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

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

Streamlining Blog Writing with Claude Code: My Complete Workflow

Introduction For over 25 years, I’ve blogged through countless iterations of my writing and technical processes. Recently, I’ve found something that makes writing enjoyable again: Claude Code. This isn’t another “AI will replace writers” story. It’s about how AI can enhance creative expression by handling the tedious parts of content creation. Crucially, it helps me overcome the final hurdle: actually publishing. Most of my posts start as first drafts that never see the light of day. Now, my Robot Buddy guides me through the entire process, from idea to execution. In this post, I’ll walk you through my complete workflow from initial idea to published post, showing exactly how Claude Code integrates with Hugo, my static site generator of choice. You’ll see real screenshots, actual commands, and the genuine collaborative process that happens when human insight meets AI assistance. ...

September 6, 2025 · 17 min · Aaron Held

Agile vs Economic Downturns

Is the Economy derailing your Agile Transformations? Economic uncertainty hits. Layoffs are all over the news and productivity suffers. Every time, I see people wanting to blame the loss or productivity on budget cuts and layoffs. That is the short term impact, but I see longer term harm playing out. Teams that were thriving on collaborative decision-making suddenly go quiet. The same people who were debating sprint priorities and pushing back on requirements start waiting for marching orders from above. ...

September 5, 2025 · 4 min · Aaron Held