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 flexibility. Shipping new capabilities is easy to measure. Creating options for what comes next is not. That imbalance is where maintainability either flourishes or collapses. Senior developers in particular must learn to navigate this tension because they have lived through the consequences when no one does.

They reflect on how cost models have shifted across the last five decades. Early in Kent’s career, computers were expensive and programmers were cheap. Today the balance often flips depending on scale. At massive scale, electricity and compute time become meaningful costs again. That variability shapes whether teams optimize for hardware efficiency or developer efficiency.

Episode Highlights

[00:00:46] The Two Forms of Software Value

Kent explains why software value comes from both current features and the options you preserve for future work. He describes optionality as the invisible half of maintainability.

[00:03:35] When Computers Become “Expensive” Again

Robby and Kent revisit the shift from hardware-optimized development to developer-optimized development and how large-scale systems have reintroduced compute cost pressures.

[00:07:25] Why the Question Mark in Tidy First?

Kent shares why tidying is always a judgment call and why he put a question mark in the title.

[00:10:14] The Real Cost of Speculative Flexibility

They discuss why adding configurability too early creates waste and why waiting until just before you need it increases value.

[00:13:46] Making Hard Changes Easy

Kent outlines his guiding idea. When you face a difficult change, make the change easy first, then make the easy change.

[00:17:08] The Feature Saw

Kent explains his features versus options graph and how teams repeatedly burn optionality until they hit zero. At that point, forward movement becomes painful.

[00:19:37] Why 100 Percent Utilization Is a Trap

Kent discusses how queuing theory shows that full utilization pushes wait times toward infinity. Overcommitted teams have no room for design work.

[00:22:44] Split Teams Do Not Solve the Problem

Robby talks about consulting scenarios where “tidy teams” and “feature teams” are separated. Kent argues that this splits incentives and prevents optionality from being sustained.

[00:26:15] Structure and Behavior Should Not Ship Together

Kent describes why feature changes are irreversible, structure changes are reversible, and why combining them increases risk for everyone.

[00:30:37] Tidying Reveals Intent

While cleaning up structure, developers often uncover logic flaws or misunderstandings that were previously hidden.

[00:32:00] When Teams Discourage Testing

Kent shares stories about environments where developers were punished for refactoring or writing tests. He explains why building career options is essential in those situations.

[00:37:57] Why Tidying Is an Ethical Obligation

Kent reframes optionality as a moral responsibility. No one should make work harder for the next person who touches the code.

[00:41:33] Succession and Slicing

Kent describes how nearly every structural change can be broken into small, safe steps, even when the change first appears atomic.

[00:47:00] A Small Habit to Start Today

Kent suggests adding a blank line to separate conceptual chunks in long functions. It is a small step that improves clarity immediately.

Resources Mentioned

• Tidy First? by Kent Beck
• Kent Beck on Substack
• The Timeless Way of Building by Christopher Alexander

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

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Episode Highlights

[00:00:48] What Makes Software Maintainable
Don explains why unnecessary complexity is the biggest barrier to maintainability, drawing on themes from A Philosophy of Software Design.

[00:03:14] The Cost of Clever Abstractions
A real story from a Node.js API shows how an unused abstraction layer around MongoDB made everything harder without delivering value.

[00:04:00] Shaping Teams and Developer Tools
Don describes the structure of the Searchcraft engineering team and how the product grew out of recurring pain points in client projects.

[00:06:36] Reducing Complexity Through SDK and Infra Design
Why Searchcraft intentionally limits configuration to keep setup fast and predictable.

[00:08:33] Lessons From Consulting
Robby and Don compare consulting and product work, including how each environment shapes developers differently.

[00:15:34] Inherited Software and Abandoned Dependencies
Don shares the problems that crop up when community packages fall behind, especially in ecosystems like React Native.

[00:18:00] Evaluating Third-Party Libraries
Signals Don looks for before adopting a dependency: adoption, update cadence, issue activity, and whether the library is “done.”

[00:19:40] Designing Code That Remains Understandable
Why clear project structure and idiomatic naming matter more than cleverness.

[00:20:29] RFCs as a Cultural Anchor
How Don’s team uses RFCs to align on significant changes and avoid decision churn.

