Maintainable cover art

Maintainable

Maintainable

By: Robby Russell
Listen for free

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.© 2019-2026 Maintainable Software Podcast Career Success Economics
Episodes
  • Chris Coyier: The Long Game of Maintaining CodePen

    Chris Coyier: The Long Game of Maintaining CodePen
    Jun 16 2026

    What does it take to keep a product healthy after more than 15 years of continuous evolution?

    In this episode, Robby Russell talks with Chris Coyier, co-founder of CodePen, about the long game of maintaining software. Chris shares how CodePen has evolved over time, the trade-offs involved in migrating parts of the platform from Rails to Go, and the challenges of balancing maintenance work with the desire to build what's next.

    They also explore the human side of maintainability, the role of technical debt in shaping priorities, and why small teams often have to make very intentional decisions about where to invest their limited time and attention.

    Whether you're maintaining a side project, stewarding a legacy application, or helping a team navigate change, this conversation offers practical insights into building software that lasts.

    Key Topics
    • Defining what "well-maintained software" really means
    • Why maintainability is often more of a people problem than a code problem
    • The origin story of CodePen
    • Supporting a product that has evolved over 15 years
    • Balancing maintenance work with product evolution
    • Gradually migrating from Rails to Go
    • Using GraphQL across multiple implementations
    • Technical debt and its many interpretations
    • Team size, communication overhead, and organizational design
    • Simplifying software by embracing browser capabilities
    Links & Resources
    • ChrisCoyier.net
    • Chris Coyier on Bluesky
    • CodePen
    • ShopTalk Show
    • CSS-Tricks
    Book Recommendation

    Understanding Comics: The Invisible Art (Goodreads) by Scott McCloud

    Thanks to Our Sponsors!

    Your test coverage says 90%, but that might be misleading. Undercover CI looks at your Ruby pull requests and shows you which parts of your changes weren't tested- not just overall coverage, but what changed and what got missed, down to the method level. Visit undercover-ci.com and use code MAINTAINABLE for 15% off your first billing cycle. Free for public repos. Private repos with unlimited users also available.

    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.
    Show More Show Less
    54 mins
  • Sally Lait: Confidence Is the Real Metric

    Sally Lait: Confidence Is the Real Metric
    May 5 2026
    Sally Lait joins Robby Russell on Maintainable to explore software maintainability through a different lens… not just code quality, but how teams work together over time. Sally is a fractional technology leader and advisor with more than two decades in the industry. You can follow her on LinkedIn or Mastodon. They start with a familiar question: what makes software well maintained? Structure and standards matter, but Sally shifts the focus to signals around the edges… documentation, onboarding speed, knowledge sharing, and especially how confident people feel making changes. That confidence becomes the thread throughout the conversation. Teams with high confidence move faster and adapt more easily. Teams with low confidence hesitate, avoid parts of the system, and struggle to make progress… regardless of what the code looks like. Robby and Sally also dig into why maintenance work often struggles to get traction. It rarely speaks for itself. Leaders need to connect it to outcomes the business already cares about… risk, hiring, delivery speed, and long-term sustainability. Sally references a LeadDev panel she moderated on why maintenance still feels “stuck in 2015”: Why Software Maintenance Is Stuck in 2015. They also discuss modernizing legacy systems and moving away from long-standing in-house software… work that is rarely just technical. It requires trust, clear communication, and navigating the emotional attachment teams have to what they’ve built. The episode closes with advice for engineers joining older codebases: stay curious, build relationships early, and use onboarding gaps as opportunities to improve things for the next person. Episode Highlights [00:01:02] What Makes Software Maintainable: Technical quality matters, but cultural signals often tell the deeper story. [00:05:45] Why Progress Still Feels Slow: Even with improvements, teams can feel stuck due to perception gaps. [00:07:30] Communicating Small Wins: Lack of visibility into incremental progress impacts morale and confidence. [00:12:40] Influencing Without Manipulating: Maintenance work needs to be framed in business terms. [00:16:00] Technical Debt as a Hiring Problem: Outdated systems affect recruiting and retention. [00:20:22] Modernizing a Siloed System: Unlocking legacy data required both technical and organizational change. [00:26:55] Building Trust for Change: Surprise proposals fail… alignment takes time. [00:32:39] Letting Go of “Our Baby”: Replacing systems involves emotional and cultural dynamics. [00:46:25] Joining an Older Codebase: Practical advice for onboarding and building confidence quickly. Resources Mentioned Sally LaitSally Lait on LinkedInSally Lait on MastodonWhy Software Maintenance Is Stuck in 2015 (LeadDev Panel)Lara HoganThe Murderbot Diaries by Martha WellsDeath of the Author by Nnedi OkoraforSally’s Reading & Reviews Site Thanks to Our Sponsors! Your test coverage says 90%, but that might be misleading. Undercover CI looks at your Ruby pull requests and shows you which parts of your changes weren't tested- not just overall coverage, but what changed and what got missed, down to the method level. Visit undercover-ci.com and use code MAINTAINABLE for 15% off your first billing cycle. Free for public repos. Private repos with unlimited users also available. 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.
    Show More Show Less
    56 mins
  • Rein Henrichs: The Real Work of Maintenance Happens Before You Touch the Code

    Rein Henrichs: The Real Work of Maintenance Happens Before You Touch the Code
    Apr 14 2026
    Software maintenance is often framed as a technical problem. Refactoring code, fixing bugs, or upgrading dependencies. In this conversation, Robby Russell talks with Rein Henrichs about a different lens, one centered on understanding. Rein is a Principal Software Engineer at Procore, where he works within a large, long-lived system used across the construction industry. Rather than focusing on tooling, Rein emphasizes that well-maintained software is software that makes sense to the people maintaining it. To explain this, Rein introduces the idea of the line of representation, drawing on the work of Richard Cook. Engineers do not interact directly with systems. They rely on representations such as logs, dashboards, and code. These are approximations, not reality, echoing ideas from Plato’s Allegory of the Cave. When those representations break down, teams lose shared understanding, what Rein describes as “common ground.” This often shows up as weak signals. Subtle indicators that something is not quite right. They are easy to ignore, but over time they lead to confusion and slower decision-making. Incidents make this especially visible. Rein explains how teams build alignment under pressure, highlighting that the role of an incident commander is coordination, not control. Clear communication matters as much as technical correctness. The conversation also explores how large systems behave in practice. They rarely fail completely. Instead, they degrade in multiple ways at once. While SLOs can help teams respond to customer-facing issues, they do not capture internal clarity or alignment. Rein references W. Edwards Deming to highlight a common trap. Not everything that matters can be measured. High-performing teams often rely on judgment, experience, and shared context. Toward the end, Rein connects these ideas to The Field Guide to Understanding Human Error by Sidney Dekker, challenging the idea that incidents are simply caused by mistakes. Instead, they emerge from the same behaviors that usually lead to success, just under different conditions. For teams working in complex systems, the takeaway is straightforward. Maintaining software depends on maintaining understanding. Links & Resources ProcoreRein Henrichs on LinkedIn Concepts & References How Complex Systems Fail – Richard CookThe Field Guide to Understanding Human Error – Sidney DekkerW. Edwards DemingGerald Weinberg – Secrets of Consulting Referenced in this Conversation Kent Beck: You’re Ignoring Optionality and Paying for ItCharity Majors: Deploys Are Just the BeginningHeidi Helfand: The Art and Wisdom of Changing Teams 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.
    Show More Show Less
    55 mins
adbl_web_anon_alc_button_suppression_t1
No reviews yet