All Posts

I was thinking recently about a time in my career when everything felt in flow. Not just for me, but for the entire product organization. We weren't necessarily working longer hours. We weren't using some revolutionary methodology. We weren't even particularly well-resourced. But something was fundamentally different. I had theories about what made that period special, but I wanted to test my assumptions. So I reached out to colleagues from that time and asked them: What do y

About Zenblen Zenblen is a startup based out of Chicago that has engineered a beautifully designed automated smoothie kiosk, complete with technologically impressive onboard systems for blending and vending, and a 32-inch touch screen display. Their kiosks are loved throughout the universities, hospitals, and office buildings where they're deployed across the city of Chicago. The Challenge Zenblen's infrastructure had grown organically. Core resources like the database and co

When I suggested this article topic to my engineering partners here, they bristled. Good. That tension is exactly why we need to have this conversation. They were concerned that I was pushing back on the need for technical investment work. I wasn't. I was pushing back on the lack of precision in how we talk about it. And that distinction matters. The Problem with "Tech Debt" A few years ago I was helping a team that was battling incident after incident. Each outage expanded t

A Battle-Tested Playbook for Migrating Critical E-Commerce Functionality from Monolith to Microservices Migrating major functionality out of a monolith is like swimming against a relentless current. The gravitational pull of tightly coupled systems, undocumented business logic, and years of accumulated requirements makes every extraction feel like light trying to escape a black hole. Yet here we are, on the other side, with a playbook that transforms high-stakes releases into