[00:23:00] Documentation That Adds Context
Documentation should explain why, not echo code. Don walks through how his team approaches this.

[00:24:11] Type Systems and Maintainability
How Don’s journey from PHP and JavaScript to TypeScript and Rust changed his approach to structure and communication.

[00:27:05] Testing With Types
Stable type contracts make tests cleaner and less ambiguous.

[00:27:45] Building Trust in AI Systems
Don discusses repeatability, hallucinations, and why tools like MCP matter for grounding LLM behavior.

[00:29:28] AI in Developer Tools
Search Craft’s MCP server lets developers talk to the platform conversationally instead of hunting through docs.

[00:33:21] Improving Legacy Systems Slowly
The Strangler pattern is a practical way to replace old systems one endpoint at a time.

[00:34:11] Deep Work and Reducing Reactive Noise
Don encourages developers to carve out time for uninterrupted thinking rather than bouncing between notifications.

[00:36:09] Measuring Progress
Build times, test speeds, and coverage provide signals teams can use to track actual improvement.

[00:38:24] Changing Opinions Over a Career
Why Don eventually embraced TypeScript after initially writing it off.

[00:39:15] Industry Trends and Repeating Cycles
SPAs, server rendering, and the familiar pendulum swing in web architecture.

[00:41:26] Experimentation and Team Autonomy
How POCs and side projects surface organically within Don’s team.

[00:44:42] Growing Skills Through Intentional Goals
Setting learning targets in 1:1s to support long-term developer growth.

[00:47:19] Where to Find Don
LinkedIn, Blue Sky, and his site: donmackinnon.dev.

Resources Mentioned

• A Philosophy of Software Design by John Ousterhout
• John Ousterhout’s Maintainable.fm Interview (Episode 131)
• Searchcraft
• Elastic
• Algolia
• WordPress Plugin Directory
• Request for Comments (RFC)
• Strangler Fig Pattern
• C2 Wiki
• Model Context Protocol (MCP)
• Glam AI
• Aubrey/Maturin Series by Patrick O’Brian
• Master and Commander
• donmackinnon.dev

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

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Episode Summary

In this conversation, Robby sits down with software engineer and author Chris Zetter to explore what building a relational database from scratch can teach us about maintainability, architectural thinking, and team culture. Chris shares why documentation often matters more than perfectly shaped code, why pairing accelerates learning and quality, and why “boring technology” is sometimes the most responsible choice. Together they examine how teams get stuck in local maxima, how junior engineers build confidence, and how coding agents perform when asked to implement a database.

Episode Highlights

[00:01:00] What Makes Software Maintainable
Chris explains that well-maintained software is defined by how effectively it helps teams deliver value and respond to change. In some domains—like payroll systems—the maintainability burden shifts toward documentation rather than code organization.

[00:03:50] Documentation vs. Code Comments
He describes visual docs, system diagrams, and commit–ticket links as more durable sources of truth than inline comments, which tend to rot and discourage refactoring.

[00:05:15] Rethinking Technical Debt
Chris argues that teams overuse the metaphor. He prefers naming the specific reason something is slow or brittle—like outdated libraries or rushed decisions—because that builds trust and clarity with product partners.

[00:07:45] Where Core Debt Really Lives
Earlier in his career he obsessed over long files; now he focuses on structural issues. Architecture, boundaries, and naming affect changeability far more than messy internals.

[00:08:15] Pairing as the Default Tool
Chris loves pairing for its speed, clarity, and shared context. Remote pairing has removed obstacles like mismatched keyboard setups or cramped office seating. Tools like Tuple and Pop keep it smooth.

[00:10:20] The Mob Tool and Fast Driver Switching
He explains how the Mob CLI tool makes switching drivers nearly instant, which keeps energy high and lets everyone work in their own editor environment, reducing friction and fatigue.

[00:13:45] Pairing with Junior Engineers
Pairing helps newer developers avoid painful pull-request rework and builds confidence. But teams must balance pairing with opportunities for engineers to build autonomy.

[00:20:50] Getting Feedback Sooner
Chris emphasizes speed of feedback: showing progress early to stakeholders prevents wasted days—and sometimes weeks—of heading in the wrong direction.

