I’m not even going to wade into the bloodied debate over what counts as a yacht, a boat, a vessel, or a ship. Words fail to contain the truth of motion on water. Labels are for people afraid of salt in their veins. I live full-time on a 50-foot sailboat, a floating cathedral of teak and stubborn steel, an altar to wind and water and my own stubbornness. It isn’t the largest creature in most marinas, but it isn’t the smallest either, the way a wolf cub grows into a wolf without knowing it yet. It hovers in that cruel and perfect Goldilocks zone, neither too puny to be safe nor so vast that you drown in its own ego.
A 2000 Moody 46, she is my rhythm, my anchor, my chaos contained. Big enough to hold a family, small enough to be wrestled alone under an angry sky. Every line of her rigging, every curve of her hull is a conversation between desire and practicality, the way life itself negotiates with inevitability. The ocean speaks to her in waves that slap and sigh, and I listen like a desperate acolyte, learning her moods, anticipating her whispers. The deck hums underfoot, and the sails flex like lungs in a storm, breathing in a language that only the devoted can parse.
Couples sailing is an illusion of partnership. Really, it is single-handed sailing with a witness, somebody there to argue with you about everything: the course, the anchor, the absurdity of wind patterns, and the moral imperative of staying upright when the universe conspires to roll you. Every tack, every gybe, every night anchored in the whispering dark becomes a trial of patience, a negotiation with ego, a dance of shared stubbornness. And yet, in that chaos, there is intimacy, the kind that only comes from two humans clinging to sanity while the sea tries to shake it out of them.
You want to know how you live on a boat like this? It’s maddeningly simple. Stop buying stuff. Sell everything you own. Give it away, trash it, burn it, whatever it takes. Invest in skills and capabilities that aren’t tied to a place, a zip code, a mortgage. Take a chance. That’s it. Pretty easy to say, terrifying to do.
I was a senior government executive once, the kind who testified in front of Congress, led programs that mattered, or at least mattered to the people who think they matter. In my mind it was a little like James Bond. In reality, it was nothing like James Bond. Picture a cheap blue suit, a cheap car, drone-eyed and scurrying paycheck to paycheck. The trappings of a successful life stacked like Lego towers around me: huge house, lots of cars all needing work, every surface screaming responsibility. I was too old to jump off the treadmill, too tied to inertia to step away from the slow suicide of routine. Each day a slightly different flavor of drudgery.
Then the universe laughed. The job imploded, and I went from stud to dud in the eyes of everyone who mattered. Sitting in a conference room in Atlanta, I got a text from a prospective employer: work virtual, do your thing, have fun, help me be successful. And just like that, the horizon opened. My wife and I looked at each other and thought, okay, this is insane, but it might work. We sold, gave away, trashed, binned, broke, moved, destroyed, and divested everything from our 5000 square foot house in three months flat. Bought a boat and went remote.
We had been thinking about it for a while. Researched, visited, dreamed, but the act of divesting was what actually punched the world into reality. It’s a strange kind of shock: one month without stuff, without all the nonsense that eats your money, and suddenly the bank account bulges. Freedom tastes like a cold beer on a hot deck. Of course, that freedom evaporates the moment you buy a boat, because the ocean has its own rules, and the damn thing costs more than a small nation in monthly upkeep. But at least you’re moving, finally, away from the treadmill, away from the paper towers and fluorescent-lit prisons, into a life that demands attention, skill, and just a little bit of terror to keep it honest.
Some people plan early. The number of people who have followed the financial independence retire early way of breaking out of the rat race is legion. Boats are not cheap. Boats are far cheaper than real estate in the San Francisco Bay area, but cheap is relative. I have met people who saved and saved and saved until the cruising fund was fat enough to buy freedom. All of those paths work for people with discipline, patience, constitution. I am not that. I am a fat old man with a fondness for good bourbon and a distaste for waiting.
Here is the deal. I had to keep working. Working virtual was the only way to make this happen. I invested in the best routers, the fastest wi-fi hotspots, and created a life where I could work during the day on my boat, even sail while working, and be anywhere but trapped in a concrete canyon at night. Drinking bourbon. Whether anchored in the Bahamas, chasing the Gulf Stream across turquoise madness, dodging Boeing 747-sized mosquitoes in the Carolinas, or eating pancakes in a deserted Chesapeake anchorage. All the commute time, all the wasted hours that used to evaporate in offices and traffic, is mine. Results are the only metric. Am I getting results? If yes, the rest is just scenery.
You want to do this? You need a boat, the price of the boat again to refit the boat even if brand new, two to five percent of the boat’s value upfront for insurance, five to ten thousand for courses to learn how to operate it, and all the remote work accouterments: routers, hotspots, tablets, laptops, good computers. Couch surfing, crunchy commentariat will tell you go small, go now, and that is fine advice for them. I like good bourbon.
You want to do this? Watch YouTube, read the magazines, see the dream world of sails and sunsets and perfect mornings. YouTube and magazines are filtered, curated, sanitized reality. The actual life is hard work. If you are not up to that hard work, you will not last long. Over the last five years, I have watched people dive in and then bail. The average life of a cruiser is closer to mediocrity than adventure. Influencers with bikini deals and camera smiles drop out about a third of the time when they discover that a make-up channel or clothing haul makes far more money than fixing a rig in a rainstorm. Be my guest if you want that influencer path. I am the fat old guy in the anchorage, fixing leaks, patching sails, and drinking bourbon.
You also have to understand that many people running their job treadmills with white picket fences are hostile to this life. They do not want you anchoring in front of their homes on public land they do not own. Access to public land to come ashore is being tightened or circumvented in many places across the USA. Political and commercial influence is being used to make this lifestyle difficult, even illegal, if it conflicts with the interests of those with power.
COVID-19 may be mostly behind us, but the remote work revolution is far from over. I have found, and continue to find, that the job market has globalized. You can work from anywhere for anyone if you have a domestic address. Tax laws are complicated, but adaptable. FAANG companies may lay people off, but other companies are hiring. The confusion is part of the chaos.
You can do this if you plan, if you understand the risks, the rewards, the pitfalls. You need a mail service because mailboxes on boats are fantasy. You need a shore support network, whether family, friends, or paid consultants. Medical care is strange; outside the USA it is often incredible and cheaper than a good steak dinner.
You can do this if you are willing to step off the treadmill and claim the horizon as your office.
About the Author
