

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

Dec 5, 2025 • 15min
Episode 133: The Consequences of Having Multiple Sources of Truth
Isaac Askew and Jeffrey Sherman discuss a humorous yet insightful story about the challenges of managing market data in financial systems, particularly focusing on the consequences of having multiple sources of truth. They explore the technical aspects of market data protocols, the issues arising from unsequenced messages, and the eventual solutions implemented to address these problems. The conversation highlights the importance of data integrity and the lessons learned from software bugs in trading systems.

Nov 28, 2025 • 7min
Episode 132: A Thankful Thanksgiving Episode
Happy Thanksgiving everybody!

Nov 21, 2025 • 51min
Episode 131: Rewrites from a Product Perspective ft. Mark Mandau
Isaac Askew and Jeffrey Sherman engage with Mark Mandau, a principal consultant, to explore the complexities surrounding software rewrites. They discuss the dual perspectives of engineering and business, highlighting case studies like Facebook and Sonos to illustrate the risks and challenges associated with rewrites. The conversation delves into the pitfalls of code freezes, the doom loop effect, and the importance of customer feedback. Mark introduces the 'peak fix' approach as a structured alternative to rewrites, emphasizing the need for early engagement with consultants to navigate these challenges effectively.

Nov 14, 2025 • 23min
Episode 130: The Pains Caused by Differing Abstractions Pt. 2 - Real World Examples
SummaryIn this episode of Never Rewrite, hosts Isaac Askew, Dustin Rea, and Jeffrey Sherman discuss the real-life implications of leaky abstractions in software development. They share personal anecdotes about the challenges faced when dealing with time zone discrepancies, database case sensitivity, and the importance of user experience. The conversation highlights the need for continuous investment in software and the lessons learned from past mistakes, emphasizing the balance between perfectionism and business viability.

Nov 7, 2025 • 18min
Episode 129: Credit Where Credit Is Due
Isaac Askew, Jeffrey Sherman, and Dustin Rea discuss the critical role of credit in management and teamwork, sharing personal experiences of idea ownership and the challenges faced in consulting environments. They emphasize the importance of recognizing contributions to foster a collaborative culture and the impact of social dynamics on idea sharing. The discussion also highlights the necessity of documenting ideas to ensure proper attribution and the broader implications of credit on team morale and organizational efficiency.

Oct 31, 2025 • 16min
Episode 128: Revisiting An Old Story With Our Current Experience
Isaac Askew and Jeffrey Sherman reflect on a past experience with a software company that made a strategic decision to extend the Objective-C compiler, ultimately leading to its downfall. They discuss the implications of this decision, the challenges faced in software development, and the lessons learned from the experience. The conversation explores the importance of making informed technology decisions, the consequences of poor project management, and the potential alternatives to rewriting software.

Oct 24, 2025 • 29min
Episode 127: The Pains Caused by Differing Abstractions
Isaac Askew, Dustin Rea, and Jeffrey Sherman discuss the complexities and challenges associated with abstractions in software development, particularly focusing on time zones and currency. They explore the engineering and product perspectives on these issues, emphasizing the importance of standardization to avoid costly bugs and inefficiencies. The discussion also touches on the social dynamics within teams, the exponential nature of complexity, and the need for clear documentation and communication across the organization to address these challenges effectively.

Oct 17, 2025 • 17min
Episode 126: Does Iterative Replacement Trap You In Legacy Frameworks?
Isaac Askew and Jeffrey Sherman explore the complexities of iterative development versus complete rewrites in software engineering. They discuss the challenges of legacy frameworks, the importance of intentionality in adopting new technologies, and the necessity of communication among teams. The discussion also highlights the Strangler Fig pattern as a viable strategy for transitioning to new frameworks while maintaining existing systems. Ultimately, they conclude that iterative development does not prevent the adoption of new frameworks and can lead to better outcomes than a Big Bang rewrite.

Oct 10, 2025 • 20min
Episode 125: Navigating Risky Software Setups
Isaac Askew and Jeffrey Sherman discuss the complexities of working with clients who have risky software setups. They explore the importance of documentation, the risks associated with development environments, and the necessity of clear communication between consultants and clients. The discussion also highlights the need for compliance and risk management strategies, particularly in financial contexts, and emphasizes the importance of establishing a staging environment to mitigate risks.

Oct 3, 2025 • 29min
Episode 124: Treating Communication Gaps Like Tech Debt ft. Austen Tucker
We're joined by guest Austen Tucker to explore the concept of communication gaps in tech environments. The discussion emphasizes the importance of setting clear expectations and using pedagogical techniques to enhance collaboration.Show notes:https://www.thearcades.me/https://www.linkedin.com/newsletters/7312541452108972032/


