People assume there’s a plan behind how I ended up splitting my year between Michigan, Massachusetts, and Florida. There isn’t. There’s a chronology, and it’s mostly a story about a job, a company, a pandemic, and a family.
How it actually happened
I grew up outside Flint, Michigan. Computers were the thing that came easy to me when plenty of other things didn’t. After high school I spent some time in Chicago, and in 2011 I moved to Boston to become the IT director for a nonprofit that supports individuals with mental and physical disabilities. I built that department from scratch, and it taught me two trades at once: the sysadmin work itself, and the part nobody trains you for, budgets, forecasting, and defending a technology plan to people who answer for every dollar. In 2015, that experience became Boston Managed IT.
Then covid. My wife and I spent nearly two years living and working from a cabin on a lake in the woods of northern Michigan. We went up for a season and stayed, and somewhere in there we admitted we were happier than we expected to be. In 2023, when we decided to move closer to family and start our own, we came back to Michigan for good, with a snowbird’s split: summers here, winters on Florida’s Gulf coast, where the biking and boating don’t stop for January.
And Boston never left the rotation. I’m there about every month, and honestly it’s still home in our hearts. Some cities are like that. You move away and they don’t.
What the split does for the work
Running a Boston IT firm and a Southwest Florida IT firm from Michigan only works if the operation doesn’t depend on me standing in the room. So the businesses run on documentation, monitoring, and process that gets written down instead of remembered. That wasn’t a philosophy. It was a requirement, and it turned out to be good for clients, because a company that runs on written-down process is a company that can prove what it’s doing.
The other reason it works is that the most important part of my job travels well. What I’m best at is translating what a business needs into a technology roadmap, and that starts with listening. In a first meeting I mostly ask questions, usually beginning with the same one: what event, or series of events, led you to start looking for someone like me? Once I understand the why, the rest of the conversation is about pain points and what can actually be done about them. Sometimes we’re the right fit. Sometimes we aren’t. That conversation works the same in a Boston conference room, a Sarasota office, or over a video call from Grand Rapids.
And when a conversation does need a room, I get on a plane. Some things you can only learn at a client’s conference table, and I’ve never pretended otherwise. The point of building companies that don’t need me hovering is that I get to be there for the conversations that matter.
The lake
The cabin is still there, and we still go. It’s our getaway: the place we unplug, step away from the screens, and reconnect with the outdoors. I spend my working life making sure technology behaves, so I protect the one place where I don’t think about it at all. I’ve come to believe that’s part of doing this job well, not a break from it.
So that’s the honest version. Three regions, none of them chosen for marketing reasons, all of them now part of how I work. If you’re a leadership team in Boston, West Michigan, or on the Gulf coast, there’s a good chance I’m nearby more often than you’d guess. And if you’re somewhere else, the way I work was built for that from the start.