How I Bought the Wrong Boat (And What It Taught Me About Starting The Journey)
- Isaac Lester
- 4 days ago
- 11 min read
Still working out the particulars on how I want to actually connect everything, so for now you can read the article here, or listen to it over on Lester's Letters. Enjoy
It's been 48 hours since I flew across the country with a few thousand dollars scraped together from savings, emergency sales, and extremely lucky circumstances. Forty-eight hours since a stranger prayed for me over the phone and I decided this was my way out of my mother's basement in Chicago.
I've successfully arrived in beautiful Dana Point, California. It's been two days of peace. I'm standing in La Sirena's cockpit, and the engine won't start.
The marina wants the boat gone by Friday.
I know less about sailboats than I know about quantum physics.
And I just spent nearly everything I had.
I bought the wrong boat with money I didn't have, and it was the best decision I ever made.
I. Gambling With Mr. Craigs List
Let's go back.
August 2024. I'm in my basement dwelling in my mother's apartment in Chicago. I've been attempting to help in a deteriorating situation for the past two years while working to fix my own life as well.
It has not been easy, and after this last argument, I'm ready to just leave it all behind.
I opened Craigslist and looked for sailboats in California. Shotgun replies to every boat that looked attractive was the name of the game.
La Sirena appeared. 28 feet. $4,000. Pictures looked clean enough. I sent a message expecting nothing.
We were on the phone a few hours later.
I didn't mean to, but he asked how I found the listing, and my entire situation just poured out. Everything. The basement. The betrayals. The desperate need to escape before I became the broken thing I was surrounded by.
He listened. Then he prayed for me over the phone.
I was on a plane the next day.
Here's what I tell people now: I didn't want to risk everything on one bet, but staying in Chicago was guaranteed failure. Moving to California was only probable failure. It's not the first time I've done the math honestly and discovered that the "reckless" choice had sneakily became the most calculated one.
So do your math.
II. My 48-Hour Love Affair
The owner actually picked me up from my hotel and took me to the marina. La Sirena sat in her slip, white hull catching the California sun, and for the first time in years, I felt something other than trapped.
He showed me around and of course there were minor things here and there. Some cosmetic damage proved that children had enjoyed long summers days on the float in the past. The minor repairs that I could spot told me that she'd had her time on the water, not just racking up loitering points in her slip. I thought "nothing I can't figure out."
The important part: he turned the key, and the engine fired right up. No problems.
I sent him $4,000 in digital cash. Crazy world we live in.
For twoish days, I lived on that boat and discovered peace I didn't know existed.
The gentle rock of the water. The sounds of rigging clinking against masts in the evening. The sunset through the portholes. The simple act of making my favorite sandwich in a tiny galley while floating.
I'd been living in fight-or-flight mode for so gorydamn long that I'd totally forgotten what stillness felt like.
I fell in love with the lifestyle immediately and committed to diving deeper. I spent hours watching YouTube videos about sailing, reading forum posts, learning terminology. I had no idea what I was doing, but I knew this was right and needed more.
"Sometimes you're not buying the thing you think you're buying."
I'd heard this saying before, but this experience helped me understand multiple sides of it personally.
I thought I was buying a sailboat. I was actually buying an education.
III. The Guttiest of Punches
Day three. I get curious and cautiously insert and turn the key.
Click. Click. Nothing.
I try again. The engine that started perfectly for the previous owner two days ago now refuses to cooperate.
I call him. There's a pause on the line that lasts too long.
"Oh yeah," he says. "It's always been a bit temperamental. Usually fires right up for me after I prayed and fumbled long enough to attract the attention of someone to come help me."
My stomach drops into my balls and my bowels feel suddenly full. There's sweat already breaking through the top layer and seeing that California sun for the first time.
I look around for someone to ask for help, and find a tired but kind looking fisherman to come take a look.
"Yeah, she's seized up, and sounds like you're gonna need to replace something inside there"
My head feels light, and I can hear my heart beating. Terrible thing, to become viscerally aware of your own blood racing through your body.
I start looking closer at things I missed. Mold in the head I didn't see during the walkthrough. Damage in the photos that looked cosmetic but goes deeper. The marina manager informs me casually that La Sirena needs to be moved by Friday. Slip rental racked up to 4k. Even though it's paid now, and they want her gone.
Imagine that.
