A December 2025 Parody It’s the week before Christmas and Peter Gibbons is checking his Fidelity app under his desk. He’s 58. Divorced. Three kids, two in college and one who already graduated. The tuition payments keep him up at night. But it’s the health insurance that keeps him here. After two years of construction … Read more
Three years ago, reasonable leaders like you debated whether AI would meaningfully change software development. That debate is over. The question now isn’t whether AI matters—it’s whether you’ve already waited too long to lead. Here’s what’s happening in boardrooms and executive offsites right now: a pervasive anxiety about being behind, combined with a tendency to … Read more
The word “advanced” has become a safety blanket. When someone requests “advanced AI training,” what they’re really saying is: I want to feel like I’m not behind. It’s a status marker, not a learning objective. If you’re taking the advanced class, you must be advanced. The word does the work of making you feel sophisticated … Read more
If you haven’t seen an agent build software in November 2025, hop on YouTube. The demos are everywhere. AI writes code. AI finds bugs. AI generates tests. You’ve seen it. Your board has seen it. Everyone has seen it. So why are you about to sit through it again? When you schedule a meeting with … Read more
There’s a pattern playing out across enterprises right now. A CxO reads the headlines about AI transforming software development. They call their VP of Engineering. “We need an AI strategy.” Three months later: two piloted tools, significant budget spent, and nothing to show except a handful of engineers who occasionally use autocomplete. The problem isn’t … Read more
I’m sending this link to a friend, who called me today to discuss this issue. Jim isn’t the name, but the problem is real. Jim, Remember when we used to walk the streets of Detroit talking about the buildings? You’d point up at the Guardian Building and go on about the Aztec tile work, how … Read more
I wrote recently about how mid and late-career developers, engineering directors, and VPs of engineering need to rebuild around AI. This is the version for CxOs. Because leading a company through AI transformation is an order of magnitude harder than transforming engineering organizations, and the competition for board seats in 2028 will be brutal. You’ve … Read more
I wrote recently about how mid and late-career developers and engineering directors need to rebuild around AI. This is the version for VPs. Because transforming 200-person engineering organizations is an order of magnitude harder than transforming teams, and the competition for CTO roles in 2028 will be brutal. You’ve worked fifteen, twenty, maybe twenty-five years … Read more
I wrote recently about how mid and late-career developers need to rebuild their careers around AI. This is the version for directors. Because transforming organizations is harder than rebuilding individual technical skills, and the timeline is just as brutal. You’ve worked ten, fifteen, maybe twenty years to get here. You’re good at leading teams. You’ve … Read more
I ran CantonCoders.org, a non-profit that helped over 80 people transition into tech jobs. We never charged a thing. Back then, the path was clear: get a certification or degree, practice interviewing, build a portfolio. It worked. You got a job. That path from 2023 doesn’t exist anymore. And honestly, neither does the path that … Read more