People ask me all the time what it was like to walk away from a 14-year career in corporate to build something from scratch. I’ve tried to answer that question a hundred different ways. Whether it’s with numbers, timelines, or stories about pitches and investors and/or lease signings. But the answer that feels most true is not any of those things but a picture that formed in my head early in the process and has stayed with me ever since.
Imagine you have been living on an island your whole adult life. The island is good. Really good. You have a system that works, a community that knows you, and a level of comfort that took years to build. You know where everything is. You know how everything works. Life on the island has its challenges but it is yours and it is familiar and it provides everything you were told you were supposed to want.
Then one day you hear about another island.
You can’t see it from where you are standing. You look out at the water and there’s nothing on the horizon. Just open ocean as far as you can see but something tells you it’s out there. A direction without a destination and once you hear about it you can’t stop thinking about it. You start asking questions nobody around you can answer because nobody around you has made the swim.
The Decision
For a long time I stood at the water’s edge and looked out. I had built something real in corporate. Fourteen years at CDW and Gartner. Portfolios built from zero to millions. Executive relationships, complex deals, and a network that took a decade to develop. The island was not a bad place. I want to be clear about that. I’m grateful for everything it gave me but I kept looking out at the water and the pull kept getting stronger. The question stopped being whether I wanted to make the swim and started being whether I was willing to and in 2025, I decided I was. I left Gartner and went all in on building HUMN.
The Swim
What nobody tells you about leaving the island is what happens after you enter the water.
At first it’s electric. The people on your island cheer you on. Everyone is at the shore. The energy is high and the belief feels collective and you are moving and that momentum carries you through the early days. But as you swim further out something starts to happen. The cheering fades. The voices get quieter. You look back and the shore is getting smaller. You look forward and the other island is still not visible. You are in open ocean. The water gets deeper, darker, colder, and very, very quiet.
I feel like this is the part nobody talks about. Not because they want to hide it but because it’s hard to describe to someone who hasn’t felt it. The loneliness of the middle distance. The place where you are too far from the old island to go back and not close enough to the new one to feel certain it exists. This is where most people turn around. Not because they lack courage or capability but because the middle distance is genuinely hard and the shore behind you is genuinely familiar.
But I kept telling myself, “Keep swimming.”
Not because I was fearless because I’m not. Not because I had a perfect plan because I didn’t. I kept swimming because turning around felt like a betrayal of something I couldn’t name but couldn’t ignore. I kept swimming because every time I considered going back I thought about the version of myself at 70 years old asking “What if?” I kept swimming because the pull toward the other island was stronger than the pull toward comfort.
The Other Island
I can see it now.
It’s been almost 20 months since I left corporate and the other island is no longer a direction without a destination. It’s a lease at 1675 Broadway in downtown Denver. It’s a design package and a permit submission and walls that are about to come down. It’s an advisory board that flew across the country to spend a full day building something together. It’s investors who said yes before there was much to say yes to. It’s a community that wanted to become the foundation of something much larger.
I’m not fully settled on the island yet. The doors aren’t open yet. The members aren’t walking through yet. The full vision is still being built. I’m on the island but I’m rebuilding everything I had on the previous island and that takes time. But now that I can feel the ground, it changes everything about how I think about the next chapter of my life.
What It Actually Feels Like
So what does leaving corporate actually feel like?
It feels like standing at the water’s edge for a long time before you jump. It feels like the most electric decision you have ever made followed immediately by the most uncertain period of your life. It feels like the cheering fading as you swim further from everything familiar. It feels like the middle distance, cold and quiet and longer than you expected. But… If you keep going, it starts to feel like the most important thing you have ever done.
Take the risk.
