We Probably Bought the Wrong Boat — And Kept Sailing
Regret arrives. We keep sailing anyway.
“We should’ve bought a different boat.”
We’ve each uttered these words countless times over the past 19 months — especially early on.
Chérie had too many problems. Too slow. Too manual. Too cramped. Not great upwind. Things still broken.
“We could be doing this whole thing differently,” I’ve thought. “And better.”
But after we bought our little blue sloop, her flaws were ours.
She’s a small, South African-built, tough-as-nails Morgan 31. Her systems & tech were mostly end of life after a family of 3 lived aboard for 10 years & crossed multiple oceans. Lots of potential, but an enormous project.
When we bought Chérie, we had reservations. But with little knowledge or experience, we did what we thought was right. Then we dealt with the consequences.
Months of blood, sweat, & tears in a hot North Carolina boatyard.
Rotted fiberglass around the mast.
The engine totally kaput & needed to be replaced.
Broken, outdated, or missing parts meant tons more money & work.
We invested nearly 1 year & 2 more Chéries getting something we thought we already had: a nearly-ready boat.
She’s never been perfect.
When she was finally “capable,” I quit my job & we left the docks.
Then we put her to work. Nearly 4,000 miles. 11 states up & down the U.S. East Coast. Now through countless islands in the Bahamas.
And still, I imagine the paths that didn’t happen.
A bigger boat that cuts through waves like butter.
A warmer boat that could’ve taken us to Maine & Nova Scotia.
A newer boat that could’ve confidently completed the 1,500 mile sail from North Carolina to the Eastern Caribbean.
Those lives exist in my head.
Yet every night, lying in my berth at anchor — with the wind in the rigging & water sloshing against Chérie’s bow — I remember:
There’s no use ruminating too long.
I love my choices, imperfect as they are.
I can’t give the counterfactual that much power.
Regret arrives. We keep sailing anyway.
The Boat We Bought
Back in summer 2024, we walked through that North Carolina boatyard full of excitement. We were still learning about sailboats. We thought we knew enough. Then we made our first huge mistake:
We fell in love.
Chérie sat proudly on her stilts. We were mesmerized by her story & potential.
“She’s sailed to New Zealand! She’s been in the Amazon River!”
We thought we were getting a steal.
But we didn’t really know her.
Then we tore her apart.
And that’s when we learned the extent of her problems.
I could waste hours stewing about an alternate world where we bought the perfect sailboat at the start. But that would be beyond useless.
In retrospect, sure, I occasionally wish we’d chosen differently.
And beyond the sailboat, I think about all that we could’ve done differently:
A different sail plan.
A different anchorage.
A better dinghy.
A wetsuit for the Bahamas (actually, that might’ve been my biggest mistake).
But there was no timeline where we could’ve known all the undiscovered quirks, undeveloped preferences, & unknown unknowns.
We excluded those other timelines at every turn.
But importantly:
We didn’t need to ask permission.
We decided what mattered most & moved accordingly.
We respond to life as it actually unfolds.
We’re building a life with no the fewest regrets.
That’s the freedom we crave most.
Boats Are Compromises
I’ve never heard of anyone make a perfect choice in matters as complex as buying a boat.
Yes, we made verifiable mistakes.
But boats are compromises.
We always have imperfect knowledge.
Same with a life.
People regret careers. Relationships. Cities. Degrees. Investments. Mentors.
I think about the bad blood between me & my old PhD advisor. I know people who are best friends with theirs & I wish mine had turned out differently.
I could go on & on.
But regret is useless for more than 2 minutes.
There was no version of me back then with more wisdom than the one who chose & then chose what to do next.
You act before you feel ready.
If you wait for perfect, you might never get a boat let alone leave the damn dock.
“Marry, and you will regret it; don’t marry, you will also regret it; marry or don’t marry, you will regret it either way.”
—Kierkegaard
Perfect winds only exist for brief moments.
Perfect confidence only materializes after you’ve messed up 10 times.
Perfect information doesn’t exist ever.
These days, thankfully, I’m less interested in what my boats looks like & more interested in where she can take us.
We push forward knowing we might later wish it went differently.
We don’t dwell.
We sail.
Regret Means You Chose
We didn’t really know what we were doing when we started our sailing life.
Experienced sailors will tell you we did everything wrong.
I’m almost embarrassed to admit all this.
We bought Chérie on stilts. No sea trial.
We only saw a few boats. Few comparisons.
