernization a Valid Reason for Rewriting?
|
Nov 15, 2024 |
|
Episode 77: Who Gets To Define 'Shit' Code?
|
Nov 08, 2024 |
|
Episode 76: Aligning Your Company Standards to its Lifecycle Phase
|
Nov 01, 2024 |
|
Episode 75: Rewriting is Gambling - A Lesson in Risk
|
Oct 25, 2024 |
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Episode 74: Musketeering
|
Oct 18, 2024 |
|
Episode 73: The Politics of Delivering Trivial Changes
|
Oct 11, 2024 |
|
Episode 72: Perfectionism in Programming
|
Oct 04, 2024 |
|
Episode 71: Are Ignorable Errors Still "Errors"?
|
Sep 27, 2024 |
|
Episode 70: Resource Engineering
|
Sep 20, 2024 |
|
Episode 69: Anxiety When Fixing a System You Didn't Create
|
Sep 13, 2024 |
|
Episode 68: The Fallacy of Rewriting Software to Save Money
|
Sep 06, 2024 |
|
Episode 67: Revisiting "The Joel Test: 12 Steps to Better Code"
|
Aug 30, 2024 |
|
Episode 66: Squashing the Right Bugs
|
Aug 23, 2024 |
|
Episode 65: Exploring Different Perspectives on Risk with Dustin Rea
|
Aug 09, 2024 |
|
Episode 64: Aligning Yourself With the Company's Risk Profile
|
Aug 02, 2024 |
|
Episode 63: Fulfilling Friday: SMS Spamming Saved
|
Jul 26, 2024 |
|
Episode 62: The Peculiar Failure of Correctly Predicting Problems
|
Jul 19, 2024 |
|
Episode 61: Challenges of Multi-Product Platforms ft. Dustin Rea
|
Jul 12, 2024 |
|
Episode 60: Anybody Could Have Done It...But I Actually Did
|
Jul 05, 2024 |
|
Episode 59: The Myth of the Boy Scout Rule
|
Jun 28, 2024 |
|
Episode 58: When You Can’t Iterate
|
Jun 14, 2024 |
|
Episode 57: White Label CRM Updates with Dustin Rea
|
Jun 07, 2024 |
|
Episode 56: AI-Driven Testing
|
May 31, 2024 |
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Episode 55: Writing Your Job Out Of Existence
|
May 24, 2024 |
|
Episode 54: Shadow Your Colleagues
|
May 17, 2024 |
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Episode 53: Cloud Infrastructure "Rewrites"
|
May 10, 2024 |
|
Episode 52: The Two-Clock Problem
|
May 03, 2024 |
|
Episode 51: How Company Culture Impacts Code Delivery
|
Apr 26, 2024 |
|
Episode 50: Fulfilling Friday - Saving Customers Millions
|
Apr 19, 2024 |
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Episode 49: Falsehoods Programmers Believe About Projects Part 2
|
Apr 12, 2024 |
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Episode 48: Falsehoods Programmers Believe About Projects
|
Apr 05, 2024 |
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Episode 47 - Maintenance Work as a Flight to Safety - A Manager's Perspective
|
Mar 29, 2024 |
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Episode 46: Workshopping Live with Dustin Rea
|
Mar 22, 2024 |
|
Episode 45 - Year In Review
|
Mar 15, 2024 |
|
Episode 44 - Do More With Less
|
Mar 08, 2024 |
|
Episode 43: Rewriting in the Age of AI
|
Mar 01, 2024 |
|
Episode 42: Iteration as a Defense From Micromanagement
|
Feb 23, 2024 |
|
Episode 41: Rewrites from a Manager's Perspective with Ryan Cowan
|
Feb 16, 2024 |
|
Episode 40: Convincing Emotionally-Committed Colleagues It's Not Worth It
|
Feb 09, 2024 |
|
Episode 39 - Project Risk with Jonathan Stark
|
Feb 02, 2024 |
|
Episode 38 - Maintenance Work as a Flight to Safety
|
Jan 26, 2024 |
|
Episode 37: Interview Insights - Changing the Game for Interviewers and Candidates
|
Jan 19, 2024 |
|
Episode 36: Becoming an Expert in your Company's Business
|
Jan 12, 2024 |
|
Episode 35: The Subtle Art of Refusing Meetings
|
Jan 05, 2024 |
|
Episode 34: (F*ck-Up Friday Series) Don’t Fix What Ain’t Broken
|
Dec 29, 2023 |
|
Episode 33: How to be a Terrible Teammate
|
Dec 22, 2023 |
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Episode 32: Getting Started with Brownfield Testing (Part 2)
|
Dec 15, 2023 |
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Episode 31: Getting Started with Brownfield Testing (Part 1)
|
Dec 08, 2023 |
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Episode 30: Investing in Yourself Beyond Education
|
Dec 01, 2023 |
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Episode 29: (F*ck-Up Friday Series) The Saleswoman Who Faked Cancer
|
Nov 24, 2023 |
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Episode 28: Making Non-Compatible Changes During Long-Running Upgrades
|
Nov 16, 2023 |
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Episode 27: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 2
|
Nov 09, 2023 |
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Episode 26: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 1
|
Nov 03, 2023 |
|
Episode 25: A Rewrite Success Story with Brian Genisio from Khan Academy
|
Oct 26, 2023 |
|
Episode 24: When AI Writes Your Documentation
|
Oct 20, 2023 |
|
Episode 23: Live Workshop with Rob Gonnella
|
Sep 22, 2023 |
|
Episode 22: Running an Iterative Refactoring Workshop
|
Sep 14, 2023 |
|
Episode 21 - Impostor Syndrome
|
Sep 08, 2023 |
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Episode 20 - Shrink Mode
|
Aug 31, 2023 |
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Episode Nineteen - The Beachhead Strategy
|
Aug 25, 2023 |
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Episode Eighteen - Strategies for Upgrading Software
|
Aug 12, 2023 |
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Episode Seventeen (F*ck-Up Friday Series) - Losing $1 billion for 4 hours
|
Jul 28, 2023 |
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Episode Sixteen - Tricks to Facilitate Conversation
|
Jul 21, 2023 |
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Episode Fifteen - Red Flag Development Ideas
|
Jul 07, 2023 |
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Episode Fourteen - How do you define ‘Minimum Viable Product’?
|
Jun 29, 2023 |
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Episode Thirteen - Transitioning from Microservices to Monolith with Josh Beckman
|
Jun 14, 2023 |
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Episode Twelve - Company Culture Pt. 2 with Thomas Morris
|
Jun 07, 2023 |
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Episode Eleven - You Can’t Build to Spec
|
Jun 01, 2023 |
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Episode Ten - The Rewrite Cycle
|
May 24, 2023 |
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Episode Nine (F*ck-Up Friday Series) - How Our Customers Got Raided by the FBI
|
May 19, 2023 |
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Episode Eight - Transforming your Internal Software into a SaaS with Brian Begy
|
May 11, 2023 |
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Episode Seven - Risk
|
May 03, 2023 |
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Episode Six - How Company Culture Makes Or Breaks Your Team
|
Apr 27, 2023 |
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Episode Five - Perverse Incentives
|
Apr 19, 2023 |
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Episode Four - Nozomi
|
Apr 13, 2023 |
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Episode Three - Why You Hate Testing
|
Apr 08, 2023 |
|
Episode Two - Iteratively Replace
|
Mar 22, 2023 |
|
Episode One
|
Mar 16, 2023 |