It's barely Wednesday. Fuck.
When crisis happens to me now, there's a critical moment where emotion floods in like the Great Wave. Panic, anger, feelings of betrayal, etc. It takes a pause, but storms always pass. What follows is a form of intentional calculated coldness toward the situation and the tasks required to resolve it. It's not healthy, probably, but it's how I survive.
I assess my options with Marine Corps logic: "Act like you have shit to get done."
Option A: Learn engine maintenance in 24 hours. Diagnose the problem. Order parts. Find someone who can install them. Locate a new marina willing to take me. Somehow move a sailboat I don't know how to sail to that marina using an engine that still might not work.
With what money? With what knowledge? With what time?
Option B: Accept the loss. Donate La Sirena to charity. Use the last of my cash to fly to Chicago for winter clothes, then take an Amtrak to North Carolina where a friend from my deployment days lives on his own sailboat. Crash there. Start over from a stable ("stable") platform.
I could fight to hold onto temporary peace that would collapse into chaos, or I could sacrifice the moment for long-term stability.
I chose stability. I will always choose stability.
There are times where we must work to look past the things we want in order to secure the things that we need. I ate the loss because I was honest with myself about what I could and couldn't accomplish with the resources I had.
IV. The Donation
The weekend drew near, and I didn't want to wait around. In my mind, I had an Operation to throw down on. Thursday.
For La Sirena, I felt grief and relief in equal measure. Grief for the dream I'd held for a handful of days. Relief that I wasn't going to destroy myself trying to save something I wasn't equipped to save.
I flew to Chicago. Packed winter clothes. Bought an Amtrak ticket to Raleigh with the last of my money.
On that train, something shifted.
My next boat hunt would be different. I wasn't operating from desperation anymore. I didn't have much, but I did have some experience now. More than I'd had a week ago.
La Sirena taught me what to look for in a boat. She showed me the questions complete novices need to ask. She revealed the gaps in my knowledge that research alone couldn't expose.
She taught me that "you don't know what you don't know" is a fundamental law of starting anything new.
I spent the next few months in North Carolina walking boatyards, talking to liveaboards, learning from people who'd already made the mistakes I was trying to avoid. I made finding my next boat part of my identity: "I will find a
sailboat to acquire and inhabit, and I'll work from there to build back everything I lost."
"I Will."
When Facebook Marketplace brought me Matilda in January 2025, ironically also for $4,000, I was a different buyer. I knew what to inspect. I knew what questions to ask. I knew the difference between "needs work" and "will bankrupt you."
Her engine ran, and runs (knocks on wood 5x).
I moved aboard a month later.
Matilda is teaching me what La Sirena never could: how to actually live on a boat. How to embrace the peace and stillness. How to build a life on water.
I'm grateful for both experiences.
V. Patterns You May Recognize
Right now, you have a La Sirena in your life.
Maybe it's:
- The business idea you've been researching for six months
- The course you've been planning but haven't launched
- The conversation you know you need to have
- The move you know you need to make
- The relationship you're trying to save that's already sunk
You're in the research phase. Analyzing. Optimizing. Waiting for the perfect moment when you have enough money, enough knowledge, enough certainty already.
Let me save you time: The perfect boat doesn't exist!
Here's what I learned from buying the wrong one:
Starting wrong teaches you how to get right. Staying paralyzed teaches you nothing.
Even here, what would you be doing if you were unable to read this article because I never started with the first version of this website? Would your opinion on starting wrong change if I told you that this is the 4th iteration of well past the 20th version of TheIsaacLester.com? I thought each design was "perfect" at the time, and each design has been edited, revised, and changed. 80% is good enough, yo'. it's gonna evolve over time anyway.
You're worried about making a mistake. I'm telling you the mistake is the education.
Think about it:
- I stayed in Chicago = Right choice (family, stability, logic), completely paralyzed
- I bought La Sirena = Wrong boat, but ... moving!
- I donated La Sirena = Wrong situation, honest assessment
- I found Matilda = Right boat, earned through wisdom I didn't have before
The only way I got to Matilda was through La Sirena.
There are no shortcuts. You cannot research your way to readiness. You have to buy the wrong boat, live with it, learn from it, and let it go when the honest assessment says it's time. Pick up what I'm throwing down here, and apply to your life where it fits. Make honest assessments, progress will come.
