Change has never been something I'm a fan of. I like systems, I like knowing what Tuesday looks like before Tuesday shows up, and I've spent most of my career building structure for other people's organizations precisely because I value it so much in my own life. This year decided none of that mattered. In the span of a few months I left a job I'd fought hard to get, left the only house I'd called mine in a decade, and somehow ended up starting a second company in the middle of a move I was supposed to be focused on. None of it was planned. All of it turned out right.
Leaving the Job I Was Supposed to Want
I left a CEO seat. Not because the work stopped mattering to me, it never has, but because I'd reached the point where staying meant agreeing to run an organization the way it had always been run instead of the way it needed to run going forward. I'd been running Gail Consulting Group as a side hustle since 2021, nights and weekends, while I kept the steady paycheck and the title. Two months ago I bet on myself and went all in on it full time. Trading that steady paycheck for a business with my name on the door is the kind of decision people warn you against at every dinner party you go to. I did it anyway. Still the best professional decision I've made.
Leaving the House
Then there was the house. Ten years in one place builds up more than you realize until you start packing it into boxes. I moved out to move in with my girlfriend, Ciarra, about a mile down the road, which sounds simple until you're the one boxing up a decade of accumulated life with someone who gets genuinely, dangerously hangry if a move runs through a meal. (Feed her. I cannot stress this enough.) We hired pros for the couch and the heavy stuff. Everything else, the closets, the kitchen, the years of stuff you forgot you owned, came down to the two of us, a stack of cardboard boxes that kept giving out at the bottom, and more patience than either of us knew we had.
The Company We Didn't Plan On
Somewhere around box two hundred we grabbed some plastic totes that happened to be on sale instead of buying more cardboard. Stackable, lockable, actually held their shape. The rest of the move went easier than either of us expected, and that should have been the end of it. Instead, elbow deep in totes, my business brain kicked into gear and refused to shut back off. If a few totes made our move easier, other people moving around Winchester and the Northern Shenandoah Valley probably needed the same thing. There are companies doing tote rentals well closer to DC. Nobody does it out here. So for the rest of the move, Ciarra and I packed two things at once: a house and a business plan.
That business is Old Town Totes. We deliver clean, stackable totes to your door, you pack them, we pick them up when you're done, and you never end up with a garage full of plastic bins after. Old Town is what Winchester's downtown has always been called locally, and Ciarra and I are both Winchester natives, so the name fit before we even had to go looking for one. We're opening for bookings July 1, serving Winchester and the Northern Shenandoah Valley. If you're moving in that area this summer, email me and I'll make sure you hear about it first.
I still don't love change. I don't think I ever will, and I'm not going to pretend the last few months felt comfortable while they were happening. But the job, the house, and the company sitting in front of me right now all came from change I didn't ask for and very nearly talked myself out of. Maybe that's the only real lesson in any of this: the change you're dreading is sometimes just the good idea that hasn't introduced itself yet.
