Three years ago this weekend, we packed up Boston and moved to Tampa.
In Boston, I had two decades of reputation. People knew my name in the window covering world. Referrals came in without me chasing them. I had built a local presence the slow way—one job, one handshake, one five-star review at a time.
I assumed I’d hit the ground running in Tampa. New market, same hustle.
It doesn’t work like that. Yeah, an online presence helps. But not as fast as you need.
Becoming “known” in a new city takes years, not months. The phone doesn’t ring just because you showed up. The relationships have to be rebuilt from zero—and you don’t get to skip the awkward early innings just because you have experience.
That part was humbling. Some days it still is.
It’s relaunching a business 2.0. You know how it works and where you want to go. Yet, the bills don’t wait until you are settled in.
Then the hurricanes came.
We had just bought a house when the storms rolled through. What should have been a fresh start turned into longer than a year of delays, repairs, insurance calls, and contractors running on Florida time.
In one way, it was a gift. We got to rebuild parts of the house the way we actually wanted. In another way, it set us back way too long.
That’s the part nobody tells you about big moves: the universe doesn’t pause to let you get comfortable. Life keeps swinging, and you have to keep your footing on ground you don’t fully know yet.
So did I regret moving South?
Not a single bit.
Because every time I come home after a hard day—and there have been plenty—and I see the sun still up at 7 p.m. in February, something in me exhales.
That’s the part I didn’t expect. I knew I wanted warmer weather. I didn’t know how much that simple thing—daylight after work—would do for me. It’s not just the climate. It’s a kind of permission to be a human being instead of a worker bee.
Being home shirtless and in flip flops is something money can’t buy.
Tampa gave me that. Boston never could.
Now here’s the part I want to be careful about.
I’m not writing this to convince you to move.
Boston gave me things Tampa never will. Higher-paying work. A faster business culture. A grittier, more relentless energy that absolutely sharpened me into who I am. If you thrive in that environment, leaving might be the wrong call.
Tampa is more relaxed. The trade-off is real—you give up some of the financial ceiling for a slower pace and a different quality of life. That math works for me. It might not work for you.
Here’s the irony: the common misconception is that “Florida is a cheap place to live.” That cannot be farther from the truth. Insurance is REALLY REALLY expensive here. Cost of living is not what it used to be either. In reality, you work more to just break even. It worked for me because I built a safety net. But the struggle is real if you are not financially prepared.
A new zip code won’t fix what isn’t working. It won’t make you more disciplined, more confident, or more successful. It just changes the backdrop.
What it can do is reveal what you actually want—once the old comforts and old routines aren’t there to lean on anymore.
Just because someone is wildly successful selling ice cream cones doesn’t mean you’ll be too. Their recipe isn’t your recipe.
We all may have the same goal in life: be happy, healthy, and able to do whatever puts a smile on our faces. But the truth is, what makes me happy isn’t exactly what makes you happy.
So, do your due diligence before you get too excited:
- Do you have the financials to support your new chapter?
- Can you continue your professional pathway where you’re going?
- Are you interested in pressing on the gas pedal, or are you ready to slow down?
That’s what three years in Tampa has taught me.
Courage isn’t always loud. Sometimes it looks like a U-Haul pulling out of a driveway on Memorial Day weekend.
But courage by itself isn’t enough. You also need patience. The kind that lets you sit in the awkward middle while the new life slowly becomes yours.
“Nobody Told Me That” – Upcoming Book
This is exactly the kind of story I’ve been collecting for the book I’m working on—Nobody Told Me That. The Tampa move belongs in what I call the “Courage in Motion” bucket: the early, sweaty, uncertain side of bravery, long before success has a name tag.
More on the book soon. For now, back to the question I keep asking myself—and the one I’d ask you:
If you’re thinking about a big move—a city, a career, a relationship, a chapter—I’d just ask you this:
Are you running toward something? Or running away from something?
The first one usually works out. The second one usually follows you.
Warmly,
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