

Never Rewrite
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.
It’s not unfixable, and we explore how to get started along with an array of other software topics in our eponymous podcast.
Episodes
Mentioned books

Apr 25, 2025 • 16min
Episode 101: Relief vs. Cure
Jeffrey and Isaac explore the complex trade-off between providing immediate relief for software issues versus investing time and resources into finding a permanent cure. They discuss the implications of these choices on customer satisfaction, business budgets, and the overall health of software systems. Through real-world examples, they illustrate how sometimes quick fixes can be more practical than ideal solutions, emphasizing the importance of understanding the context and priorities of a business.

Apr 18, 2025 • 30min
Episode 100: Detecting B.S. as a Non-Technical Founder
Isaac, Dustin, and Jeffrey discuss the challenges faced by non-technical founders when working with developers. They explore issues of trust, communication, and the importance of iterative development. The discussion emphasizes the need for clear frameworks in product development, the significance of addressing technical debt and security concerns, and how to identify red flags in developer behavior. The conversation concludes with advice on balancing survival and enhancement in development and the importance of having technical expertise in-house.

Apr 11, 2025 • 37min
Episode 99: DOGE Pt. 2: Government Rewrites with Guest Dan Hon
Guest Dan Hon discusses the complexities and risks associated with rewriting government software, particularly in the context of social security systems. He emphasizes the importance of understanding legacy systems, the role of ideology in software development, and the need for transparency and user-centered design. The discussion also touches on lessons learned from the private sector and the challenges of modernization in government services.Show Notes:Dan's LinkedIn: https://www.linkedin.com/in/danhon/Dan's Newsletter: newsletter.danhon.com/ Reference to Jamie Zawinski: https://www.jwz.org/gruntle/nomo.htmlOriginal Wired.com article: https://www.wired.com/story/doge-rebuild-social-security-administration-cobol-benefits/

Apr 4, 2025 • 33min
Episode 98: DOGE's Social Security Rewrite - Killing Americans to Save Money
Isaac Askew and Jeffrey Sherman discuss DOGE's proposed rewrite of the Social Security system, focusing on the implications of transitioning from COBOL to a modern programming language like Java. They explore the motivations behind the rewrite, the challenges of legacy code, the potential role of AI, and the human cost of possible failures. The conversation culminates in predictions about the outcome of the rewrite and the impact on millions of Americans relying on Social Security.Show Notes:Wired Magazine article referenced: https://www.wired.com/story/doge-rebuild-social-security-administration-cobol-benefits/

Mar 28, 2025 • 18min
Episode 97: Fulfilling Friday - A Tattoo Scam?
Isaac tells a 'fulfilling Friday' story about how he gained the attention of a famous tattoo artist. He just needed to act quickly and send money to secure the appointment...

Mar 21, 2025 • 17min
Episode 96: Inverting the Testing Pyramid - Testing Infrastructure Changes ft. Rob Gonnella
Isaac Askew and Jeffrey Sherman discuss the complexities of testing infrastructure changes with guest Rob Gonnella. They explore the importance of building a robust testing infrastructure, the role of different types of tests, and the challenges faced when transitioning to new systems. Rob shares his experiences in developing local testing environments, engaging developers, and identifying bugs through end-to-end tests. The conversation emphasizes the need for a balanced approach to testing, particularly when making significant infrastructure changes.

Mar 14, 2025 • 5min
Episode 95: We're Writing a Book!
Never Rewrite is going analog! Out of 2000 minutes over the last two years we think we've got plenty of content to coalesce it into a book. If you have a rewrite story to share, now's your chance to get forever immortalized in the podcast hosted by two randos.

Mar 7, 2025 • 27min
Episode 94: What Did You Think You Were Saying Yes To?
Jeffrey and Isaac explore the motivations and expectations surrounding software rewrites from various stakeholders, including developers, IT leadership, product groups, marketing, finance, support, and customers. They discuss the perceived benefits and the reality of rewrites, emphasizing that while many believe rewrites will lead to improved reliability and a better work environment, the truth is that rewrites often fail to deliver on these promises.

Feb 28, 2025 • 20min
Episode 93: How to Put Work Down When Priorities Change
Isaac and Jeffrey discuss the complexities of managing work priorities in a constantly changing environment. They explore the challenges of putting work down when priorities shift, emphasizing the importance of iterative development and smaller work increments to minimize risk and maintain productivity. The discussion also touches on the balance between delivering features and building trust with users, particularly in the context of product releases that may impact customer satisfaction.

Feb 21, 2025 • 17min
Episode 92: A Framework for Prioritizing Tech Debt ft. Dustin Rea
We're joined today by Dustin Rea to discuss frameworks for prioritizing technical debt in software development. We explore the 'Jobs to Be Done' framework, emphasizing the importance of aligning engineering and product teams on customer needs. The conversation covers strategies for managing tech debt effectively, the significance of team dynamics, and the role of technical leadership in guiding prioritization efforts.


