Florida Man Teaches Me A Lesson

July 29, 2021

Jarring. Unsettling. Depressing. As we pulled out of the Tampa airport rental garage and onto the baking, chaotic, 8 lane Sprawlandia thoroughfare, those were the feelings churning in my stomach. Dismal to say the least – considering just 24 hours earlier, I woke up to a thick fog rolling up the St. Lawrence Seaway, obscuring our view of Canada from our window. 

My family does a big trip every second summer, and this year, my sister rented an island in the Thousand Islands region of New York. The place was magical. Built in the 60’s by a local businessman, he poured his heart, and money, into the place. Like everything in the area, the house was built with timber and stone and some serious craftsmanship. It took us two boat trips to haul over our people, luggage and supplies for the week long trip. It was a hard to imagine what it must have taken to build the place, considering all the workers, timber, stone, appliances, etc, had to travel 10 miles by boat.

Being in the house made me feel as if I were getting to experience the history of a family I wasn’t actually a part of. It made me feel like I belonged and I was nostalgic for those endless summers spent in the 70’s and 80’s on the island with the family of the builder. Photos of kids fishing, of the outdoor table spilling over with food from the grill, of big parties with people coming over from adjacent islands, and photos of a father who was successful in building the most special place to soak up every last second of summer with the ones he loved the most. 

The house may have only stood for 60 some summers, but even as an ephemeral occupant, its personal history seeped into my own consciousness. I couldn’t help but feel the surroundings deeply. Us 18 inhabitants were brought closer together by the island and by the house. The place was doing exactly what it intended to do. It was doing what it was designed to do. It was bringing a family closer, it was making everyone happy, it was providing us all with the joy of simple pleasures and beauty. 

The house was sited towards the setting sunand big picture windows framed it perfectly. A terrace sat outside the living room and above a jagged drop off to the water. Rarely in my beer games career have I given much thought to the setting of a game of bocce or cornhole, but it was hard not to notice the glimmering late afternoon sun off the water as I drunkenly sent a bag careening off the back edge of the board for another squandered opportunity to even things up. 

While it may not have been all that old, the house was permanent. It had the patina of being loved hard and shared well. It was obvious some maintenance was being deferred and the place had seen better days, but surroundings don’t have to be immaculate to be special. They have to be lovable. Even sharing the shower with a spider the size of a chihuahua didn’t dampen my attachment. We took turns soaping one another up. 

As the rental boat rounded the breakwater, I waved goodbye to all my favorite people, all gathered in one of my absolute favorite places. It was hard to leave early, but as a consultant, it’s wise to take a job when they come. This 8 acre island provided us with family memories that will be cherished and retold for decades to come. My kids will tell their kids about the island olympics, in which three generations combined on 4 teams to compete in 10 events.


The drive from Tampa to our destination was a little over 30 miles. So I replayed scenes from previous days in my head – fishing, poker, swimming, volleyball, and -in with the terror only a parent can know, watching my daughter launch herself off a cliff as she screamed with joy falling through space until she splashed down into the crisp cold water of the St. Lawrence. This was how I distracted myself.


The setting was soul crushing. Ruthless and unforgiving. Imagine Death Valley, but packed full of Dollar Generals. Every road is wide enough to land two jumbo jets simultaneously. There are no trees, just parking and strip malls all the way to the sea. It’s like a repeating pattern. Once you pass the Lowes, you know Publix will be next, followed by Target, followed by CVS, followed by the Dollar Tree, with a sprinkle of local boating equipment tossed in for good measure. Leaving one road for another, doesn’t bring about any change. The road isn’t any narrower, the pattern doesn’t stop repeating, its as if Willy Wonka partnered up with a strip mall developer to test the very limits of my mental health. 


I am in Florida to speak at a conference with a couple of colleagues. I appreciate the opportunity and am always thankful for anyone that anyone is willing to listen to me. But man, Florida is hard. So much of it is devoid of the things I deem important. Until one actually leaves the land on which Florida sits, and can look back at it from safe distance from sea, it’s hard to appreciate. It’s sprawling beyond belief. It stretches the very mind to comprehend this much sprawl. I can’t understand where all the money comes from to build this much shit. Florida developers could have rebuilt the great wall of China 9 times over, but instead invested in more TGIFridays. 

The rollercoaster of consumerism crap doesn’t stop until we reach our destination. A cute, quaint little downtown. An island of appealing aesthetics in a sea of parking depression. I can’t believe it! This area is attractive and its walkable. It is the antidote to the last hour of suffering. We get out of the car and stroll around under the shade trees. We stop for tacos and catch up on our work at a cool little coffee shop. It feels nice. It actually feels lovable and welcoming. I am forced to reckon with my belief that all of Florida is terrible. I don’t care to reexamine my preconceived notions, but I will if I must. 

