When the Dream Started Asking for More

Act IV: Course Corrections

I was lying on the floor in the middle of my house, listening to the sound people always describe as a freight train.

It does sound like a freight train.

The tornado sirens were screaming. Branches were snapping. Rain was hammering the siding so loudly I could barely think. Somewhere in the house, my cats were hiding. I had no basement. The house was on a slab.

And I remember thinking, very calmly: “I might be about to die.”

Then, somehow: “I had a decent run.”

That was not the reaction I expected from myself.

For almost a year, I had been having panic attacks at night, terrified of dying for no obvious reason. Yet here I was, with an actual tornado passing nearby, and I was calm.

After it passed, I walked outside and saw branches everywhere. The trees had taken the hit. The house was mostly fine. I was fine. The cats eventually came out like nothing had happened, because apparently cats do not participate in existential turning points.

That same day, I booked my first sailing class. It took ten minutes. Two years of circling the dream. Ten minutes to act. It felt like the Universe was saying, “Good. You’re finally paying attention.” Clearly, subtlety had failed.

So how did I get there? How did a tornado become the thing that finally made me book the damn class?

This is the story of the two years I spent feeding the fire before I ever stepped onto a sailboat.

At the end of my trip to North Carolina, the dream of living on a sailboat had come back to life. So the obvious next step seemed simple enough. Get on a sailboat. There was only one small problem. I had never actually been on one.

Minor detail.

For over twenty years, I had carried the romanticized version of the dream. Freedom. Anchorages. Sunsets. Simplicity. Water. Beautiful.

Also completely untested.

I didn’t know if I would like the motion, the work, the cramped spaces, the weather, or the constant problem solving. I needed to find out. That seemed like a pretty important step. Life had other ideas.

That first year was not about sailing yet. It was about becoming harder to stop. I was working out. Eating better. Taking coaching seriously. I started my NASM personal training certification because apparently my idea of personal growth involved signing up for something notoriously hard. A flight to Dallas so I could learn about building a coaching business. I told my job I was leaving.

One by one, I kept adding logs to the fire.

None of it looked like buying a sailboat yet.

All of it mattered.

Sailing in Michigan was also seasonal, and fall was coming. Soon the boats would be coming out of the water. That was fine. I figured I would get to sailing in the spring.

You know, spring of 2020.

Great plan.

By December 2019, I was no longer working. I was officially starting my coaching business. That sounds so clean when I write it like that.

It was not clean.

I had freedom and, somehow, I had never felt busier. There was always a call to get on, a meeting I had set up, a conversation to have, a post to write, a thing to think about, a mindset to improve.

Lots of motion.

Not much movement.

I was trying to build something before I really understood what it was.

In January 2020, I finished my coaching course in Chicago. I also managed to celebrate hard enough to end the weekend with my first ambulance ride. Dehydration. Very glamorous. Not my smoothest exit, but I had finished.

A few months later, in early March, we went on a cruise to celebrate my 40th birthday and our 10th wedding anniversary. Aruba, Bonaire, and Curaçao. The ABCs.

I loved it there. The water. The islands. The feeling of being somewhere warm and alive and open. I went snorkeling often. The underwater world felt instinctively welcoming. I remember thinking how much I would love to sail there someday.

The cruise also happened to be an Abraham-Hicks cruise, which I did not know when we booked it. I’m not fully in that world, but I met wonderfully open and curious people. Someone even gave me their pass so I could attend some of the events. So for a few events, my name was Jasmine.

The cruise also showed me something I wasn’t ready to fully face yet. I was changing faster than my life could hold, and some of that change came out sideways. I wasn’t always as honest, present, or kind as I wish I had been. That’s still hard for me to sit with. It taught me something I carry into every relationship now: have the honest conversations sooner.

Then we got off the ship on March 15th, 2020. The shutdown started on March 16th. We had been mostly out of contact for ten days, so the world we came back to was not the world we had left. People were on their phones everywhere. Upset. Worried. Having strange conversations. We had messages from the person who had been watching our cats saying she had left toilet paper at our house.

At the time, that felt confusing.

Thanks, I guess?

Then we got to our hotel. It was empty. Not quiet.

Empty.

There was one person working the front desk and one person working the bar. When we checked in, the person at the front desk basically said, “Which room do you want? There’s no one else here.” That was when the eeriness really landed.

Wait.

What did we just come back to?

We started worrying about whether we would even be able to fly home. A few days earlier, I had been talking with dreamers on a cruise ship about possibility. Now the world was shutting down.

The coaching business had never really gotten off the ground. I had been relying heavily on in-person networking, and suddenly that disappeared.

I froze.

There’s no better word for it. I tried to adapt, kind of. The business was too new. I was too new. My mindset was not strong enough yet. I had left my job without a functioning business, and in hindsight, my wife was right to be upset about that.