We knew the engine might not work. We signed anyway.
But I’m writing this 19 months & 4,000 miles later from the Bahamas, so I feel less shy about sharing all these facts.
Still, I would never argue that we did this perfectly.
If you, dear reader, were buying a boat, I might even try to instill all our hard-earned lessons.
You should sail on other boats first & learn what you like.
You should spend more money & save some pain fixing everything yourself.
You should buy a boat with a known reputation & someday it’ll help with the resale value.
But I also wouldn’t judge you if you ignore everything I just told you.
The important thing is you made a choice.
Then it had to work.
I’ve wrestled with the imaginary universe where we had “the better boat.”
Of course that fiction wins in my head.
But any brief regret still only means one thing: We made a damn choice.
We bought a sailboat.
We left the docks.
We learned to sail.
We left the U.S.
We sailed through the Bahamas.
We’re heading to a completely new world in weeks.
The ghost boat never existed.
The real one crossed the Gulf Stream.
The real one carried us nearly 4,000 miles.
The real one is our home.
It Has to Work
I already mentioned I’m writing this from the Bahamas.
Today we’re heading east to Long Island – our first time leaving the Exuma island chain in over a month.
The winds aren’t ideal (they rarely are). But this was our window. And so we’ll keep sailing.
In Long Island, we may spend about a week exploring. We’ll even splurge for a rental car & visit the world’s 3rd deepest blue hole. Then, we’ll head south & explore some more islands.
Later this month, we’ll be prepared for our longest sail yet:
800 miles from the Bahamas, between Cuba & Haiti, past Jamaica, to Guatemala. 10 days. More or less.
Chérie may not be perfect. But she’s mighty capable.
Will we eventually regret aspects of our next choices?
Almost certainly.
But once you choose, it has to work.
“Accept whatever comes to you woven in the pattern of your destiny.”
—Marcus Aurelius
Just Enough
Chérie has about 100 square feet of living space — basically a small parking spot that floats.
No working fridge
Blocky cockpit with stained & chipped fiberglass
Unfinished wood interior with so much potential
And:
A home that can cross oceans
Sunsets & stars every night
Freedom built into the day
Not bad huh?
Plus:
2 self-steering systems (a windvane & autopilot)
2 huge propane tanks
A gimbaled stove
Handmade cushions (by yours truly)
Massive freshwater & diesel tankage
New sails
Full keel
New engine (honestly we’re so grateful now)
We anchor in the same harbors as the $10 million yachts.
We get the same sunsets & stars.
Yes, there are aspects of Chérie we still wish were slightly different.
But now I focus on which metrics truly matter.
She’s enough.
Any other sailboat would’ve given us a different life.
And even a suboptimal sailboat can carry an optimal life.
Is This The Life You Want?
Nietzsche proposed asking whether you would live this exact life again — infinitely.
All of it. The mistakes, the doubt, the seemingly endless repairs.
According to him, this is how you test whether you’re living The Good Life.
So:
Would I choose this exact configuration again?
Maybe not exactly. There are too many possible good lives.
But this one – on the water instead of an office?
Yes. One million times.
I’m aware of 1,000 other adventures I’ll never live. There’s a momentary sadness in that fact. Then it passes.
I can’t stew.
This is what’s happened. And I love what’s happened.
The sunsets. The stars. All the winds. The 800 miles ahead.
Some nights in my berth, I think: would I be happier on one of those other adventures?
But then I look around. I’m on a sailboat at anchor in a new country. I’m living my radical path.
I can’t become bitter.
That would be insane.
Even with the flaws.
Even with the uncertainties.
Even with the compromises.
I’d live this life again.
Infinitely.
I’m sharing all of this in real time.
If you’d like to follow the full journey (& help keep it going), you can upgrade for $5/month or $50/year.
You can also chip in for a one-time donation, if that’s more your hull speed.
Until next time,
—Cory
Thanks Cory, having bought a rival 32 and spending the last year or so bring her up to scratch I look forward to the next part of my journey and the second part of yours greetings from Plymouth UK
Great article, Cory! Reminds me of a Dear Sugar advice column (written by Cheryl Strayed) called "The Ghost Ship that Didn't Carry Us". There are countless other lives out there on the horizon that we did not choose. We make the choices we make and grieve the ones we didn't and then we LIVE!!! We live because this is the one shot we get and, yes, hindsight is 20/20, but we can't go backwards!