Why AI Coding Made Me More Productive - And Less Happy | Dillon Mulroy

Why did AI coding make Dillon Mulroy more productive and less happy? He stopped writing most of his own code after Claude Opus 4.5. Six months later he ships more than he ever has, still reads every line, and enjoys the work less. The small implementation hits that used to create flow are gone. The day is now one hard design problem after another, and that is more exhausting. Dillon is a principal engineer at Cloudflare. This episode answers what Cloudflare's May layoff of about 1,100 people looked like from inside, why lab-style agent loops are a poor default for most teams, and how he keeps a model on a short leash with Ghostty, Herdr, Pi, and Plannotator. Specs are TypeScript types, call stacks, and tests. Pull requests stay in the 300 to 800 line range. He uses Pi's slash tree instead of sub-agents. Dillon is on X at @dillon_mulroy, GitHub at @dmmulroy, and Twitch at @dillon. https://dillonis.online Why did AI coding make Dillon Mulroy more productive and less happy? He stopped writing most of his own code after Claude Opus 4.5. Six months later he ships more than he ever has, still reads every line, and enjoys the work less. The small implementation hits that used to create flow are gone. The day is now one hard design problem after another, and that is more exhausting. Dillon is a principal engineer at Cloudflare. This episode answers what Cloudflare's May layoff of about 1,100 people looked like from inside, why lab-style agent loops are a poor default for most teams, and how he keeps a model on a short leash with Ghostty, Herdr, Pi, and Plannotator. Specs are TypeScript types, call stacks, and tests. Pull requests stay in the 300 to 800 line range. He uses Pi's slash tree instead of sub-agents. Dillon is on X at @dillon_mulroy, GitHub at @dmmulroy, and Twitch at @dillon. https://dillonis.online Show notes, transcript, and links: https://www.wordman.dev/podcast/dillon-mulroy-i-enjoy-coding-less-than-ever/ Key Takeaways Dillon Mulroy has not written most of his own code since Claude Opus 4.5, from about mid-December 2025 or mid-January 2026. He still reads every line. He is more productive and less happy because the small implementation hits that created flow are gone. The day is one hard design problem after another. A single human still owns the output. Greater reach in less time means more review, not less. Training juniors is the open problem: the struggle that built architecture intuition is easy to skip with a prompt. Cloudflare's May layoff cut about 1,100 people, roughly 20% of the workforce. In his view it was mostly an AI-driven change in which roles exist. They opened different roles the next day. Lab-style agent loops are impractical for a median developer at today's prices. He wants receipts before treating them as the default. Anthropic Fable is a non-starter for a company like Cloudflare, he says, because it does not ship with zero data retention and can drop a session onto Opus 4.8. His stack is Ghostty, Herdr, Pi, and Plannotator. Specs are TypeScript types, call stacks, and tests. Pull requests stay in the 300 to 800 line range. He uses slash tree instead of sub-agents. Chapters 00:00:00 I have not written my own code 00:01:18 From bearish to all-in 00:06:55 Tools do not define the work 00:10:02 I enjoy this work less 00:14:16 Macro problems, no flow state 00:17:38 Feeling junior again 00:19:46 Training the next generation 00:23:34 Cloudflare cut 1,100 people 00:26:12 Roles are compressing 00:34:55 Loops are not for the median dev 00:41:50 Why Fable is a non-starter 00:44:05 Getting the model to write your code 00:46:20 Herdr, Pi, and Plannotator 00:51:20 Specs that look like code 00:52:44 Slash tree instead of sub-agents 01:02:00 A queue he can see coming Mentioned Dillon Mulroy The Next Token Not Holding Back the Ocean (Ethan Niser) The Coming Loop (Armin Ronacher) Cloudflare Artifacts Ghostty Herdr Pi Plannotator Graphite