Waiting longer may have made a huge difference financially. I also know I needed to leave that job to find myself. Both things can be true.

I started worrying about making mortgage payments. I drained my 401k to survive. That sentence still feels heavy. The dream was alive, but real life was very much happening. That was the strange part. From the outside, it probably looked like I had wandered away from the dream. Coaching. Money stress. Injury. Trader Joe’s. Paddleboards. Retreat ideas.

I hadn’t wandered away. I was learning how to keep going when the path didn’t look like a path.

And then, because the Universe felt the story needed a little physical comedy, I got the worst injury of my life in one of the stupidest ways possible. I’d like to say it happened while saving children and kittens from a burning house.

But no.

Sadly, this is a true story.

I was volunteering at a Chamber of Commerce golf tournament. I was stationed at a par 3. One foursome came through, and one guy was hesitating about which club to use. He hit his ball, got in the cart, and they drove away. They forgot one of his clubs at the tee box.

I figured I had time to bring it to them before the next foursome came through. I lazily jogged toward them carrying the club. Somehow, I twisted my ankle.

On a flat path.

You know how people say time slows down when you fall?

Not this time.

It accelerated.

One second I was jogging, the next I was on the ground, the club on one side of the path, my hat on the other, with absolutely no idea what had just happened.

What I did know was that I was hurt. Not “walk it off” hurt. Uh-oh hurt.

They never even saw me fall. I crawled back toward the tee box as the next foursome arrived. They looked at me and said something like, “You look really pale. Are you okay?” Apparently, my body had decided shock was the appropriate response. Only later did I understand why.

I called the organizer and my wife. I went to urgent care, where I complained about my ankle. Also, my arm kind of hurt. They focused on the ankle. Second-degree sprain. No breaks.

I went home, elevated my ankle, and watched TV. At some point, I put my hands behind my head, elbows out, trying to relax and ignore the pain. When I went to move my arms, only one of them worked. My right hand would not lift off my head.

“This is not good.”

The next day, I went to see my doctor. By then, a massive bruise had appeared on my tricep. She walked into the room, stopped, looked at me, and said, “Seriously… I can see it from here.” She could see the gap where the tendon should have been.

Oops. Turns out I had ripped my distal tricep tendon off my elbow.

That required surgery. Great… Just as I was about to look for a job. Of course. By the fall, I needed work. Any work.

I applied at Trader Joe’s after a few months. My arm was functional again. At first, it felt like failure. I had left a corporate cooking job to start a coaching business, and now I was going back to work in a grocery store with my tail tucked between my legs. It felt embarrassing. I didn’t just feel like the business had failed. I felt like I had failed. And now? A grocery store?

At least the people seemed nice. Then I started working there and I loved it. The place felt comfortable. Overall, my coworkers were great. I loved that everyone did everything, so you were not trapped doing one repetitive task all day. I enjoyed the movement, the autonomy, the simplicity, the social connection, and being heard when we had good ideas to bring up.

The customers were mostly great. Mostly. People were not always kind during COVID. Some were awful. Luckily, they were not the majority. They were just the ones you remembered most. Trader Joe’s became solid ground under my feet. Financial support. Social support. A place to feel useful. A place to belong for a while.

It also kept the dream alive in a way I did not expect. I would talk to coworkers and customers about what I was trying to do. Living on a sailboat. Coaching. Changing my life. Some people thought it was cool. Some probably thought, “Sure, buddy.” People would share their dreams too. I always encouraged that.

Every time I said it out loud, the dream felt a little more real. Even when I wasn’t moving quickly, I was still feeding the fire.

Sometimes with coaching, NASM, or even a grocery store job.

At some point during 2020, I had bought an inflatable paddleboard. I couldn’t get on a sailboat yet. So I got on the water any way I could. We had lake access, and during the week, around lunch, the lake was often quiet. I would launch from a small beach with a sandwich and something to drink, usually water or sparkling water. Then I would paddle out and anchor.

Literally anchor.

I had a small folding grapnel anchor tied to the paddleboard so I would not drift. I would sit there in the middle of the lake and eat my lunch. Sometimes I would lie down with something over my eyes and just listen. Small waves lapping against the board. Birds. Wind in the trees. The strange way sound carries over water, letting you hear distant conversations.

It was simple.

Quiet.

Present.

A man who dreamed of crossing oceans, anchored in the middle of a lake with a sandwich. Not quite the same thing, but it counted.

In early 2021, I was still trying things. A friend and I had been talking about putting together a coaching retreat, something with nature, mindset, emotional work, presence, and growth. I went to Gatlinburg to meet her and explore what that could look like. Since I was close enough, I also went back to the Blue Ridge Mountains in North Carolina.

