Never Rewrite

Never Rewrite

‘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.

Episodes

August 8, 2025 21 mins

Isaac Askew and Jeffrey Sherman discuss the ongoing debate between end-to-end tests and unit tests in software development. The discussion delves into the implications of the testing pyramid, the potential future of testing with AI, and the evolving role of product teams in the testing process. They emphasize the need for a balanced approach to testing, cautioning against over-reliance on end-to-end tests while recognizing their va...

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In this episode of Never Rewrite, hosts Isaac Askew and Jeffrey Sherman engage with Spriha Tucker, the Field CTO at BuildKite, to explore the intricacies of Continuous Integration and Continuous Deployment (CI/CD). They discuss the importance of deployment in CI/CD practices, the significance of feedback loops in iterative development, and the necessity of understanding customer context for effective solutions. Spriha shares insigh...

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Isaac and Jeffrey discuss why abandoned projects or failed rewrites have code that always seems to just linger - is it worth fixing?

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In this episode of Never Rewrite, Isaac Askew and Jeffrey Sherman emphasize the importance of understanding customer needs and the risks associated with maintaining old features while developing new ones. The conversation highlights the value of iterative delivery and the significance of API versioning in ensuring a smooth transition for users. Ultimately, they advocate for a pivoting approach rather than a complete rewrite, allowi...

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Today we highlight he significant impact and costs associated with hidden business rules in software development. We explore the challenges of implementation, the importance of documenting business rules effectively, and how AI can assist in managing these rules. Our discussion emphasizes the need for an internal product book to consolidate knowledge and improve communication among teams, ultimately leading to more efficient develo...

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Isaac Askew and Jeffrey Sherman discuss the social and emotional ramifications of failed rewrites in project management. They explore the loss of patience from leadership, the burnout experienced by teams, and the importance of taking responsibility for project outcomes. The discussion emphasizes the need for teams to salvage lessons from failures and to approach leadership with solutions rather than just problems. The conversation...

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Isaac Askew, Dustin Rea, and Jeffrey Sherman delve into the complexities of developing Minimum Viable Products (MVPs) and the challenges of balancing simplicity with the need for future scalability. They discuss the Goldilocks problem in software development, emphasizing the importance of finding the right balance between over-engineering and under-engineering. The discussion highlights the distinction between maintainability and o...

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Today we discuss the relationship between Conway's Law and software quality, exploring how a company's structure and culture can impact code quality. We delve into the signs of a toxic culture, the consequences of a 'yes culture', and strategies for identifying and changing company culture. The conversation emphasizes the importance of communication patterns and the long-term nature of cultural transformation in org...

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We debate the merits of consolidating technology stacks versus diversifying them. Today we explore the implications of each approach on business value, engineering efficiency, and organizational dynamics. Key points include the importance of evaluating the business value of consolidation, the impact on developer fungibility, and the balance between engineering optimization and business leverage.

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Jeffrey and Isaac dive into a comment made by Allen Holub to 'rebuild' instead of 'rewriting' legacy software and dive into the terminology.


Show Notes:‪

Allen Holub's thread mentioned: https://bsky.app/profile/allenholub.bsky.social/post/3lmcyvi3kag2f

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Isaac and Jeffrey explore how to halt a rewrite, the importance of learning from the process, and how to effectively communicate changes in direction to a team. The conversation emphasizes the value of reframing discussions around rewrites to focus on new insights and solutions rather than perceived failures.

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Guest Nick Gerace discusses the rewrite of the core engine at System Initiatives, detailing the challenges faced, the technical decisions made, and the importance of aligning development with business goals. The conversation covers the transition from the old engine to the new, the role of user feedback, and the iterative process that led to a more efficient and user-friendly product.


Show Notes:

Domain-Driven Design book: https:...

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Guest Paul Stack shares his experiences in transforming a massive logging infrastructure from a monolithic architecture to a microservices-based system. He discusses the challenges faced during the transition, the implementation of Kafka for log management, and the importance of data retention and cost management. The conversation highlights the evolution of logging practices and the empowerment of teams through decentralization, u...

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Isaac and Jeffrey discuss the challenges and signs of failing rewrites in software development.

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Nick Stinemates from System Initiative joins us to explore the complexities and challenges of software rewrites. We discuss the nuances between rewrites and refactors, the pitfalls of full rewrites, and the importance of incremental changes. The conversation delves into team dynamics during rewrites, the existential reasons that can drive a rewrite, and the parallels between software rewrites and software adoption.

Show Notes:

Nick&#...

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April 25, 2025 15 mins

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...

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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...

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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 governm...

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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 impa...

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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...

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