[00:21:10] Boring Technology as a Feature
After being burned by abandoned frameworks, Chris champions predictable, well-supported tools for the big layers: language, framework, database. Novelty is great—but only in places where rollback is cheap.

[00:23:20] Balancing Professional Development with Organizational Needs
Developers want experience with new technology; organizations want stability. Chris describes how leaders can channel curiosity safely and productively.

[00:27:20] Build a Database Server
Chris’s book, Build a Database Server, is a practical, language-agnostic guide to building a relational database from scratch. It uses a test suite as a feedback loop so developers can experiment, refactor, and learn architectural trade-offs along the way.

[00:31:45] What Writing the Book Taught Him
Creating a database deepened his appreciation for Postgres maintainers. He highlights the number of moving parts—storage engine, type system, query planner, wire protocol—and how academic papers often skip hands-on guidance.

[00:33:00] Experimenting with Coding Agents
Chris tested coding agents by giving them the book’s test suite. They passed many tests but produced brittle, incoherent architecture. Without a feedback loop for quality, the agents aimed only to satisfy test conditions—not build maintainable systems.

[00:36:55] Escaping a Local Maxima Through a Design Sprint
Chris shares a story of a team stuck maintaining a system that no longer fit business needs. A design sprint gave them space to reimagine the system, clarify naming, validate concepts, and identify which pieces were worth reusing.

[00:40:40] Rewrite vs. Refactor
He leans toward refactor for large systems but supports small, isolated rewrites when boundaries are clear.

[00:41:40] Building Trust in Legacy Code
When inheriting an old codebase, Chris advises starting with a small bug fix or UI tweak to understand deployment pipelines, test coverage, and failure modes before tackling bigger improvements.

[00:43:20] Recommended Reading
Chris recommends _Turn the Ship Around! for its lessons on empowering teams to act with intent instead of waiting for permission.

Resources Mentioned

• Build a Database Server
• Chris Zetter’s blog
• The Mob Programming CLI Tool
• Tuple
• Pop
• Turn the Ship Around!

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

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Maintaining consistency across a sprawling codebase is one of the hardest challenges in software engineering. Denis Rechkunov, a Principal Software Engineer at Elastic, joins Robby to share how his team turned consistency into a cultural practice rather than a technical checklist. From managing open source projects with hundreds of contributors to experimenting safely with new patterns, Denis believes maintainability begins with shared ownership, not just clean code.

He explains how Elastic introduced automation and linters to improve cohesion without discouraging creativity. Instead of enforcing perfection across the entire system, Denis’ team scopes their changes to manageable areas and rewards steady progress over sweeping rewrites. Their annual “On Week” tradition gives engineers space to fix what frustrates them most, showing how small, focused bursts of work can produce big leaps in stability and morale.

The conversation also explores the human side of maintainability. Denis recalls early lessons about unclear expectations, the importance of documenting decisions in public pull requests, and how open feedback loops build trust across remote teams. Whether it’s stabilizing a flaky CI pipeline or mentoring new engineers, Denis argues that technical excellence thrives when consistency becomes a habit shared by everyone.

Episode Highlights

[00:01:02] Defining Well-Maintained Software
Denis identifies consistency, documentation, testability, and agility as the key ingredients of maintainable systems.

[00:02:22] Balancing Standards and Autonomy
How automation and linters help preserve code cohesion while minimizing interpersonal friction.

[00:04:08] Experimenting Safely
Elastic scopes new patterns to low-risk modules before broader adoption, avoiding mass rewrites.

[00:07:19] Incremental Cleanup
Linters only apply to changed files, helping the team fix issues gradually without overwhelming contributors.

[00:08:02] Maintainability as a People Problem
Denis highlights that sustainable systems depend more on culture and mentorship than on architecture.

[00:10:13] Lessons from Miscommunication
An early experience showed the cost of undocumented conventions and unclear onboarding.

[00:17:09] Making Space for Technical Debt
Elastic’s engineers dedicate part of each sprint and an annual “On Week” to tackle maintenance work.

[00:23:05] Restoring CI Reliability
Denis shares how the team revived a pipeline with only a 10% success rate by categorizing failures and focusing on data.

[00:32:00] Practicing Software Archaeology
He stresses the value of documenting discussions in pull requests to avoid historical guesswork later.