VI. The Framework for When to Cut and Run
How do you know when something is "wrong but worth pushing through" versus "wrong and time to move on"?
Strip away the desires, the fluff, the bullshit you added on top. Look at the facts:
Ask yourself three questions:
1. Can I actually execute this with my current resources, knowledge, and time? (Not theoretically. Actually.)
- Do you have the finances, time, energy, education, support, and drive to complete the task? Can you mentally envision the entire process from start to finish right now with what's currently at your disposal?
2. If I keep fighting for this, where will I be in 30 days? (Be brutally honest.)
- Play it out from start to finish. On a day by day basis, what can be accomplished? On a week by week basis, what are the objectives? By the end of a monthly period, what is the end result?
3. If I let this go, what path leads through to where I can try again stronger?
- The most important part of any plan in my opinion is the "EndEx Position". At the end of the Campaign, Operation, Exercise, whatever it may be, what state will I be in, and what will that state allow me to do next?
- I knew from the beginning that even if I failed spectacularly at chasing a military career, I would have picked up a number of skills that would still make me a powerful player in the game of life. It wasn't necessarily spectacular, but I only got 8 of 20 years. I did, however, learn many useful things.
For La Sirena, the answers were clear:
1. No. I couldn't fix the engine, find a new marina, and move the boat in three days.
2. Homeless in California with no boat and no money.
3. North Carolina. Friend's support. Time to regroup and hunt properly.
The choice was simple once I was honest about the reality.
Your La Sirena moment is coming. Maybe it already came and you're still trying to fix an engine that was never going to run. Maybe you're standing on the dock right now, watching the charity boat pull away, wondering what to do next. In such case, I have a different article for you.
Hopefully, you're metaphorically on a plane to Chicago to fetch your winter gear so you can then keep going, and begin to start over.
You made the right choice, now work to earn lessons and wisdom from it.
The question isn't whether you'll buy the wrong boat. The question is whether you'll have the honesty to recognize it, the courage to let it go, and the resilience to find your Matilda.
VII. This Week, Buy Your Wrong Boat
I am NOT telling you to be reckless.
I'm telling you that calculated movement beats perfect planning every single time.
Right now, someone reading this is in their version of that Chicago basement, researching their escape, waiting for the perfect moment. Let me tell you what that perfect moment looks like:
It's a Craigslist ad at 2 AM.
It's a phone call with a stranger who prays for you.
It's a plane ticket bought on faith and fumes.
It's a couple days of peace before everything falls apart.
It's the choice to let go and try again.
The perfect moment is the one where you finally move.
Your "La Sirena" might be:
The imperfect business you launch this week instead of planning for another month
The rough draft you publish instead of editing forever
The boat/RV/van you buy that isn't quite right but gets you out
The conversation that ends something that should have ended years ago
The plane ticket to anywhere that isn't here
You're going to learn more in three days of doing than in three months of research.
You're going to make mistakes. Good. Those mistakes are the education you can't buy.
You're going to buy wrong boats. Excellent. Each one teaches you how to recognize the right one.
The only unforgivable mistake is staying in the research phase until you're too old, too broke, or too broken to move.
I bought La Sirena in August 2024 with my last $4,000. By February 2025, I was living on Matilda. By the end of 2025, I'll be preparing to head south. By mid-2026, I'll be island hopping around the Gulf. Eventually, I'll make my way back to California. Then Hawaii. Then Japan. Then around the world. Then again. Then beyond.
None of that happens if I'm still in Chicago researching the perfect sailboat.
This week, buy your wrong boat.
Document what you learn. Donate what doesn't work. Find your Matilda.
Strip away the desires and the bullshit. Look at your facts. Make your honest assessment. Choose the path that leads through.
I'll see you on the water.
Per Aspera Ad Astra
Through Hardships to The Gorydamn Stars
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This is Week 4 of a 12-week series documenting my journey from the void beneath hell to ground zero just above the pit, and the frameworks that got me here. Next issue: "How I Bought The Wrong Sailboat and What It Taught Me About Starting The Journey."
If you’re reading this at 2 a.m. wondering if starting over is still on the table...it is. I’m living proof. Don’t spend another day drifting alone in darkness; start building toward the light. If you need a guide, check out my publishing hub. I believe in you, frfr, yo'.
- Isaac
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