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Maintainable

Robby Russell

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 how to improve your software project's maintainability.

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20 episodes
Avg 55 min
English

Episodes 20

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#225
August 18 · 55 min
David Hayes: Boring Software, Clear Incentives, and Better Checklists
David Hayes believes maintainable software starts with a simple idea: fitness for purpose.
#224
August 4 · 48 min
Diana Pfeil: Building Confidence in Probabilistic Systems
Software powered by AI can change its behavior without a deployment, leaving teams to maintain code, data, prompts, models, and the uncertainty between them. Diana Pfeil joins Robby to explain how evals, production monitoring, and a preference for simpler models help teams build confidence in systems they cannot completely predict.
#223
June 16 · 54 min
Chris Coyier: The Long Game of Maintaining CodePen
Chris Coyier, co-founder of CodePen, joins Robby to reflect on what it takes to maintain software over the long haul. Drawing from CodePen’s 15-plus-year journey, Chris shares lessons about balancing stability with innovation, navigating technical debt, and gradually evolving a product without losing sight of the people who depend on it. They discuss CodePen’s origins, the team’s ongoing migration from Rails to Go, the realities of building with a small engineering team, and why maintainabilit
#222
May 5 · 55 min
Sally Lait: Confidence Is the Real Metric
Sally Lait joins Robby to explore why confidence might be the most important signal of software maintainability. They dig into the cultural dynamics behind legacy systems, why technical debt becomes a people problem, and how teams can move forward without dismissing the work that got them here.
#221
April 14 · 55 min
Rein Henrichs: The Real Work of Maintenance Happens Before You Touch the Code
Most teams treat maintenance like a coding problem. Rein Henrichs argues the real work starts much earlier… in how teams understand the system in the first place.
#220
March 31 · 54 min
Russ Olsen: The Hidden Cost of Forgetting Why the Code Looks Like That
Russ Olsen joins Robby to talk about maintainability, trade-offs, and why so many teams forget to document what they decided not to do. It’s a conversation about legacy systems, rewrites, developer quality of life, and the stories software teams need to tell each other better.
#219
March 17 · 1 hr 1 min
Joel Oliveira: Predictability Is a Maintainability Feature
Predictability might be the most underrated feature of maintainable software. Joel Oliveira joins Robby to explore how thoughtful patterns, small refactors, and a bit of stubborn persistence can keep systems healthy long after their first release.
#218
February 3 · 54 min
Lucas Roesler: The Fast Feedback Loop Advantage
What if maintainability isn’t about rewriting code, but about designing better feedback loops? Lucas Roesler joins Robby to unpack simplicity, observability, and the hard reality of inheriting opaque systems. A conversation about seeing software clearly… before changing it.
#217
January 21 · 1 hr
Brittany Ellich: Using AI to Maintain Software, Not Rewrite It
AI isn’t here to save you from your codebase. Brittany Ellich explains how to use it to maintain what already works… without chasing rewrite fantasies or shipping chaos.
#216
Dec 9, 2025 · 49 min
Kent L Beck: You’re Ignoring Optionality… and Paying for It
Kent Beck and Robby unpack why teams burn optionality faster than they realize and why restoring it isn’t a luxury—it’s the work. They explore reversible vs irreversible decisions, the feature saw, and what happens when teams never invest between releases. Kent makes the case for tidying as both an economic and moral responsibility.
#215
Dec 2, 2025 · 50 min
Don MacKinnon: Why Simplicity Beats Cleverness in Software Design
In this conversation, Robby speaks with Don MacKinnon, Lead Architect and Engineering Manager at Searchcraft, about reducing unnecessary complexity, choosing the right abstractions, and designing software for the long haul.
#214
Nov 18, 2025 · 49 min
Chris Zetter: Building a Database to Better Understand Maintainability
Software engineer and author Chris Zetter joins Robby to explore how pairing, documentation, and boring technology help teams build software that lasts. They unpack the real meaning of technical debt, how to guide junior engineers with confidence, and what building a database from scratch can teach us about architecture.
#213
Oct 28, 2025 · 1 hr 6 min
Denis Rechkunov: When Consistency Becomes a Culture
At Elastic, Denis Rechkunov believes code consistency is more than a style guide — it’s a cultural practice. Robby and Denis explore how automation, empathy, and small rituals help teams write code that stays cohesive long after its authors move on.
#212
Oct 14, 2025 · 54 min
Nathan Ladd: Relentless Improvement and the Cost of Neglect
In this conversation, Robby and Nathan Ladd, Principal at Brightworks Digital, explore what makes software sustainable in practice. Nathan argues that perfectly maintained software may be a myth, but that doesn’t stop teams from pursuing habits that reduce the burden of maintenance. He shares why keeping dependencies fresh, aligning around living standards, and fixing defects as they appear are all crucial to staying ahead.
#211
Aug 26, 2025 · 55 min
Taylor Otwell: What 14 Years of Laravel Taught Me About Maintainability
Taylor Otwell looks back on 14 years of building and maintaining Laravel. From four stars on GitHub to a full-fledged ecosystem, he shares what it takes to design software that lasts—and why simple often wins.
#210
Jul 22, 2025 · 53 min
Sara Jackson: Why Resilience Is a Team Sport
What happens when you treat resilience as a shared responsibility across your team, not just an infrastructure concern? Sara Jackson unpacks the value of documentation, application-layer chaos experiments, and test suites you can actually trust.
#209
Jul 1, 2025 · 56 min
Joel Chippindale: Why High-Quality Software Isn’t About Developer Skill Alone
Is high-quality code really just about developer skill? According to CTO coach Joel Chippindale, the key to maintainable software often lies in the conversations you have before writing a single line of code. In this episode, we explore how to reframe technical debt, build cross-team trust, and make legacy systems easier to change.
#208
Jun 10, 2025 · 49 min
Melanie Sumner: Why Continuous Accessibility Is a Strategic Advantage
What if accessibility wasn’t a checklist—but an integrated part of your development workflow? Melanie Sumner shares how her team at HashiCorp is building with purpose and why continuous accessibility gives them a lasting edge.
#207
May 20, 2025 · 55 min
Joe Masilotti: Simplify Your Stack, Ship Mobile Sooner
Consultant Joe Masilotti shares why most mobile apps don’t need to be fully native, how he helps Rails developers simplify their stack, and what it means to be a respectful guest in someone else’s codebase.
#206
Apr 22, 2025 · 1 hr 3 min
Freedom Dumlao: What 70 Java Services Taught Me About Focus
Freedom Dumlao made the rare decision to rebuild a microservices platform as a monolith. In this episode, he shares why—and how it made his team more effective. Plus, we talk Java, Rails, AI, and how not to drown in decision-making.

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