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.

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

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