Living on a Boat: Lessons Learned from a Lifetime at Sea

Let’s start with a child. What does a child need? Love? Attention? Food? Water? Instruction? Protection? Education? Discipline? A sense of family, belonging, and group identification? The ability to work as a team? Tribal badging? 

Yes, exactly. And a small boat on a large sea is the perfect place to absorb these life-lessons, a perfect place to be nurtured—or die. 

Offshore, death is as simple as falling overboard. It must be guarded against 24/7. Life afloat has real-world consequences. If you can’t handle that, it’s best to stay ashore and cower with the rest. 

“Good boy!” my father would say as I steered the Elizabeth, our Alden schooner into port as he shaved, “a spoke to starboard, son. Good. Now another. Steady! Meet the waves—find their rhythm, move with them. That-a-boy! Now ease her back to port. You’re getting it—you’re a natural, son!”

My father taught me about the loneliness of command. My mother taught me the art of nurturing. My sisters taught me how to cooperate; and when not to.

My young nose was in everyone’s business. I learned how to bank our coal-fired Shipmate stove, how to simmer the fish chowder, and how to bake an apple pie. 

Father taught me how to fix things. He explained that fixing stuff was intelligence applied. And he brooked no excuse. If I didn’t have the right tool, he expected me to make one as a natural outgrowth of the fixing. 

My favourite time as a child was just after dark. Our family—all five of us—would lay on deck, stare up at the canopy of stars above, and sing. That’s right—we’d raise our voices in harmony. We’d call and respond. One of us would sing the verse, the rest would join in on the chorus. There was a certain rhythm—a pulse related to the heart. You had to take-stage to capture the vocal spotlight—you had to fade out so as not to hog it. 

Singing with my family wasn’t merely fun, it was educational. You had to cooperate by taking the lead sometimes and singing back-up other times.

Extreme 40s & the Future of Yacht Racing

Of course, there comes a time when a fledgling must leave the nest. At 15, I purchased my own $200 boat and from that moment on, my vessels have been the fulcrum of my existence. 

My childhood was all about learning how to not make mistakes. My teenage years were all about making other mistakes—and learning from them. 

I find it remarkable that my parents were able to ‘wave me over the horizon’ with more confidence than fear. 

Parents can be argued with—reefs and rocks, not so much. Kids need space to screw up, screw up, screw up—and thus learn how to succeed. Helicopter parents do a grave injustice. 

Once I had my life-partner in tow, I set about accomplishing my major goals. At nineteen, I began building a 36-foot, 20,000-pound offshore ketch from scratch. 

What better way to learn than to build a boat—and then sail it across oceans for a couple of decades? Was the boat that I built perfect? No. Close to perfect? No. Was she strong and did she function? Yes.  Could you measure me by her? You betcha!

And, yes, practice makes perfect. I’m a hedonist and a hard worker and I see no conflict between the two. My wife and I soon produced a daughter. As she crowned, I said aloud to my wife. “This child didn’t ask to be born aboard this ship, on this voyage—that is our choice, not hers. Thus, the sole responsibility for her safety around water is ours. We must keep salt out of her lungs at all costs.”

We did, diligently—just as my father and mother had done for myself and my sisters. 

Eternal vigilance is, indeed, the price of liberty, whether ashore or afloat. 

Next came our circumnavigations—our way of shaking hands with the citizens of the world. I soon realised that many of the best fathers in the world earned around two dollars a day, had dark skin, and didn’t take sh*t from anyone.

Of course, I had to earn my living. With only a total of five years of formal education and no salable tools—well, except for the cheap Bic pen in my hand.

Singapore Stan

“What cha doing Cap’n DaddyO?” our daughter would ask as she climbed in my lap. 

“Careful!” I’d tell her, “I’m wrestling a lion in Africa.” 

“Don’t be silly, Willy,” she’d giggle, “you’re reading a book!”

“Yes,” I’d say, allowing her a place in the crook of my arm to stare up at the pages, “Exactly!”

Then I’d read to her from my Wilbur Smith novel—translating the sentences into child-speak. And I’d do this within her teachable moment, not at my convenience. And the result was a child that loved to read—the key to the kingdom, in my humble opinion. 

The trick isn’t to keep your child away from drugs. That’s impossible in modern society. The trick is to give them useful tools to judge such drugs, not moralistic conclusions. Which drugs enhance life (like aspirin) or destroy it (like fentanyl)?

Then, toward the end of our fourth circ, the covid pandemic struck. Very few nations were allowing cruising yachts to enter. We sailed to Southeast Asia to be with our daughter, Little Miss Moneybags. She’s now making the big bucks at SMU, Singapore Management University. (Yes, we all rebel from our parents in different ways.)

