In this episode of the Maintainable Software Podcast, Robby sits down with Cassidy Williams, Developer Advocate at GitHub, to explore the dynamic nature of a tech career, the delicate balance between clever code and maintainability, and the evolving trends in software development.

Cassidy begins by discussing what makes software truly maintainable—starting with the ease of onboarding for new developers. She emphasizes the importance of clear documentation and warns against the pitfalls of writing overly clever code that might be difficult to maintain in the future.

They then delve into the challenges of joining an existing codebase and managing technical debt. Cassidy shares her experiences, noting how codebases often start pristine but become more cumbersome as projects evolve and pivot.

The Importance of Onboarding: Cassidy explains how fast someone can jump in and start working on code as a key indicator of well-maintained software.

[00:10:21] Balancing Cleverness and Maintainability: Cassidy elaborates on why writing clever code can be a double-edged sword when it comes to long-term maintainability.

[00:16:00] Navigating Career Pivots: Cassidy reflects on her own career journey, likening it to a "career jungle gym" where paths are non-linear and require thoughtful decision-making.

[00:18:36] Working at Netlify: Cassidy shares her experience with upgrading a router within an existing codebase, highlighting the importance of collaboration and bringing in external expertise.

[00:24:00] Local-First Software: Robby and Cassidy explore the trend of local-first software, emphasizing the benefits of data ownership and the ability to work offline.

[00:26:30] Developer Wishlists: Cassidy suggests creating personal and communal wishlists for addressing technical debt, fostering a collaborative approach to maintaining software.

[00:31:50] Jumbile - Cassidy's Side Project: Cassidy introduces her word game, Jumbile, detailing its development process and the unique challenges she faced.

Cassidy also discusses her love for Brandon Sanderson's books, specifically the Mistborn trilogy, and the importance of owning your data in today’s digital landscape.

Key Takeaways:

Maintainable software allows new developers to quickly contribute, thanks to clear documentation and readable code.
Clever code can be a joy to write but may lead to maintenance challenges down the line.
A career in tech often resembles a jungle gym, requiring flexibility and thoughtful navigation.
Involving open-source maintainers in large codebase changes can provide invaluable insights and streamline the process.
Local-first software is gaining traction, offering benefits in data ownership and offline functionality.

Resources Mentioned:

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Cassidy Williams: Navigating the Career Jungle Gym in Tech

Maintainable