Ben, Bernice and I put on the Downtown Happy Hour event on the first day. We throw back a  couple of beers and discuss the downtown issues that irritate us the most. It’s possible have fun discussing zoning and parking if you can believe it. This is followed up by some great questions from the audience. We answer as many as we can before getting kicked out of the theater. The following morning, we host another session on preservation and again, field as many questions as possible. 

The questions are amazing. They are difficult, they are challenging and they push us to dig deeper. The crowd is engaged and wonderful and more than anything, passionate about what they do. I was dreading my visit to Florida, and still have the rage of a thousand college football fans towards all the sprawl, but prior to my visit, I was overlooking something that matters so much. Even in Florida, there are people that are concerned with place. There are pockets of populations that want to see their surroundings improve. This is true everywhere and I allowed my ignorance and arrogance blind me to it. 

More so, I give the people working in preservation and revitalization in Florida all the credit in the world, because they are doing it in the hardest state in the union. They are pushing a boulder that would make Sisyphus call for a T.O. 

Florida is mostly awful, don’t get me wrong. On the whole, the state continues to make choices that leaves resident living in an endless wasteland of concrete misery. The built environment, which is about the only environment one gets to experience in Florida, was built with the sole purpose of ridding residents of their dollars in the cheapest fashion possible. To build in a manner that doesn’t elevate anyone and instead, forces people to feel ugly, cheap, disconnected, and debased is a pathetic choice and one that residents are forced to suffer every day. 

I know my surroundings dictate how I feel, I understand the importance of how we choose to build and the consequences of not taking those decisions more serious. Tales of “Florida Man”should not surprise any of us. A place devoid of permanence and beauty, is going to foster generations of people that aren’t attached and have no connection to their place. “Florida Man” is the most likely outcome for the environments they have created. If I grew up in the shadow of 30 lane highway and the McDonald arch was the only architecture I experienced, I would be “Florida Man” as well. It’s a wiseass comment, but the point is true. There is a steep cost to the type of development Florida is perpetuating, and it is the the health of its citizens. It’s the sanity of the state and the wellbeing of the populace. The outcomes Florida municipalities are propagating in building lifeless, bland and meaningless landscapes are people that are adapting to those very surroundings. Why should anything matter when none of your surroundings matter? Why care about people when your setting has ensured you never interact with them? Why give a shit if you never see anything worth giving a shit about?

But this is only half of the Florida story and that was the half I was expecting. I had some things wrong. It’s good to be surprised. What got me, is that even in Florida, people care. Of course they do, and I am an asshole for not considering it. While most have been beaten down by these lifeless vistas, some continue to resist, and my sweat soaked hat goes off to them. Their challenges are greater than the rest of ours. Their obstacles are superior. To decide to try and preserve and revitalize your community in Florida is tantamount to eating an enjoyable meal with a gluten objector as your date.

My takeaway is this. Florida is a tough place to work if you care about your surroundings. Tougher than most. The uphill battle in Florida looks a lot like a wall. But aren’t we all fighting this battle? Don’t we all deserve to live in places that provide us with some dignity? Shouldn’t we all have a chance to have our community make us proud? Floridians are no different in this and I had not given enough consideration to their plight. 

I won’t give elected officials in Florida a pass for the sprawling debacle they have created, but I will, with my ego in check and a bit humbled, happily acknowledge, the incredible, difficult, likely thankless work, being carried out by all the dedicated and passionate people working to improve their communities. 

These yeoman of preservation and revitalization deserve all the credit for their work. They are pushing back against these overwhelming forces because they know, their neighbors and friends deserve something better. They understand that another Wal-Mart isn’t the solution, but is in fact, the problem. My admiration goes out to everyone in Florida that is working to turn the tide and doing their utmost to preserve the special places that remain; to those working tirelessly to try and elevate their surroundings and give people places they can be proud of.


I left the Thousand Islands with a pit in my stomach for what I was expecting to find in Florida. On the flight home, I was reeling a bit from the experience and feeling pretty fortunate. Honestly, it was a good kick in the ass I needed to remind me that people everywhere, no matter what their circumstance, value the same things. They want to be part of a community, they want to experience beauty in their life, and they want to live in a place they can be proud of.


What finally hit me, is in knowing how much our surroundings shape us, then experiencing Florida conditions firsthand, how lucky we all are for the perseverance and dedication of every Floridian working to improve their place. We need you. We are counting on you.

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