My Entire Life Fit in a Ruby-Red Hatchback

Act V: Departure

I woke up on someone else’s sailboat.

Not my boat.

Not my future home.

One of the sailors from the club offered me his race boat for the night so I could make it to my next sailing class in the morning without driving an hour home, getting there around 11 p.m., falling asleep around midnight, and waking up early to drive right back.

It was practical. Mostly.

The boat was set up for racing, not living, which is a polite way of saying it was pretty bare. But there was enough room to sleep, and for one night, that was enough. It was my first night sleeping on a sailboat. It was quiet and surprisingly comfortable. I could hear the water running against the hull. A soothing sound that never gets old. It was also a little hot, because welcome to life on boats. Temperature control is not always part of the package.

Still, I woke up refreshed and excited for the day ahead.

I followed the instructions, shut off the battery, locked up, and then left quickly. The gas station was my only stop on the way to the marina. Apparently, breakfast was not part of the lesson plan.

Coffee was.

Priorities.

I thought this next sailing class would simply be the next step. More sailing, more practice, and more details. It was certainly that. The most important part of that class was not something in the curriculum. It was Captain Dave.

Captain Dave looked like an average middle-aged white guy from Jersey, accent included. A little loud, but we love it. He had the thing you want in a captain: calm, patient, and direct when he needed to be. Confident without making a show of it. He clearly knew what he was doing and he had the kind of leadership that makes you feel like things are handled.

At some point at the start of the class, he asked everyone what brought them there.

I told him about the dream. Live on a sailboat.

By then, I had said it out loud to coworkers, customers, friends, and probably anyone who stood still long enough, but this was different. This was someone inside the sailing world hearing it. The only others who really knew were the crew on Reverie, the boat I usually raced on.

I think he connected with it. He could also see that I was paying attention and taking it seriously. I didn’t know it then. That tiny moment mattered. At the end of the class, he mentioned another class coming up and handed me his business card. He said it might be a good fit for someone who wanted to live aboard. At the time, it probably sounded like a suggestion. Looking back, it was one of the next steps showing up.

The class cost more than the first one.

It was also in Florida, in April, on a catamaran.

I reviewed the evidence carefully.

Sign me up!

It was supposed to start and stay around St. Augustine.

It did not.

Bad weather had kept Captain Dave from getting the boat there in time, so instead of starting where we expected, we drove down to Titusville and brought the boat back north, which honestly made the whole thing so much better.

It stopped feeling like a class floating around in circles near a marina. It became a real trip. Point A to Point B: provisioning, weather, planning, bridge calls, engine checks, equipment checks, decisions, and taking turns playing the role of captain. We were not just learning how to sail anymore. We were living on the boat. Temporarily, yes, but still.

It was my first time on a catamaran. Compared to the race boats and monohulls I had been sailing, it felt enormous. Imagine steering a little condo on water. You had to be patient or you would overcorrect, which is rude because I had spent a good portion of my life overcorrecting emotionally and now apparently boats were calling me out too.

Fair.

I met John and Kym in St. Augustine before we headed to Titusville. They were other participants in this class. They felt comfortable almost immediately. Kind, easy to be around, and newer to this too, although John had some Hobie Cat sailing experience. There was something nice about not being the only one still figuring things out.

We were all stepping into something.

The trip became real for me the first time we contacted a bridge. There was something very cool about making that call on the VHF.

Someone had trusted me with a radio and nautical consequences.

Dubious judgment, but I felt extremely official.

That was different from sailing around a bay or racing around marks. Bridges meant timing, communication, charting. A boat with a destination. The class had become more than a class. We were moving from one place to another and living on the boat while we did it.

It was a taste of the life.

Not the polished version.

The real one.

More exciting. More beautiful. And more work.

All of it.

By the time we made it back to St. Augustine, I felt like another door had opened. We still had class work to do around the area, but something had shifted. The dream still did not feel easy or guaranteed.

It felt closer.

After the Florida class, I went back to normal life.

