Episode Description
I spent my last $4,000 on a sailboat I found on Craigslist. The engine died 48 hours later, and the marina wanted her gone by Friday. It was the best decision I ever made.
This is the story of La Sirena: the wrong boat that taught me how to find the right one.
Follow me from my escape from Chicago with next to nothing, making a bet that looked reckless but was actually calculated, and learning that starting wrong is infinitely better than staying paralyzed.
If you’re stuck in the research phase of your escape, your business, your move...this one’s for you, Beratna.
and do kindly leave me a review if it resonates!
What You’ll Learn
My “La Sirena” Story:
* Why I bought a sailboat sight-unseen with my last $4,000
* The 48 hours of peace before everything fell apart
* How a seized engine became my best education
* The framework I used to decide when to cut losses vs. push through
The Starting Wrong Philosophy:
* Why “the perfect boat doesn’t exist” applies to everything you’re planning
* How buying wrong teaches you how to get right
* The difference between reckless gambling and calculated movement from desperation
* Why staying in research mode is the most dangerous position
Your Framework for Action:
* The three questions to ask when deciding to pivot or persist
* How to strip away desires and look at facts honestly
* Recognizing your own “La Sirena moment” in real-time
* The pattern: Wrong boat → Honest assessment → Right boat (through wisdom earned)
My Favorite Quotes
“I didn’t want to risk everything on one bet, but staying in Chicago was guaranteed failure. Moving to California was only probable failure. When you do your math honestly, sometimes the ‘reckless’ choice is actually the most calculated one.”
“Starting wrong teaches you how to get right. Staying paralyzed teaches you nothing.”
“The only way I got to Matilda was through La Sirena. There are no shortcuts.”
“You’re worried about making a mistake. I’m telling you the mistake IS the education.”
“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.”
Resources Mentioned
* La Sirena: 28-foot sailboat, Dana Point, California - The wrong boat that taught everything
* Matilda: Current home, North Carolina - The right boat earned through wisdom
* The Framework: Three-question decision matrix for when to pivot vs. persist
* The Pattern: Chicago basement → La Sirena → North Carolina → Matilda → The world
Action Items
This episode is about movement. Here’s what to do:
* Identify your La Sirena - What are you researching/planning/optimizing that needs to just START?
* Run the three questions - Can you execute with current resources? Where will you be in 30 days fighting for this? What path leads through if you let it go?
* Make your honest assessment - Strip away the desires and bullshit, look at the facts
* This week, buy your wrong boat - Take the calculated risk that looks reckless but beats staying paralyzed
Dive Deeper
Blog Article: Read the full written version at TheIsaacLester.com
Newsletters: Did you know that I have other projects on Substack?
YouTube: Watch the video version at @TheIsaacLester (coming soon!)
Community: Join the conversation in Lester’s Legion on Skool (coming soon!)
About The Isaac
Isaac Lester is (just a humble man, trying to make his way in the universe, yo’) a Marine Corps veteran who went from his mother’s basement to living on a sailboat while building a digital empire. He, me, … I, document, my, entire rebuilding journey: the systems, the struggles, the frameworks that actually work when you’re starting from nothing.
Currently living aboard Matilda in North Carolina, preparing to sail south and eventually around the world while teaching others how to escape, rebuild, and create freedom on their own terms.
- Isaac