[00:36:09] Feedback and Trust
Open communication, humility, and mutual feedback loops form the backbone of a maintainable culture.

[00:51:00] Embracing Chaos in Open Source
Denis encourages teams to accept a degree of entropy and focus their efforts on user-facing stability.

[01:00:00] Security and Privacy
Why maintainability, trust, and privacy are inseparable pillars of long-term sustainability.

[01:01:06] Where to Start
Instead of rewriting code, start by cultivating maintainability as a shared value across the team.

Resources Mentioned

• Elastic
• golangci-lint
• AppSignal
• The Caves of Steel by Isaac Asimov — Denis’ recommendation inspired Robby to finally pick up a copy and start reading it himself.
• Denis’s Blog – rdner.de
• Denis on GitHub
• Denis on Mastodon
• Denis on LinkedIn

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

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Or search "Maintainable" wherever you stream your podcasts.

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Episode Notes

The discussion moves into how standards evolve beyond tools, the trade-offs of monocultures vs. consensus-driven teams, and why ownership matters when the original authors move on. Nathan also unpacks the cost of neglect, describing defects as anything that slows developers down—not just issues that impact end users.

Later in the conversation, Nathan recounts a migration from a React SPA to Turbo and Stimulus that removed barriers between designers and developers. He highlights how keeping all problems on the radar together prevents teams from falling into local optima. The episode closes with reflections on TestBench, blind spots in testing, continuous improvement in remote teams, and advice for developers who feel stuck raising maintenance concerns.

Episode Highlights

[00:01:07] Defining Well-Maintained Software: Nathan shares his three key markers—up-to-date dependencies, adherence to team standards, and fixing defects immediately.

[00:02:53] From Tools to Tacit Knowledge: Why norms start with tool-enforced rules like RuboCop but evolve into cultural agreements within teams.

[00:04:49] Speed vs. Durability: Teams built on monoculture move quickly early on, but diverse, consensus-driven cultures go farther.

[00:11:11] Owning the Architecture: When original developers leave, new teams must take responsibility for architecture rather than defer decisions.

[00:13:37] The Cost of Neglect: Dependencies, drifting standards, and defects interact in compounding ways. Nathan reframes defects as “anything that impedes developer effectiveness.”

[00:17:46] React → Turbo + Stimulus Migration: A costly SPA and siloed design team gave way to a simpler approach that reduced rework and empowered designers to contribute directly.

[00:22:44] Avoiding Local Optima: Tackling problems in isolation creates dead ends—addressing them holistically opens real paths forward.

[00:24:32] Who We Seek Validation From: Developer identities often align with whose approval they value—shaping front-end vs. back-end divides.

[00:27:34] Comfort vs. Maintenance Burden: Silos built for comfort create tomorrow’s maintenance problems.

[00:33:45] Relentless Improvement in Remote Teams: Start as an ensemble, evolve into autonomous work cells, and use work logs to sustain consensus.

[00:38:33] What’s Missing from Remote Work: Nathan reflects on lost “hallway conversations” and the challenge of building social glue remotely.

[00:40:50] The Story Behind TestBench: Dissatisfaction with existing frameworks and a desire for simplicity led to TestBench’s creation.

[00:47:38] Testing Blind Spots: The biggest blind spot is equating testing with automation—interactive testing and intelligible output remain essential.

[00:50:35] Advice for Stuck Engineers: Nathan encourages developers to study quality traditions, connect with peers, and embrace continuous improvement.

[00:53:16] Book Recommendations: Deming’s Out of the Crisis and The New Economics, Toyota’s product development work, and Rawls’ A Theory of Justice.

Tools & Resources Mentioned

• Brightworks Digital – Nathan’s current company, where he serves as Principal.
• Nathan Ladd on LinkedIn – Connect with Nathan and follow his work.
• TestBench – A Ruby testing framework co-created by Nathan.
• Turbo – Hotwire framework for building modern, fast applications without heavy JavaScript.
• Stimulus – A modest JavaScript framework for enhancing HTML with small, reusable controllers.
• RSpec – A popular Ruby testing tool for behavior-driven development.
• Minitest – A simple and fast Ruby testing framework.
• RuboCop – A Ruby static code analyzer and formatter.
• Lessons Learned in Software Testing – Classic book on testing by Cem Kaner, James Bach, and Bret Pettichord.
• Out of the Crisis – W. Edwards Deming’s influential work on quality and systems thinking.
• The New Economics – Deming’s follow-up book on continuous improvement.
• A Theory of Justice – John Rawls’ seminal work on moral and political philosophy.
• The Toyota Product Development System – Insights into Toyota’s continuous improvement and development practices.