Mostly.

By then, normal life had a different shape. I was working full-time for Lyra Health, which meant I had to let Trader Joe’s go. That was a hard hit. I loved it there, but I didn’t have enough focus for everything.

So I kept my head in the game where I could.

I raced that summer. I stayed in touch with John and Kym here and there. Boat research was happening. I kept learning. What was the next step going to be? I trusted it would show itself.

Right on cue, Captain Dave invited me to join him for a delivery that December. The boat was going from Brunswick, Georgia, to Titusville. It had been brought out of Florida for hurricane season and insurance reasons, and now it was time to move it back.

There were two other people onboard with Captain Dave and me, a couple he knew. They were nice and much more experienced than I was, which meant I spent a lot of that trip watching, absorbing, and getting my hands in wherever I could.

That trip was also my first time in Brunswick, Georgia.

I knew no one there and felt out of place. I liked the vibe anyway. Michigan had gone gray, brown, and frozen. Brunswick had palm trees, blue water, and actual color.

Stat treatment for seasonal depression.

No prescription needed.

The docks were nice. Happy hour was great, even if I mostly kept to myself because everyone felt more experienced and settled than I was. Still, I saw the potential.

At one point, Captain Dave said something like, “This would be a good place for you once you have a boat.”

At the time, I didn’t know how much truth was hiding in that sentence.

Then Brunswick disappeared from my mind as we sailed away toward Florida.

I wasn’t thinking about where I would live yet. I was thinking about what kind of boat I would buy, what I could afford, and how I would manage the steep learning curve.

Captain Dave knew I had been a chef for twenty years.

Wouldn’t you know it, having a chef onboard for a boat delivery is a plus.

Plus plus plus.

We ate very well on that trip.

I was also learning in the galley. Cooking on a boat brought me back to familiar work with a different set of constraints. Smaller space. More movement. Different logistics. I started treating it like a professional puzzle.

How would this work?

How would I organize myself?

What would I do differently next time?

I even made fresh bread while we were out in the Atlantic, because why be normal when you can be extra and useful at the same time?

Also, personal bragging rights.

It was easier than I expected. Kneading dough with the motion of the ocean was not a problem. If anything, the boat helped. The BLTs we made with that bread were chef’s kiss.

We moored in St. Augustine just as the Christmas lights were being lit up. I had already loved St. Augustine the first time I visited, but arriving there by boat, in December, with the city glowing, felt surreal. The dream was no longer just something I talked about. I was moving toward it. The lights made the whole thing feel even more magical, like the world had decided to decorate the next step for me.

It felt like possibility had lights on it.

We got to Titusville the next day and stopped at the fuel dock. I remember seeing a boat right in front of us with two cats onboard and thinking, “I could totally have a cat on a boat.”

Important foreshadowing.

Then I went back to Michigan for Christmas.

It was bitter. Not “a little chilly after Florida” weather. Michigan in December, one notch below Quebec freezing. The contrast was hard to miss. A few weeks earlier, I had been in Florida, making bread on a boat in the Atlantic, arriving in St. Augustine under Christmas lights, feeling like the dream had started placing real steps in front of me.

Now I was back in winter.

Back in the life I had built.

Back in the life I was starting to understand might not be able to come with me.

That winter and spring, I kept trying things.

Indoor rock climbing, boat research, volunteering with a cat rescue. I wanted to give back somewhere, and I’m totally a cat dad. I was watching videos about training cats to climb, swim, and go on paddleboards, because apparently I was not just planning to live on a sailboat someday. Living on a sailboat with an adventure cat who had a better résumé than most humans? Hell yeah!

Then, in late April 2023, Captain Dave reached out again. His boat needed to move from St. Augustine back to Brunswick. John and Kym were coming too.

The reunion tour.

This trip felt different. Easier and more comfortable. Familiar waters, familiar people, and no class curriculum this time. We took our time, stopping in places like Fernandina and Cumberland Island. I had more confidence by then. We knew what we were doing.

