There is a specific kind of quiet I have been thinking about lately. It is late. The office is empty, or the house is finally asleep. There is a problem on the screen that refuses to be solved, and for once there is nothing else. No Slack. No calendar invite. No one asking for an…
Category: AI software engineering
Rails + RubyLLM vs LangChain in 2026: The Honest CTO Comparison
The Email That Started This Post A friend who is a founder sent me a Telegram message last month. “We’re three engineers. We have an AI feature to ship by Q3. Everyone says Python. Should I just give up on Rails?” He had a working Rails 8 app. Auth done. Billing done. Three years of…
The Middle Loop Is Where Engineering Actually Lives Now
Someone finally named the thing. There’s a word now for the work I’ve been doing for the last two years without a vocabulary for it. The middle loop. Supervisory engineering. The thing that sits between writing code and shipping it. The thing that didn’t exist before agents started producing code faster than any human could…
Everyone Is an “Engineer” Now, and Nobody Knows What Anyone Does
A CTO’s field guide to the 2026 AI job title theater, with a companion reference guide covering all 40 roles. I have been a CTO for most of my adult life. I have hired, fired, onboarded, mentored, and occasionally been forced to explain to finance why a “Senior Applied Generative AI Engineer II” and a…