A new term has been making the rounds, one anybody who has been using agents to do any serious work over the past year will immediately understand: Cognitive Debt. "...by weeks 7 or 8, one team hit a wall. They could no longer make even simple changes without breaking
Creating a (buzzword warning 🤢) "AI-Native" workspace without touching existing stuff or giving a fully autonomous agent unhinged access. A few weeks ago, I sat down to help show our Head of Product how he could use Claude Code for... Not Code. I gave the usual rant about how
Have you ever seen one of those YouTube videos from some 21 year old day trader standing in front of a (rented) lambo, selling you a course on how to become rich? Have you ever asked yourself, "if they are so rich from day trading, why are they selling
So it's the year of our Lord 2026 and you've decided you procrastinated understanding how AI is going to change your career as a software engineer for too long. Now you want to learn to vibe code or vibe engineer or whatever people are calling it
At a work offsite in mid-2023 I gave a talk to the engineering team about how AI was already changing coding. I advised that, like all change in the industry before it, there was no reason to be afraid, but you need to stay on the board and ride the
And Learning to Love “Legacy” Systems Antifragility has been an incredibly important idea to me over the past year. It has deeply influenced how I think about things ranging from my career, to my finances, to my relationships with loved ones, myself, and my spirituality. To me, the value behind
Our highest priority is to satisfy the customer through early and continuous delivery of valuable software. — First Principle of the Agile Manifesto Breaking up work into small chunks and continuously integrating them back together is an energizing way to work. The smaller batches help make changes with reduced risk and
Big Changes Are Fragile Big changes carry more risk than small changes. Ambitious, “big bang” style changes often fail, or generate more organizational ill-will than they do business value. There’s a reason just whispering the word refactor can send a Product Manager into a fugue state. Merging and deploying
A Black Swan is an unpredictable event—a massive shock to our systems. Things that are fragile do not like change. Change hurts. Chaos, volatility, randomness, entropy, the unknown, time—all involve friction and forces that pull at the seams, threatening to destroy the fragile. Sometimes the destruction is abrupt
This morning I rested my chin on the sill of the open window as I showered. The lights were off and the only illumination came from the soft warm glow of the early sun rising over the distant mountains, filtered through the trees. Gazing aimlessly into the backyard through the
I’ve been thinking a lot about change of late. At work, I’m always thinking about change: how to communicate about changes, how to plan changes, and how to implement change. The last few years for me have been a fraught with major personal life changes. Socially… Well, it
A few months ago I had a moment of existential crisis. We were remodeling our basement bathroom and wanted the toilet moved. The contractors came, jackhammered the cement, and laid new pipes. I got home from work and wanted to see the progress, so I poked my head in and