Enough.

What I remember most is not the boat. I remember the connection. John and Kym had felt like my kind of people from the first day we met. This trip confirmed it. The conversations got deeper, and by the end, I knew they would be part of my life for a long time.

That trip helped me understand something about cruising and liveaboard life.

The boat matters.

Of course it does.

But the boat is only part of it.

A huge part of the life is the community you build along the way.

When we got back to Brunswick, it felt more familiar than the first time. I was still new. Still quiet. Still mostly keeping to myself. This was only my second visit. It was no longer a random marina in Georgia. It was becoming a place I recognized.

By then, the dream was no longer asking me to learn more. It was asking what I was willing to change.

Around that time, my wife and I started having conversations about separating and ending our marriage amicably. I am not going to unpack all of that here. Some parts of a story still deserve privacy. What I can say is that we were moving in different directions, and I was beginning to understand that the life I was moving toward would require choices I had been afraid to make.

They were the hardest conversations of my life.

I had already started purging what I owned. The sorting itself was not the hardest part. I Marie Kondo’d the crap out of it. Most things were easy. A few made me pause because they carried more history than their size suggested. I let them go anyway. Living on a boat would mean I could only keep what would fit aboard.

My measure was a ruby-red Ford Focus hatchback.

Very scientific.

If it did not fit in there, I wouldn’t own it anymore. At that point, though, I was still preparing for some undefined future.

Then Captain Dave reached out with another next step. His boat was in Brunswick. He asked if I would be interested in staying on it for a while. We had briefly touched on the idea in April, but this was the first time it became real.

I said yes.

Of course I did.

The offer turned preparation into departure. The loose plan was simple: stay on Captain Dave’s boat until I bought mine. Simple.

A rather generous word.

While I was there, I would look after the boat. Keep it clean, deal with whatever broke, and make sure any work that needed doing got done.

It was not my boat.

But caring for it would be my first real taste of responsibility for one.

It was a half step into the life.

And half steps count.

Now I had somewhere to go. I started calling what came next my intentional homelessness period.

Branding matters.

That was when the leaving became real. The hard part was not letting go of things. It was letting go of a life I knew. My wife. Our home. The life we had built.

The cats.

I said goodbye and almost ran away from the room.

That nearly broke me.

I knew it made more sense for them to stay where life was stable for them. I was heading into transition and uncertainty, and cats hate change even more than humans do. Knowing that did not make it hurt less. I grieved for weeks.

Before leaving, I went to Quebec to see friends and family while I still could. There was no way to know how easy it would be to return, or how long it might take. That visit brought me closer to some of my cousins than all the years before it had. It also gave me one more visit with my friend Louis in Quebec City. I didn’t know it would be the last time.

On July 14th, I packed my car to the gills.

Hi July. I see you again.

Everything I owned was in that car.

Everything else stayed behind.

I remember almost nothing about the drive. Not the music. Not the miles. There was no cinematic rearview mirror moment. My brain felt like a loud crowd where I couldn’t distinguish a single conversation.

What I remember is stopping in South Carolina for One Claw.

I had first discovered it in Asheville during the unplanned North Carolina trip that helped wake the dream back up. It is almost impossible to find outside the Carolinas, so when I found it at Publix, I had to stop.

It was pouring rain.

The parking lot was flooded.

I looked at the six inches of water between me and the store and thought, “You really like that beer, don’t you?”

Apparently, yes.

I waded across and came back with two six-packs.

Worth it.

Everything I owned was still packed into the car. My old life was behind me. My next life was unclear.

I was more scared than excited.

Just kept driving.

I didn’t have my boat yet and didn’t have the full plan. I had said yes to the next step, and it was waiting for me in Brunswick.

A 2007 Lagoon 440 named Serendipity.

Captain Dave’s boat.

Not mine.

Not home.

At least not yet.

When I stepped aboard with everything I owned still packed into the car behind me, it felt like the dream had opened the door and said:

“Start here.”