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

• Apple Podcasts
• Spotify

Or search "Maintainable" wherever you stream your podcasts.

Keep up to date with the Maintainable Podcast by joining the newsletter.

Taylor Otwell, creator of Laravel and CEO of Laravel LLC, joins Robby to reflect on his 14-year journey building and maintaining one of the most popular web frameworks in the world. From its PHP 5.3 origins to a full-time business with a 70-person team, Taylor shares what he's learned about code maintainability, developer experience, and what it means to evolve without overcomplicating things.

He discusses the importance of simplicity in software design, why sticking to framework conventions leads to better long-term outcomes, and how his minimalist mindset continues to shape Laravel today. Taylor also opens up about the moment he felt out of ideas, how Laravel’s 2024 funding round marked a new chapter, and what it’s like to hand off more responsibility while staying involved in the open source core.

Episode Highlights

[00:01:07] Taylor’s Definition of Maintainable Software  
Simplicity, understandability, and confidence in making changes are key themes in Taylor's approach to longevity in software.

[00:02:13] Kenny vs. the Terminator: A Metaphor for Code  
Why Taylor believes software should be disposable and adaptable, not rigid and overbuilt.

[00:05:39] Laravel’s Unexpected Traction  
Taylor shares the early days of Laravel and the moment he realized the project had legs.

[00:10:30] Who Laravel Is Built For  
Taylor talks about designing for the “average developer” and balancing his own preferences with those of a broader community.

[00:14:50] Curating a Growing Project—Solo  
Despite Laravel’s scale, Taylor remains the sole curator of the open source core and explains why that hasn’t changed (yet).

[00:18:00] From Scripts to Business  
How Laravel’s first commercial product came out of a personal need—and pushed Taylor to go full time.

[00:20:00] Making Breaking Changes  
Taylor explains Laravel’s evolution and why he now tries to avoid breaking backward compatibility.

[00:25:00] Stick to the Conventions  
The Laravel apps that age best are the ones that don’t get too clever, Taylor says—because the clever dev always moves on.

[00:27:00] Recognizing “Cleverness” as a Smell  
Advice for developers who may unknowingly be over-engineering their way into future technical debt.

[00:30:00] Making Decisions by Comparing Real Code  
Taylor explains why he always brings discussions back to reality by looking at code side-by-side.

[00:34:00] Dependency Injection vs. Facades  
Why most Laravel developers stick with facades, and how architectural trends have changed.

[00:41:00] Laravel’s Evolution Around Static Analysis  
Taylor talks about embracing PHP's maturing type system while staying true to the dynamic roots of the framework.

[00:43:00] A Shift in Laravel’s Testing Culture  
How Adam Wathan’s course reshaped the community’s approach to feature testing in Laravel apps.

[00:48:09] What Keeps Laravel Interesting Now  
Taylor reflects on transitioning from solving his own problems to empowering a larger team—and why that’s the new challenge.

Resources & Links

• Laravel
• Laravel Changelog
• Taylor on X (Twitter)
• Taylor on Bluesky
• Elements of Style – William Strunk Jr.
• Adam Wathan's “Test-Driven Laravel” course

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

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Or search "Maintainable" wherever you stream your podcasts.

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Robby is joined by Sara Jackson, Senior Developer at thoughtbot, to explore the practical ways teams can foster resilience—not just in their infrastructure, but in their everyday habits. They talk about why documentation is more than a chore, how to build trust in test suites, and how Chaos Engineering at the application layer can help make the case for long-term investment in maintainability.

Sara shares why she advocates for writing documentation on day one, how “WET” test practices have helped her avoid brittle test suites, and why she sees ports as a powerful alternative to full rewrites. They also dive into why so many teams overlook failure scenarios that matter deeply to end users—and how being proactive about those situations can shape better products and stronger teams.

