Russ Olsen: The Hidden Cost of Forgetting Why the Code Looks Like That

More from Maintainable All episodes →

1. 

   E225 · 18 Aug 2026 · 55 min

   David Hayes: Boring Software, Clear Incentives, and Better Checklists

   David Hayes believes maintainable software starts with a simple idea: fitness for purpose.

2. 

   E224 · 4 Aug 2026 · 49 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.

3. 

   E223 · 16 Jun 2026 · 55 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 maintainability is often more about people than code.

4. 

   E222 · 5 May 2026 · 56 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.

5. 

   E221 · 14 Apr 2026 · 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.

6. 

   E219 · 17 Mar 2026 · 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.

7. 

   E218 · 3 Feb 2026 · 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.

8. 

   E217 · 21 Jan 2026 · 1 hr 1 min

   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.

9. 

   E216 · 9 Dec 2025 · 50 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.

10. 

    E215 · 2 Dec 2025 · 51 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.