I wanted to reconnect with that feeling from the first trip. That version of myself who had sat at the overlook and believed something else was possible. The retreat idea never really took off. A lot of things didn’t. But I was still learning what fit.

Dreams are not linear. Annoying, but true. You move forward. You wait, or you go around, figuring out another log for the fire.

After the North Carolina trip, the fire never went out. Sometimes it was small, other times it was roaring. It never came close to extinguishing. I kept paying attention.

Then, on July 24th, 2021, the tornado happened. The same tornado from the beginning of this story. Clearly, I just needed nature to get a little dramatic first.

That class was booked.

Two weeks later, I showed up for my make-or-break sailing class. I was nervous and excited. Afraid I might not like it and afraid I might love it. Both were dangerous in their own way. If I didn’t like it, what did that mean for this dream I had carried for over twenty years? If I did like it… Well, that might be worse. No pressure.

It was a cloudy day. Not too hot. Comfortable. I got there early because of course I did. The marina felt good immediately. I walked the docks for a while and looked at different boats. I didn’t know much yet. Completely unfamiliar with brands, layouts, rigs, or what made one boat different from another. I just knew they were sailboats.

The class boat was a Catalina 30. At the time, it was simply the boat for the class. When the captain and the other students arrived, everyone started getting aboard. I stepped on last. That moment is etched in my brain.

I felt my weight make the boat rock a little bit. I loved that feeling. And I remember thinking: “This just cost me soooo much money…”

Because I knew immediately.

Oh no.

The dream was on.

I knew at that moment I would buy a sailboat. I didn’t know when, or how. But I knew.

Moving around on the boat felt natural. I felt at ease. Then we got the sails up and turned off the engine. That is the moment sailors live for.

The switch between noise and silence. Engine to nature.

The wind gives you something. You try not to screw it up too badly and when you get it right, the boat moves like it was waiting for you to understand. It’s always willing to remind you who is actually in charge.

Sailing came to me pretty naturally. The names of things took longer, because everything on a boat has a name, and half the names sound like someone made them up after too much rum. But the feel of it made sense. The rest of the weekend simply confirmed what I had known the moment my foot touched that boat.

Yes. I liked sailing. A lot.

At the end of the class, we were basically told, “Now you can go practice.” Great. Tiny issue. I still didn’t have a sailboat. So I needed the next step.

Again.

The captain told me about a sailing club nearby. They were always looking for crew. They had weekday races and some Saturday sails. Perfect. Driving home, I was reliving the whole weekend and already thinking about how to arrange my schedule so I could sail regularly. I may have looked up the sailing club on my phone at red lights. Not something I recommend. Also, who reading this has never done that?

That evening, I reached out to some members through Facebook, hoping someone would reply. Someone did, and he invited me to join them for a race. When I showed up, he welcomed me and made me feel like I was part of the group. He taught me a lot, even in that first race.

Later, I met a couple I got along with very well. They took me under their wing. Reverie became my regular boat. A very fitting name for what I was going through. They were great teachers and patient with me.

I didn’t love racing because I cared about winning. I loved racing because it taught me quickly. Understanding was the goal. Racing taught me that tiny adjustments make big differences. It taught me to read the wind by looking at the water. Shiny water meant no wind. Widespread whitecaps meant you were already above about fifteen knots. You could see gusts before you felt them.

I learned steering, boat feel, and sail trim. I made mistakes. Every boat is slightly different. I sailed on boats from twenty-two feet to forty-five feet and got to see how much living space changed below. I got to feel different hulls, different rigs, different personalities.

Another perk was sailing in heavier wind than I would have chosen on my own. The race cutoff was forty knots. Below that? We were racing. That experience mattered.

At first, even leaving the slip made me slightly nauseous. Not throwing up seasick. Just uncomfortable. Then once we were racing, it would calm down and I would be fine. Eventually, I noticed it stopped.

My body had been learning too.

Those Tuesday races were tiring. I would get up at 4 a.m., work all day, drive an hour to the club, race, then drive an hour home to finally get back around 11 p.m.

Tired, yes.

But I was already looking forward to the next time.

Around that same season, Lyra Health entered the picture. In September 2021, I started doing paid coaching work again. It was part-time contract work at first, and I kept working part-time at Trader Joe’s. It felt good. I had been coaching during that time, mostly volunteer coaching, but this was different. It was consistent and was paid. It was moving forward. That mattered.

By the end of that summer, my life was not magically fixed. I still did not own a sailboat. How would this dream would become a life? I was still climbing. But something had changed. I was coaching again, and sailing every week. I was learning.

The dream was alive now.

It had weight.

It rocked under my feet.

And somewhere along the way, it had taken on a life of its own.

The next steps started showing up.

Not all at once.

Never that convenient.

But enough for me to recognize them.

And say yes.