Episode Highlights

[00:01:28] What Well-Maintained Software Looks Like: Sara champions documentation that’s trusted, updated, and valued by the team.

[00:07:23] Invisible Work and Team Culture: Robby and Sara discuss how small documentation improvements often go unrecognized—and why leadership buy-in matters.

[00:10:34] Why Documentation Should Start on Day One: Sara offers a “hot take” about writing things down early to reduce cognitive load.

[00:16:00] What Chaos Engineering Really Is: Sara explains the scientific roots of the practice and its DevOps origins.

[00:20:00] Application-Layer Chaos Engineering: How fault injection can reveal blind spots in the user experience.

[00:24:36] Observability First: Why you need the right visibility before meaningful chaos experiments can begin.

[00:28:32] Pitching Resilience to Stakeholders: Robby and Sara explore how chaos experiments can justify broader investments in system quality.

[00:33:24] WET Tests vs. DRY Tests: Sara explains why test clarity and context matter more than clever abstractions.

[00:40:43] Working on Client Refactors: How Sara approaches improving test coverage before diving into major changes.

[00:42:11] Rewrite vs. Refactor vs. Port: Sara introduces “porting” as a more intentional middle path for teams looking to evolve their systems.

[00:50:45] Delete More Code: Why letting go of unused features can create forward momentum.

[00:51:13] Recommended Reading: Being Wrong by Kathryn Schulz.

Resources & Links

• Sara on Mastodon
• thoughtbot
• RubyConf 2024 Talk – Chaos Engineering on the Death Star
• Book: Being Wrong by Kathryn Schulz
• Flu Shot on GitHub
• ChaosRB on GitHub
• Semian from Shopify — a chaos engineering toolkit for Ruby

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

• Apple Podcasts
• Spotify

Or search "Maintainable" wherever you stream your podcasts.

Keep up to date with the Maintainable Podcast by joining the newsletter.

CTO coach Joel Chippindale joins Robby to share what he's learned over two decades of building and leading software teams. Joel argues that maintainability has less to do with “clean code” and more to do with how teams communicate, prioritize, and make progress visible. Drawing on his time at Unmade and his current coaching practice, Joel outlines practical ways teams can build trust, navigate brittle systems, and stop letting technical debt conversations get lost in translation.

Episode Highlights

[00:01:10] A Working Definition of Maintainability
Joel explains why “software that’s easy to keep changing” is the gold standard—and why context matters as much as code.

[00:05:24] The Pitfalls of Pre-Optimization
How developers can trap themselves by designing for futures that may never arrive.

[00:10:40] Challenging the Iron Triangle
Joel pushes back on the idea that teams must sacrifice quality for speed or cost.

[00:15:31] Quality Is a Team Conversation
Why code quality starts long before you open your editor.

[00:20:00] Unmade Case Study: From Chaos to Confidence
How Joel helped a struggling team at Unmade regain trust by delivering less—and showing more.

[00:28:08] Helping Business Stakeholders Buy Into Maintenance Work
How to reframe backend investments in terms that resonate across departments.

[00:33:40] First Steps for Fragile Systems
What Joel looks for when coaching teams overwhelmed by legacy code.

[00:41:32] The Value of Boring Technology
Why solving real problems matters more than chasing resume polish.

[00:45:20] The Case for Coaching
What makes leadership coaching valuable—and why it's not a sign of weakness.

[00:51:10] Building Your Manager Voltron
Joel shares why every developer should cultivate their own support system, including mentors, peers, and coaches.

Resources & Mentions

• Joel’s Coaching Site – Monkey’s Thumb
• Joel on Mastodon
• “Take Back Control of Code Quality” – Joel’s Blog Post
• “Manager Voltron” by Lara Hogan
• Never Split the Difference by Chris Voss

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

• Apple Podcasts
• Spotify

Or search "Maintainable" wherever you stream your podcasts.

Keep up to date with the Maintainable Podcast by joining the newsletter.

Melanie Sumner: Why Continuous Accessibility Is a Strategic Advantage

Melanie Sumner, Product Accessibility Lead for Design Systems at HashiCorp, joins Robby to talk about what it takes to scale accessibility across legacy products—and how aligning design and engineering processes creates lasting change. Melanie shares her work making Ember.js more accessible, her team’s philosophy behind their design system, and why she treats accessibility like any other technical concern.

