Aaron Held Engineering & craft

The Island of Misfit Toys: Making the Azure Private Link Video

That’s Slonik up there in the storyboard image, a friendly PostgreSQL elephant sitting behind a desk under a neon “OPEN FOR BUSINESS” sign, watching a line of AKS (Azure Kubernetes Service) shipping containers wait their turn at the door. He was going to star in a video about Azure Private Link. He had a co-star, too: Ricky the Raccoon, our hacker, who shows up first in a hard hat with a jackhammer, then in a top hat and monocle, and finally in a fedora and trench coat where he’s figured out how to spin up his own Azure VM and walk straight in through the “Allow public access from any Azure service” checkbox. There was a circus tent, somewhere in Act 2, representing the entirety of Azure’s customer base flooding through that checkbox like a carnival. ...

April 26, 2026 · 8 min · Aaron Held

2026: Year of Community

I spent many hours over the holiday break wrestling with Docker path mappings on my homelab server. Multiple open source apps, each expecting files in slightly different locations. Mount points that worked for one broke another. Environment variables that I had to continually down and up the stack to test. So I did what we all do now: I asked an AI. Ten minutes later, I had it all working. Problem solved. ...

January 1, 2026 · 7 min · Aaron Held

The North Star: Why Engineering Teams Need a Vision to Navigate By

I’ve watched talented engineering teams burn out not from working too hard, but from working without direction. The pattern is always the same: leadership announces a new strategic pivot every quarter, teams scramble to adjust, morale craters, and your best people start updating their LinkedIn profiles. The problem isn’t the changes themselves. It’s that without a guiding vision, every shift feels like a complete reversal rather than a necessary course correction. ...

November 30, 2025 · 7 min · Aaron Held

Why Your Strategic Planning Fails (And How to Fix It)

Why Your Strategic Planning Fails (And How to Fix It) I’ve seen more agile planning sessions derailed by politics than by any technical challenge. It always starts the same way. You get the right people in a room—Product, Engineering, Sales, Finance—and for a moment, it feels like a powerful alliance focused on building the future. A spy’s guide to strategy helped me realize these sessions unfold in three acts: Alliance, Competition, and Endgame. ...

October 25, 2025 · 2 min · Aaron Held

AI Won't Kill the Middle Manager, It Will Free Them

I got into management because I saw myself as a player-coach. I could create software and make my teams more effective. The most rewarding part? Shielding creative people from bad direction and then watching them delivering results. Success gave me more influence to shape process and continue to help my teams be their best. Chris Dixon’s recent, high-profile shift from “Management” back to “Engineer” made me pause. He’s a true champion of the possible who had an outsized impact on my early career, and his move forced me to think about my own direction. ...

October 12, 2025 · 6 min · Aaron Held