We’re lucky—in part because we make our own luck. Once again, we’re in a delightful place in our life journey. We’re in each other’s arms as we watch the setting sun hiss into the ocean astern. Our grandkids cruise shorter-but-equally-fun distances with us. We teach them the joys of Mother Ocean. They, through their joyous smiles, keep us young. 

Why so blessed? In part, because I’m in my 64th year of living aboard. Our vessel is our magic carpet. All we have to do is wish. The entire world is on our cruising menu. We get to pick and choose, as the wind and whim strikes. 

No, I’ve never worked ashore, never labored for The Man. How? Why? Because The Man doesn’t have anything I want. His money owns him, not me. His dearest possessions are his heaviest anchors. Even the clod of earth he lives upon requires that he pays forever (taxes) and defends it (nationalism). Sad. 

I never aspired to be merely an American, or a white guy, or a Christian. I never even dreamt that being anti-science or anti-truth would become a thing. I never wanted to learn which end of the whip to grasp because whipping others offers me no joy. 

Is everything peaches and cream?

Yeah, pretty much.

We live aboard on a mooring—just provisioning by dinghy keeps us active and fit. Landscaped bike paths are everywhere. We ride every day. Parks are plentiful—each has an outdoor gym. 

Health care in Singapore is both world-class and nearly free by American standards. (A full day in the hospital, via the ER, with dozens of sophisticated state-of-the-art tests—and a handful of conferring doctors—recently cost me $150.)

We’re not at a yacht club, really—more of a communally-owned sailing club. Costs are modest; services plentiful. Example: to use the dock for a couple of days or get two power vessels to haul you off a sandbar or have four big guys help you remove/transport/replace your heavy batteries… all are done with a smile at no extra cost.

One of the few rules of the club is no tipping. 

In the world’s most expensive city we live like kings on a pauper’s (Social Security) budget. 

For all intents and purposes, there’s no (violent, physical or property) crime ashore or afloat. None. We almost never lock our boat, expensive bikes, or our newish dinghy/outboard in a city of six million. 

How safe are we talking about? When six of our granddaughter’s middle school girlfriends wanted to camp out for a weekend in the heart of the city—none of the parents raised an objection. 

…what was there to object about?

Public transportation is excellent and very affordable. Two years ago all the fares were reduced by four cents during their mandatory annual review—strange but true! (Just to get a permit to buy a car, however, costs $50,000! {Not the car, the right to purchase it!})

While it is easy to blow a grand on a gourmet meal at Wolfgang Puck’s in Marina Bay Sands—it is also easy to have a wonderful lunch for $3 at a clean, inspected food court—$5 if you’re a gourmet with a large appetite. 

But the best part, from our current 72-year old perspective, is how the Asians respect their elders. Everywhere we go, we’re treated with respect and deference. “How are you today, Uncle,” they ask me. “And is Aunty good too?”

Here’s the truth about Singapore—the Singaporeans are very competitive on all levels, especially about being considerate to each other and their guests. In the five years I’ve spent here during various circumnavigations, I’ve not only never observed any violence—I’ve almost never heard any shouting! Let’s put it this way—if you are utterly horrible to a Singaporean in public, they silently frown and it is you who lose face, not them. 

This is the only country in the world I know of that has no slums or bad neighborhoods—none! There’s no segregation or ghettos allowed here—no Muslim or Chinese or Malay or Indian residential neighborhoods—everything is computer-mixed by race and religion and wealth—so that diverse neighbors in the same building pay different fees to ‘level up’ the populace. 

If all that wasn’t enough, the Singapore passport is the most respected in the world. And when we (with our long term visitor passes) fly in or out, there’s no hassle—a machine glances at our retina and that’s it. 

There’s almost no police presence because there’s almost no crime—and part of the reason for that is that penalties are draconian: a 22-year-old Singaporean was executed last month for two pounds of ganja—yikes! 

And they cane the offender as well as throw them in jail. (Doctors supervise the canings—and halt/delay the process whenever the subject passes out from pain.)

Disgusting? Uncivilized? Perhaps. But there’s no crime. No graffiti. No vandalism. No theft. This means that everything in the city can be delicate and artistic and easily destroyed—because no one wants to destroy it. (Singapore’s local James Bond just brought a tourist back from Thailand (in chains) who’d stupidly defaced a MRT seat… a mistake the young man won’t make again, I assure you.)

Part of the reason I’ve circumnavigated so many times is to find such places—exotic destinations that offer a unique quality of life. Is there a better place to currently live than Singapore, a civilization more Garden-of-Eden-like? Perhaps. But I haven’t seen it—nor do I know anyone who has. 

And so every morning, noon, and night we eat in our cockpit in Serangoon Harbour—and marvel at our good fortune to be welcome guests in the most desirable nation/state on the planet. 

We’re grateful—especially to King Neptune, who punched our worldwide cruising ticket so many years ago.