From the pitfalls of nested interactive elements to the strengths of Ember's conventions and codemods, this conversation offers a roadmap for integrating accessibility into every layer of product development.

Melanie also reflects on why she trademarked the term Continuous Accessibility, how it fits into product lifecycles, and what other frameworks can learn from the Ember community’s approach.

“Accessibility is a technical problem with a technical solution.”

Melanie joins us from Chicago, Illinois.

Episode Highlights

[00:01:00] What Well-Maintained Software Looks Like: Consistency, purpose, and bridging design and engineering
[00:02:30] Building a Unified Design System Across 10+ Legacy Products
[00:03:30] Creating Component Requirements Before Design or Code
[00:05:00] Designing with Accessibility Defaults—and Providing Bridges for Legacy
[00:07:00] How Ember’s Conventions Help Scale Front-End Systems
[00:09:30] Who Uses Ember—and Why It's a Fit for Teams with Big Requirements
[00:13:30] Technical Debt in Design Systems and the Cost of Rushing
[00:16:30] How They Future-Proof Components and Avoid Over-Engineering
[00:19:00] What “Continuous Accessibility” Means in Practice
[00:21:00] Accessibility Testing and the Limits of Automation
[00:23:00] Common Accessibility Mistakes: Nested Interactives and Misused DIVs
[00:24:30] Keyboard Navigation as a Litmus Test
[00:26:00] Text Adventure Games and Accessibility as a Playable Experience
[00:28:30] The Origin of Her Accessibility Journey at UNC Chapel Hill
[00:31:00] Why She Avoids Framing Accessibility in Emotional Terms
[00:32:45] Compliance as a Business Driver for Accessibility
[00:35:00] Open Source Work on Testing Rules Across Frameworks
[00:38:00] The Navigation API and Fixing Single-Page App Accessibility
[00:40:30] HTML’s Forgiveness and the Illusion of “Good Enough”
[00:43:00] Advice for Engineers Advocating for Accessibility Without Authority
[00:46:45] Book Recommendation: Cradle Series by Will Wight
[00:48:30] Where to Follow Melanie: melanie.codes

Links and Resources

• Melanie's Website
• Helios Design System at HashiCorp
• Cradle Series by Will Wight
• Ember Community Survey
• A11y Automation GitHub Project
• Axe-core

Follow Melanie:

• GitHub
• LinkedIn

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In this episode of Maintainable, Robby speaks with Joe Masilotti, an independent consultant who helps Rails teams ship mobile apps using Hotwire Native.

Joe shares his perspective on what makes software maintainable—especially for consultants who need to onboard quickly. He explains why setup scripts often add unnecessary complexity, and how he evaluates a project’s maintainability by how quickly he can go from clone to coding.

Robby and Joe also discuss how hybrid mobile development can offer faster delivery, fewer bugs, and better long-term flexibility—especially when teams reuse their existing Rails web views. Joe explains how Hotwire Native allows teams to incrementally introduce native features without rewriting their entire app.

Whether you’re maintaining a mobile shell built two years ago or just starting to explore native development, Joe offers actionable advice on setting expectations, scoping client work, and navigating modern mobile tech stacks.

⏱️ Episode Highlights

[00:01:17] Onboarding as a Measure of Maintainability
Joe shares how quickly he can spin up a Rails app often reflects how maintainable it is.

[00:05:12] Being a Good Guest in Someone Else’s Codebase
Joe outlines his ideal onboarding checklist and how he adapts to unfamiliar environments.

[00:08:00] Setting Communication and Collaboration Expectations
The three questions Joe asks every client to understand how their team works.

[00:13:02] Offering Opinions—Only Where Invited
Why Joe stays scoped to the work he’s hired for, even when tempted to fix more.

[00:14:15] When Technical Debt Enters the Conversation
Joe explains how debt discussions usually emerge after version one is shipped.

[00:15:33] Who Should Read Hotwire Native for Rails Developers
Joe describes the type of developer his book is written for and what it covers.

[00:18:01] Choosing Native vs. Hybrid for Your Rails App
A framework comparison based on your current frontend architecture.

