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, simplicity over perfection (Worse is Better), complexity management, quality-speed tradeoffs, and career positioning. Each essay is accompanied by personal lessons learned and practical applications, emphasizing pragmatism, simplicity, and business value over technical perfectionism.

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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.