When “Next Year” Stopped Feeling Guaranteed

One Week Before Leaving for the Florida Keys

My boat looked like a marine supply store had exploded inside it. Tools covered every available surface. Parts were scattered throughout the cabin. Ongoing projects seemed to occupy every square foot of living space. Battery system component boxes sat on the stove. Half-finished cables snaked across the cabin sole waiting to be connected. At times I had to step over projects just to move around the boat.

“What the hell am I doing!?”

You forget how many little things you actually need. I had so many thoughts of “oh yeah I’ll have to make sure to get that too…”. I was beginning to suspect the boat project list was possessed, writing itself specifically to create more chaos.

Standing in the middle of the boat staring at the mess, I was wondering whether leaving in seven days was ambitious or completely wild. The answer was probably yes.

The funny thing is, this trip wasn’t supposed to happen yet. It was a next year plan. Next year I’d have more experience. Next year the boat would be ready and I’d know what I was doing. Or at least be able to convincingly pretend.

Then a childhood friend passed away. He was almost exactly my age. He had spent his life getting ready. Studying to get good grades, to get a good paying job. Saving money to buy a house and having plenty of money for retirement. He got the house and never made it to retirement. Suddenly, next year stopped feeling like a guarantee.

At his funeral, I remember telling his sisters something that surprised even me. As sad as this was, it made me want to live more. I had felt that before. The words came out before I had really thought about them. But they were true.

The difference this time was that I was actually going to do something about it.

And now, standing in the middle of a disaster of a boat seven days before departure, those words felt a lot more real. I wasn’t just trying to get ready for a trip anymore. I was trying to follow through on a promise.

What I did have was a sailboat that I loved, a cat trying his best to help, and a growing inability to ignore the pull of seeing new places. I was tired of waiting until I felt ready. So I moved the timeline up drastically. I decided in mid-June that I would be leaving mid-November. Five months to get as ready as I could.

Not because I felt confident. Because I didn’t. Oh my God did I not feel up to the task. Every day seemed to bring something new to figure out. Boat ownership has a special talent for reminding you how much you don’t know. I’d solve one problem and immediately discover another hiding behind it.

Most of the time it felt overwhelming. At other times it felt exciting, sprinkled with moments of feeling truly alive. Then there’s the “I have made fire!” moments. The ones where you stand back, look at something you just accomplished, and think:

“Holy shit. I actually did it!”

Those moments are intoxicating. Not because of what you accomplished, but because of what it proves. A problem that felt impossible yesterday is now solved. Something that once intimidated you no longer does. Every one of those moments becomes a piece of evidence. Evidence that you can learn, adapt, and that you can figure things out.

For the first time in a long time, I wasn’t just thinking about the life I wanted. I was actively building it. Imperfectly. Messily. One uncomfortable step at a time. I had no idea what would happen once I untied the lines. What challenges were waiting for me? I didn’t know what I was about to learn, I just knew I couldn’t ignore the pull anymore.

Prioritization actually needed to happen. What was a “good to have”, and what was “absolutely not”. I redid my battery system to have more power and better charging. A must when living away from the dock.

Seven days later, if everything went according to plan, I’d point the bow south and leave Georgia behind. The boat wasn’t ready. I wasn’t ready. You never are. Yet it would be time to go.

P.S. Setzer contributed heavily to the preparations. His responsibilities included napping, demanding cuddles, and positioning himself in exactly the spot I needed to work. In fairness, when you’re standing in the middle of boat projects asking yourself, “What the fuck am I doing?”, emotional support is an important job.

Author’s Note: This story takes place in November 2025, one week before I left Georgia for the Florida Keys. It was originally shared as a short social media post and has been expanded here with the benefit of hindsight.