Don MacKinnon: Why Simplicity Beats Cleverness in Software Design

More from Maintainable

1. 

   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.

2. 

   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.

3. 

   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.

4. 

   E214 · 18 Nov 2025 · 50 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.

5. 

   E213 · 28 Oct 2025 · 1 hr 7 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.

6. 

   E212 · 14 Oct 2025 · 55 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.

7. 

   E229 · 6 Oct 2026 · 54 minNew

   Matija Šošić: Abstractions Aren’t Going Anywhere

   What happens to frameworks when generating code becomes cheap enough that nobody particularly cares about the boilerplate anymore? Matija Šošić joins Robby to talk about boring software, abstraction as a form of restraint, Wasp’s decision to abandon its custom DSL, and why AI may make good abstractions more valuable rather than less.

8. 

   E228 · 29 Sep 2026 · 54 min

   José Valim: Designing a Language You Can Maintain for Decades

   What changes when the software you’re maintaining is a programming language that thousands of other applications depend on? José Valim joins Robby to trace Elixir from a frustrating Rails concurrency bug to a language designed for long-term evolution, then looks at how AI is changing documentation, dependencies, coding tools, and open-source maintenance.

9. 

   E227 · 8 Sep 2026 · 1 hr 22 min

   John Athayde: Maintaining the User Side of Software

   The user interface of a long-lived application carries years of technical decisions, design choices, and organizational history. John Athayde joins Robby to explore how teams can untangle that front-end sprawl, and what changes when AI makes it much easier to analyze and rewrite what came before.

10. 

    E226 · 1 Sep 2026 · 54 min

    Kristin Isaac: The Customer Doesn’t Care About Your Technical Debt

    Customers don’t ask you to pay down technical debt. They notice when the product is slow, unreliable, or keeps breaking in the same damn way. Kristin Isaac joins Robby to explore how engineers can translate invisible maintenance work into customer and business impact… and why that skill may become even more important as AI makes software faster to create than to understand.

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