Do you feel like you're hitting a wall with your existing software projects? Are you curious to hear how other people are navigating this? You're not alone. On the Maintainable Software Podcast, Robby speaks with seasoned practitioners who have overcome the technical and cultural problems often associated with software development. Our guests will share stories in each episode and outline tangible, real-world approaches to software challenges. In turn, you'll uncover new ways of thinking about…
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Drawing from his experience at PagerDuty, Sentry, and now FusionAuth, he joins Robby to explore what happens when software becomes trusted infrastructure. Their conversation touches on API design, naming things, product management, self-hosted software, and why customers rarely upgrade as quickly as we’d like them to. They also discuss why “boring” software is often the most successful, how…
Machine learning systems can degrade even when the underlying code has not changed. Diana Pfeil of Sunbeam Consulting joins Robby Russell on Maintainable to explain how changing data, model behavior, and non-deterministic outputs create a different kind of maintenance challenge. Rather than asking whether a system is simply correct or incorrect, teams need reliable ways to measure confidence in…
What does it take to keep a product healthy after more than 15 years of continuous evolution? In this episode, Robby Russell talks with Chris Coyier, co-founder of CodePen, about the long game of maintaining software. Chris shares how CodePen has evolved over time, the trade-offs involved in migrating parts of the platform from Rails to Go, and the challenges of balancing maintenance work with the…
Sally Lait joins Robby Russell on Maintainable to explore software maintainability through a different lens… not just code quality, but how teams work together over time. Sally is a fractional technology leader and advisor with more than two decades in the industry. You can follow her on LinkedIn or Mastodon . They start with a familiar question: what makes software well maintained? Structure and…
Software maintenance is often framed as a technical problem. Refactoring code, fixing bugs, or upgrading dependencies. In this conversation, Robby Russell talks with Rein Henrichs about a different lens, one centered on understanding. Rein is a Principal Software Engineer at Procore , where he works within a large, long-lived system used across the construction industry. Rather than focusing on…
Software doesn’t become hard to maintain only because the code is messy. It often becomes hard to maintain because the reasoning behind it disappears. In this episode of Maintainable , Robby Russell talks with Russ Olsen about trade-offs, legacy systems, and why maintainability depends on context more than dogma. Russ brings decades of experience across very different kinds of systems, each with…
Long-lived software systems rarely stay tidy. Over time they accumulate decisions, workarounds, and layers of history that can make even simple changes feel risky. For engineers responsible for maintaining those systems, the challenge often becomes less about writing new code and more about understanding what already exists. In this episode of Maintainable, Robby Russell speaks with Joel Oliveira,…
Maintaining software over time rarely fails because of one bad decision. It fails because teams stop getting clear signals… and start guessing. In this episode, Robby talks with Lucas Roesler , Managing Partner and CTO at Contiamo . Lucas joins from Berlin to unpack what maintainability looks like in practice when you are dealing with real constraints… limited context, missing documentation, and…
Rewrites are seductive. Clean slates promise clarity, speed, and “doing it right this time.” In practice, they’re often late, over budget, and quietly demoralizing. In this episode of Maintainable , Robby sits down with Brittany Ellich , a Senior Software Engineer at GitHub , to talk about a different path. One rooted in stewardship, readability, and resisting the urge to start over. Brittany’s…
Kent Beck: You’re Ignoring Optionality… and Paying for It In this episode of Maintainable , Robby speaks with Kent Beck , a foundational voice in modern software development and author of Tidy First? . Kent joins from California to explore why optionality is a central, often underestimated dimension of maintainable software. Kent begins by describing the tension between features and future…
