It Started With a Box of Wine
It was a box. I want to be upfront about that. Not a bottle — a box. We were sitting on the balcony of our 21st-floor apartment watching the sun do that thing it does over Tampa Bay, where it just melts into the water like it has nowhere better to be. It’s the kind of view that makes you feel like your life is going pretty well.
And it was. That’s the thing. Our life was genuinely, measurably going well.
Somewhere around glass three (okay, four), Dylan said it out loud for the first time:
“What if we just… lived and ran the business on the road?”
I didn’t immediately open a spreadsheet. Which, if you know me, tells you something about how the wine was hitting. But I also didn’t say no.
The Problem With Everything Being Fine
Here’s what our life in downtown Tampa looked like: a beautiful apartment above a Mediterranean restaurant, a wine shop, a plant store, and an ice cream shop. Our agency, Squid X Media, was growing. Verde and Quinn were installed on their respective couch cushions like they owned the place, which, let’s be honest, they do.
Everything was good. And that was sort of the problem.
Not because good is bad — good is great, good is the goal. But comfort has a way of making you very convincing to yourself. You start filing things under “someday.” After the next milestone. After things slow down. After we’re retired and sixty-five and the dogs are…
Well. That’s the part that crept into the conversation on the balcony that night. The someday logic only works if you have unlimited somedays. We’d been learning, slowly and then all at once, that you don’t.
We weren’t unhappy. We weren’t running from anything. We had built something we were proud of and a life that could, theoretically, be picked up and moved. So the question became: if not now, what exactly are we waiting for?
The Research Spiral (I Made a Spreadsheet)
Within a week, I had a spreadsheet. Dylan had YouTube. Together, we had a problem.
We watched hundreds of videos from people who were already doing exactly what we were considering — couples, solo travelers, full families, people with dogs. We took notes on trailer specs, campground memberships, solar setups, Starlink reliability, dog-friendly policies at state parks. The research was supposed to make us more certain. It mostly just made us want to research more.
What actually helped was when we stopped asking “is this possible” and started asking “what do we actually need.” Those are different questions with very different answers. The first one sends you toward 21-foot floor plans with separate bedrooms. The second one brings you back to 13 feet.
(13.7, as Dylan will remind you if given any opportunity at all.)
What We’re Actually Doing
We’re hitting the road in June with a custom-built Escape 13ft trailer, two pittie mixes, and a marketing agency we’ll be running on Starlink from wherever we happen to be parked.
Less square footage, more time zones. Less doomscrolling, more board games and paperbacks. Less “we should really do that someday” and more just… doing it.
We are not people who had a dramatic falling-out with our old life. We liked our old life. We’re just choosing a different one for a while, because we built a business that lets us, and because Verde is 14 years old and the only timeline that matters is the one in front of us.
That’s the whole origin story. A box of wine, a good view, and a question that turned out to be easier to answer than we expected.
FOLLOW ALONG + WHAT’S NEXT
We’re documenting all of it — the prep, the chaos, the dogs, the work-from-the-road logistics — on Instagram and TikTok at @TheLongWayLiving.
✨Coming next: How we chose the Escape 13ft (and why we almost bought something twice the size) →