[00:20:00] Introducing the Hotwire Native Mindset
Why logic belongs on the server and the client should stay thin.

[00:21:00] Bridge Components: How Rails, iOS, and Android Connect
Joe walks through how native and web technologies pass data between layers.

[00:24:00] Why Even a Web View-Based App is Worth Shipping
The practical benefits of discoverability, push notifications, and native APIs.

[00:28:01] Replacing Unmaintainable Apps with Hotwire Native
Joe describes how hybrid rewrites often reduce mobile code by 90%.

[00:31:33] Letting Go of Feature Parity
Why most clients end up cutting features they originally wanted to preserve.

[00:32:18] Scoping and Estimating Project-Based Work
How Joe uses repeatable patterns to price fixed-fee consulting engagements.

[00:35:15] Using AI to Translate Between Tech Stacks
Joe shares how he leverages LLMs to explore unfamiliar languages like Kotlin.

[00:42:26] Long-Term Maintainability and When to Touch the Code
Why some apps don’t need changes for years—and that’s okay.

[00:43:43] Why Hybrid Apps Are Easier to Replace
Joe explains why hybrid apps are often more disposable and less risky than monolithic web apps.

🔗 Resources Mentioned:

• Joe’s Book: Hotwire Native for Rails Developers
• Joe’s Newsletter
• Hotwire Native Mindset Article
• Please Unsubscribe, Thanks by Julio Vincent Gambuto

Follow Joe on X (formerly Twitter) and visit masilotti.com to learn more.

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Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

• Apple Podcasts
• Spotify

Or search "Maintainable" wherever you stream your podcasts.

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Freedom Dumlao (CTO at Vestmark) joins Robby to explore what it means to maintain software at scale—and why teams sometimes need to unlearn the hype.

With two decades of experience supporting financial systems, Freedom shares how his team manages a Java monolith that oversees $1.6 trillion in assets. But what’s most surprising? His story of how a team working on 70+ microservices rebuilt their platform as a single Ruby on Rails monolith—and started shipping faster than ever before.

Episode Highlights

[00:02:00] Why Respecting Legacy Code Matters
Freedom reflects on a lesson he learned at Amazon: "Respect what came before." He discusses the value of honoring the decisions of past developers—especially when their context is unknown.

[00:05:00] How Tests Help (and Where They Don’t)
Freedom discusses how tests can clarify system behavior but not always intent—especially when market logic or business-specific rules come into play.

[00:07:00] The Value of Understudies in Engineering
Freedom shares how his team intentionally pairs subject matter experts with understudies to reduce risk and transfer knowledge.

[00:09:30] Rethinking Technical Debt
He challenges the fear-based framing of technical debt, comparing it instead to a strategic mortgage.

[00:17:00] From 70 Services to 1 Monolith
At FlexCar, Freedom led an unconventional rewrite—consolidating 70 Java microservices into a single Rails app. The result? A dramatic increase in velocity and ownership.

[00:25:00] Choosing Rails Over Phoenix, Laravel, and Django
After evaluating multiple frameworks, Rails' cohesiveness, Hotwire, and quick developer ramp-up made it the clear winner—even converting skeptical team members.

[00:31:00] How Rails Changed Team Dynamics
By reducing dependency handoffs, the new Rails app enabled solo engineers to own complete features. The impact? Faster delivery and more engaged developers.

[00:36:30] Why Rails Still Makes Sense at a 20-Year-Old Company
Even with a large Java codebase, Vestmark uses Rails for rapid prototyping and new product development.

[00:41:00] Using AI to Navigate Legacy Systems
Freedom explains how his team uses retrieval-augmented generation (RAG) to surface relevant code—but also the limitations of AI on older or less common codebases.

[00:51:00] Seek Feedback, Not Consensus
Freedom explains why aiming for alignment slows teams down—and how decision-makers can be inclusive without waiting for full agreement.

Links and Resources

• Freedom Dumlao on LinkedIn
• Vestmark
• No Rules Rules
• Dungeon Crawler Carl series

Thanks to Our Sponsor!

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

• Apple Podcasts
• Spotify

Or search "Maintainable" wherever you stream your podcasts.

Keep up to date with the Maintainable Podcast by joining the newsletter.