I was 22 years old and 30 days out of college. Set to start law school in eight weeks, I was pursuing my dreams of service, justice, and eventually, judicial robes. But at that moment, those dreams were giving way to another career I was imagining: lawn guy. Mowing lawns, trimming hedges, planting flowers, and tending shrubs. Hooking up irrigators and hauling off palm fronds. Pruning, clipping, raking.

I was vacationing in Naples, Florida, where I envisioned a life in lawn care.

There were four of us in Naples that July in 1980, staying in my grandmother Honeywood’s cottage, close to the beach, close to the iconic pier. College friends, we were celebrating our page-turning moment, leaving undergrad and stepping into adulthood. John was going to the sales department of a major corporation, Ben was set to be a national rep for our fraternity, and Mac had a desk at his family business. I had a seat waiting for me at the University of Kentucky Law School … and I didn’t want to go.

I did go, but I didn’t stay. I lasted all of one semester. Even though my grades were OK, I wasn’t. Looking back, I’ve long thought I was simply tired of school. After blazing through 16 years of grade school, middle school, high school, and college, I needed a break. A gap year, I guess. And it didn’t have to be a year of backpacking across Europe or digging village wells in Africa. It could have been a year of mowing Bermuda grass in Naples.

And maybe it would have been more than a year. In lieu of paying rent to Honeywood, I could have stayed there free in return for taking care of the cottage and yard. Or I could have fixed up the little guest house and lived there. But I did none of that. Instead, I enrolled—and soon disenrolled—from law school.

I’ve been to Naples many times since that final trip with my college buddies, and it’s not the same town. The area’s population has swelled from 6,000 in 1980 to around 472,000 today. I have to think that any lawn care company I opened in 1980—with a mower, a trimmer, and an assortment of clippers, ladders, loppers, and shovels in the back of a pickup—could have grown with the town. With more people and more lawns, I would have added more mowers and loppers—and employees—and amassed a fleet of pickups and trailers.

I would be the overlord of lawn care in Naples.

And if not lawn care, then some other line of work. Lots of businesses a young guy launched in 1980 Naples could have grown into an empire over the last four decades, as the quiet beach town boomed into a sun-drenched paradise for the wealthy. Start small and grow with the population. I could have painted parking lot lines or detailed golf carts or delivered live bait all over town. I could have managed the rental of Honeywood’s cottage while I lived in the guest house—or the other way around. Then I might have helped a neighbor prep his house for rent … I might have bought it myself and flipped it. And then flipped another house.

I could have made a fortune as a young man in Old Naples.  

During my most recent visit—now an old man—I saw one more business I could have started in little-bitty Naples back in 1980: Bob’s Barricades. That name was on the back of an orange SLOW sign on Highway 41. Think of it: When I was 22, I could have bought a few road-construction signs and built some sawhorses, and then rented them out for one project after another. With the profits, I could buy more signs and sawhorses … maybe some smudge pots, those flaming cannon balls of road work.

Over the years, Naples added roads as fast as it added snowbirds. If my company had grown with Naples, I’d be the duke of DETOUR, the magnate of MERGE LEFT, the ruler of ROAD CLOSED. I would have been the Bob of Bob’s Barricades.

So what stopped me? What kept me, back in the summer of 1980, from letting my friends go north to their jobs while I stayed in Naples? What held me back? What was Bob’s barricade?

Oh sure, ditching law school in favor of lawn care would have raised a few eyebrows, but it wasn’t an insane idea. I could have explained to my family and friends that I was taking a non-backpack gap year, a detour, if you will, on the road to a legal career. And then I’d see how it went. I would not have lacked for company, as my Kentucky friends—and Honeywood—would have certainly visited, and I would have made new friends right there in Naples.

I could have made that bold move. I had a place to stay, a willingness to work, and an almost-developed plan. What I lacked, I guess, was guts. I feared I would take a bold step and fall flat on my face. The idea of returning home with an empty bank account and a back seat full of SLOW signs must have seemed too great of a risk.

I was afraid I’d fail.

Now, don’t get me wrong. I’ve had a wonderful life in Kentucky, marrying a fantastic woman and helping her raise two tremendous sons. I worked several jobs before settling into association management, writing magazine articles and marketing pieces for a packaged travel association. I live just outside my hometown of Midway and could not be happier.

But there is one thing—one unscratched itch. I have a novel inside me that’s been trying to get out for decades. I’ve mapped the plot, created the characters, and collected detailed information to capture the story’s 1980 setting … in Naples. It’ll be a great book, but I can’t seem to write it.

I’ve written plenty of other things and even published books of my own. I turned an annual tradition of writing Midway-based Christmas stories into a collection of short stories. I recently published a series of essays on my family’s connection to a particular house in Midway, now a famous restaurant. I even published a collection of poems I wrote during the emotionally jagged days of 2020.

But I can’t seem to write that novel. I’ve read up on writing techniques to help me tell the very best story. I’ve tweaked the plot and fine-tuned the characters, I’ve started Chapter 1 several times … and stopped every time. One minute I’m confident I can plow through the whole first draft in a month or two, and the next moment I put on the brakes, thinking I don’t yet have it exactly right. Bob’s barricade in writing a novel is pretty much the same thing that stopped me from taking a risk and remaining in South Florida forty-four years ago: fear of failure.

It’s an enhanced fear, though. See, I believe the story I’ve envisioned is possibly the best idea I’ll ever have. And if I blow it—if I write a novel that doesn’t match its potential—then I’m screwed. I will have frittered away my best idea—blown my big chance. I will have wasted my shot at writing the Great American Novel … that gets translated into thirty-five languages … and made into a movie.

That’s what halts me in my tracks: fear of epic failure.

When I was in Naples last month, I found a new barricade—a literal one. An important setting in my story, the Naples pier was wrecked by Hurricane Ian, and I couldn’t even walk out on the planked promenade like I’ve done a thousand times. Today’s stub of a pier no longer matches the murder scene of my ’80s-set story.

So I’m still tapping the breaks on my novel, and I can’t get over the hump. Maybe that’s a normal thing; I don’t know. Maybe everybody has one barricade or another, blocking them from stretching higher … from reaching a goal. Do you?

My novel isn’t ready for the junk pile. In the same way they’ll build the pier back, I can reassemble my cast of characters and reconstruct the tale they get caught up in. The pier, the people, and the Naples of my past remain very much alive in my mind. I’ve still got all the notes I took from my research on how to strengthen plot, characters, and dialogue. Plus, I’ve been thinking that instead of writing in third person, I could introduce another character who could narrate the story.

I missed my chance to hit it big as the lawn care king of Naples; hundreds of guys filled the void I didn’t dare enter. But I can still write. And there’s a laptop sitting right in front of me, waiting for me to type word after word of my story. I can still get it done. Hey, I’m only 65 years old—just 15,925 days out of college.