

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

17 snips
Aug 1, 2025 • 37min
Episode 115: [CI/CD] Beautiful Feedback Loops with guest Spriha Tucker
Spriha Tucker, Field CTO at BuildKite and former founder of Aviator, dives deep into CI/CD practices. She discusses the pivotal role of feedback loops in agile development to enhance code quality and align products with user needs. Spriha highlights innovative rapid prototyping strategies and the necessity of authentic customer relationships. The conversation also covers the importance of data visualization in improving developer experiences and scaling organizational success, emphasizing that it's all about delivering real value through effective collaboration.

Jul 25, 2025 • 21min
Episode 114: Old Projects Never Die, They Just Fade Away
Isaac and Jeffrey discuss why abandoned projects or failed rewrites have code that always seems to just linger - is it worth fixing?

Jul 18, 2025 • 12min
Episode 113: Do You Want a Better Version of What You Have?
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, allowing for a more adaptive and responsive development process.(Isaac used the wrong microphone for recording and Jeffrey said nothing...)

Jul 11, 2025 • 19min
Episode 112: The Impact & Cost of Hidden Business Rules
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 development processes.

Jul 4, 2025 • 14min
Episode 111: The Social Aspects of a Failed Rewrite
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 concludes with strategies for ensuring future success and maintaining trust within teams.Chapters00:00 The Impact of Failed Rewrites03:03 Team Dynamics and Leadership Pressure06:01 Salvaging Lessons from Failure09:00 Taking Responsibility for Project Outcomes12:02 Strategies for Future Success

Jun 27, 2025 • 27min
Episode 110: MVPs, YAGNI, and the Goldilocks Problem
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 optionality, the significance of timing in product development, and the lessons learned from past experiences. The trio also explores the concept of gaming out scenarios to prepare for potential challenges and the importance of aligning teams to ensure a cohesive approach to development.

Jun 20, 2025 • 20min
Episode 109: Conway's Law and Software Quality
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 organizations.

Jun 13, 2025 • 16min
Episode 108: Consolidating Tech Stacks - Is It Worth It?
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.

Jun 6, 2025 • 14min
Episode 107: Rebuilding vs. Rewriting vs. Refactoring?
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

May 30, 2025 • 15min
Episode 106: How to Stop a Rewrite in Progress
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.