Obvious in Hindsight

A manager once asked me how to think big — how to see beyond the box. It wasn’t coming from a place of doubt; he had been delivering consistently, hitting every goal. That’s what made the question interesting. The better we get at delivering, the harder it becomes to look up. Execution demands focus, and focus narrows vision. Thinking big isn’t about suddenly having visionary ideas; it’s about freeing enough mindspace to notice the ideas already floating around us. That’s the heart of Tenet #5: Think 10×, Build 1× at a Time — stay anchored in delivery while still leaving room for imagination. I told him that a manager still has to deliver. That part never changes. The way to think bigger is to create space without breaking delivery . The easiest path is partnership. Partner with a senior engineer who can lead the technical direction while you look around corners — or free that engineer’s time so they can explore while you keep the ship steady. Either way, two people share the load: o...

I’ve broken more things than I’ve built — and that’s exactly why this blog exists. Over the years, I’ve learned that the most valuable lessons rarely come from perfectly executed plans. They come from the quiet moments after things break — when you realize what you missed, what you assumed, or what you could have communicated better. Most of those insights seem obvious in hindsight. This space, Obvious in Hindsight , is my running log of those realizations — from building reliable systems at scale to learning how people, teams, and code all fail (and recover) in similar ways. I’m writing to understand — out loud. Why I’m Doing This Every engineer I respect shares one thing in common: they remember what they got wrong. Not because they’re proud of the mistake, but because they learned something from it that documentation never could. This blog is where I collect my own version of those reminders — along with some movie quotes. Each post will tie back to one of my core tenets ...