Essential Complexity
Modernizing high-risk systems in the age of AI.
A bi-weekly letter from Joe Leo.
Every system becomes complex. Not every team learns to navigate that complexity well.
Essential Complexity explores how high-risk software systems evolve — where architecture, data integrity, compliance, and production realities matter.
Topics include:
- When AI meaningfully changes system design — and when it doesn't
- Modernizing legacy systems without breaking revenue
- Architecture decisions under uncertainty
- Tradeoffs that shape long-term system health
All Issues
The Platform Illusion: Why AI Won't Save Incremental Software
Feb 17, 2026The market is pricing architectural courage. Companies that simply 'add AI' to existing products won't survive. The winners will rebuild around it.
The Price of Agency
Feb 02, 2026Both OpenClaw and Gas Town imbue LLMs with an agency that stirs strong emotions. One side expresses wonder at what's now possible. The other expresses fear at potential downsides. Both deserve serious attention.
Creative Ambition's Call to Arms
Jan 19, 2026If we stop bringing new people into the profession, software engineering doesn't evolve, it atrophies. A field that can't regenerate itself doesn't get more efficient; it simply disappears.
Stop Moving Faster and Start Moving Forward
Jan 05, 2026If your team adopts AI and suddenly produces 160% of what they did before, congratulations. You're keeping up. You are not winning.
Get a New Map
Dec 22, 2025We're treating AI like a faster compiler for the same ideas we've always had: ship more features, write more CRUD, reduce headcount. The result? Marginal gains and a ceiling on ambition.
We're Still Catching Up to Global Teams
Dec 08, 2025For the last three years, almost every conversation in the software world has revolved around AI. But after 20 years working inside engineering organizations, the real transformation happened quietly, starting in 2020.