10 software essays that changed how I think

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A curated collection of 10 influential software engineering essays spanning 1989-2022, covering technology selection (Choose Boring Technology), type safety (Parse Don't Validate), refactoring strategy (never rewrite from scratch), monolith vs microservices architecture, team process health (Joel Test), API design principles,

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Dec 18, 2025•25m read time• From newsletter.techworld-with-milan.com

Table of contents

GitHub Actions analytics - what’s actually happening (Sponsored)1. Choose Boring Technology (2015) by Dan McKinley 🔗2. Parse, Don’t Validate (2019) by Alexis King 🔗3. Things You Should Never Do, Part I (2000) by Joel Spolsky 🔗4. The Majestic Monolith (2016) by David Heinemeier Hansson (DHH) 🔗5. The Joel Test (2000) by Joel Spolsky 🔗6. How to Design a Good API and Why It Matters (2007) by Joshua Bloch 🔗7. The Rise of “Worse is Better” (1989) by Richard P. Gabriel 🔗8. The Grug Brained Developer (2022) by Carson Gross 🔗9. Software Quality at Top Speed (1996) by Steve McConnell 🔗10. Don’t Call Yourself a Programmer (2011) by Patrick McKenzie 🔗11. Bonus: How To Become a Better Programmer by Not Programming (2007) by Jeff Atwood 🔗12. Conclusion 📰 What I read daily (you can subscribe to it too!)More ways I can help you Want to advertise in Tech World With Milan? 📰Love Tech World With Milan Newsletter? Tell your friends and get rewards.