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Maintainable

Robby Russell
Maintainable
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  • Taylor Otwell: What 14 Years of Laravel Taught Me About Maintainability
    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 & LinksLaravelLaravel ChangelogTaylor on X (Twitter)Taylor on BlueskyElements of Style – William Strunk Jr.Adam Wathan's “Test-Driven Laravel” courseThanks 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 PodcastsSpotifyOr search "Maintainable" wherever you stream your podcasts.Keep up to date with the Maintainable Podcast by joining the newsletter.
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  • Sara Jackson: Why Resilience Is a Team Sport
    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 & LinksSara on MastodonthoughtbotRubyConf 2024 Talk – Chaos Engineering on the Death StarBook: Being Wrong by Kathryn SchulzFlu Shot on GitHubChaosRB on GitHubSemian from Shopify — a chaos engineering toolkit for RubyThanks 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 PodcastsSpotifyOr search "Maintainable" wherever you stream your podcasts.Keep up to date with the Maintainable Podcast by joining the newsletter.
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  • Joel Chippindale: Why High-Quality Software Isn’t About Developer Skill Alone
    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 MaintainabilityJoel 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-OptimizationHow developers can trap themselves by designing for futures that may never arrive.[00:10:40] Challenging the Iron TriangleJoel pushes back on the idea that teams must sacrifice quality for speed or cost.[00:15:31] Quality Is a Team ConversationWhy code quality starts long before you open your editor.[00:20:00] Unmade Case Study: From Chaos to ConfidenceHow Joel helped a struggling team at Unmade regain trust by delivering less—and showing more.[00:28:08] Helping Business Stakeholders Buy Into Maintenance WorkHow to reframe backend investments in terms that resonate across departments.[00:33:40] First Steps for Fragile SystemsWhat Joel looks for when coaching teams overwhelmed by legacy code.[00:41:32] The Value of Boring TechnologyWhy solving real problems matters more than chasing resume polish.[00:45:20] The Case for CoachingWhat makes leadership coaching valuable—and why it's not a sign of weakness.[00:51:10] Building Your Manager VoltronJoel shares why every developer should cultivate their own support system, including mentors, peers, and coaches.Resources & MentionsJoel’s Coaching Site – Monkey’s ThumbJoel on Mastodon“Take Back Control of Code Quality” – Joel’s Blog Post“Manager Voltron” by Lara HoganNever Split the Difference by Chris VossThanks 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 PodcastsSpotifyOr search "Maintainable" wherever you stream your podcasts.Keep up to date with the Maintainable Podcast by joining the newsletter.
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  • Melanie Sumner: Why Continuous Accessibility Is a Strategic Advantage
    Melanie Sumner: Why Continuous Accessibility Is a Strategic AdvantageMelanie 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.codesLinks and ResourcesMelanie's WebsiteHelios Design System at HashiCorpCradle Series by Will WightEmber Community SurveyA11y Automation GitHub ProjectAxe-coreFollow Melanie:GitHubLinkedInThanks 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 PodcastsSpotifyOr search "Maintainable" wherever you stream your podcasts.Keep up to date with the Maintainable Podcast by joining the newsletter.
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  • Joe Masilotti: Simplify Your Stack, Ship Mobile Sooner
    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 MaintainabilityJoe 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 CodebaseJoe outlines his ideal onboarding checklist and how he adapts to unfamiliar environments.[00:08:00] Setting Communication and Collaboration ExpectationsThe three questions Joe asks every client to understand how their team works.[00:13:02] Offering Opinions—Only Where InvitedWhy Joe stays scoped to the work he’s hired for, even when tempted to fix more.[00:14:15] When Technical Debt Enters the ConversationJoe explains how debt discussions usually emerge after version one is shipped.[00:15:33] Who Should Read Hotwire Native for Rails DevelopersJoe describes the type of developer his book is written for and what it covers.[00:18:01] Choosing Native vs. Hybrid for Your Rails AppA framework comparison based on your current frontend architecture.[00:20:00] Introducing the Hotwire Native MindsetWhy logic belongs on the server and the client should stay thin.[00:21:00] Bridge Components: How Rails, iOS, and Android ConnectJoe walks through how native and web technologies pass data between layers.[00:24:00] Why Even a Web View-Based App is Worth ShippingThe practical benefits of discoverability, push notifications, and native APIs.[00:28:01] Replacing Unmaintainable Apps with Hotwire NativeJoe describes how hybrid rewrites often reduce mobile code by 90%.[00:31:33] Letting Go of Feature ParityWhy most clients end up cutting features they originally wanted to preserve.[00:32:18] Scoping and Estimating Project-Based WorkHow Joe uses repeatable patterns to price fixed-fee consulting engagements.[00:35:15] Using AI to Translate Between Tech StacksJoe shares how he leverages LLMs to explore unfamiliar languages like Kotlin.[00:42:26] Long-Term Maintainability and When to Touch the CodeWhy some apps don’t need changes for years—and that’s okay.[00:43:43] Why Hybrid Apps Are Easier to ReplaceJoe explains why hybrid apps are often more disposable and less risky than monolithic web apps.🔗 Resources Mentioned:Joe’s Book: Hotwire Native for Rails DevelopersJoe’s NewsletterHotwire Native Mindset ArticlePlease Unsubscribe, Thanks by Julio Vincent GambutoFollow Joe on X (formerly Twitter) and visit masilotti.com to learn more.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 PodcastsSpotifyOr search "Maintainable" wherever you stream your podcasts.Keep up to date with the Maintainable Podcast by joining the newsletter.
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Over Maintainable

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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