Our Inaugural Man Overseas Retreat in Costa Rica was an immersive experience blending self-improvement, emotional work, and practical life strategies, all within a brotherly, supportive setting.
Each attendee left with more tools to equip themselves with the mindset needed to achieve anti-fragility—a concept developed by one of my favorite authors, Nassim Taleb. It refers to the ability to not only withstand any stress, but to thrive in the face of uncertainty and change.
Anti-fragility is different from resilience. If a man is resilient, he will bounce back quickly from failure.
But when a man gains strength through adversity—battling chaos & disorder valiantly and improving himself as a result—he is stronger, more knowledgeable, and a more capable version of himself.
The man I just described is anti-fragile. He’s become unfuckwithable.
We discussed preparing for a crisis before it comes. Because it’s coming.
Tragedy is built into the human experience. If you doubt this, consider that everyone you know will disappear someday.
But you can’t set a clock to it. Because you don’t know when it’s coming. Yet, unexpected hardship falls on us all.
This life will punch you in the fcking face—not to think so is naïve. I’ve personally had the proverbial rug pulled from underneath me while getting punched in the face at the same time.
More than twice, actually.
Emotional Work
Who knew getting a bunch of stud guys together in the most serene and intimate setting—a secluded villa overlooking the Pacific Ocean—would be a transformative experience and add “fuel to their fire.”
But that’s what happened.
Man O Retreat was designed to foster self-development and purposeful living among men. I’d planned group meditations, prayer, gratitude circle, etc. But we achieved so much more than I’d hoped.
I’ll use this example to illustrate my point. When I watch a movie or read fiction, I want to not only learn something, but be taken on a rollercoaster of emotions. I’m giving you my attention for an hour or two, now take me high and low…
I want an ab workout from laughing so hard. Teach me something. Then ten minutes later, get me all verklempt and faking like I need to use the restroom so nobody can see how red my eyes are.
Well, I’d asked each attendee to give a 20-30 minute talk to the group—told them it could be about anything—the goal should be to educate, elevate or entertain us. Sound familiar?
Since there’s no more important skillset than the ability to communicate effectively, I knew this sort of practice, in a friendly setting, where you can get candid feedback afterward, would be invaluable (and enjoyable).
The individual talks were exceptional. I’d flown a videographer in to capture the best parts of the trip—he has footage I hope to share soon.
Each attendee was well-prepared to speak. And each of them killed!
More important than the will to win is the will to prepare. – Charlie Munger
I’ve never laughed so much in my life as last week. Nor have I ever seen so many grown men cry. We had dudes—myself included—sharing their deepest, darkest secrets [without judgment] that left them speechless at times.
Practical Life Strategies
When I’d wake up in the morning at 6:30am, I’d see guys in the midst of their morning routines. They were working out, doing breath-work, grounding, or drinking coffee. Come to think of it, it may have just been me having coffee.
As a collective, the day didn’t start til our 7:45am group meditation, followed by everyone sharing their meditative experience and how to better control the monkey mind. These group discussions got so good we’d show up for breakfast 15 minutes late.
But we stuck to the itinerary as much as possible. I’d see the guys talking outside by the pool and yell, “Fruit Cakes, it’s time to do X!” Because, you know, even confident young men should be humbled from time to time.
All meals were provided by an excellent chef who not only put up with our hangry requests everyday, but allowed me to practice mi Español. Mi gusto la fruit y la carne. Pero no juntas amigo. Yo es no loco.
Of all the meals we shared, the hikes, fishing excursion, games played on a felt table that were dominated by D’Albor (he went 10-1…”1″ to the host:), maybe my favorite part of the trip came from my asking each attendee for their “emergency contact.”
What the group didn’t know was I’d use their emergency contact’s info to ask for a handwritten letter about the guys, to be read aloud after their respective talks.
It was powerful stuff. And brought more tears.
We each confronted our past to see what we can learn from it, and learned effective methods to discard those aspects of our past that no longer serve us.
During my talk (I went first), I shared that without my relationship with God—a connection to the divine I’ve cultivated since I was tiny—without the deep love I have for my family & friends, I wouldn’t have made it through my personal hell on earth.
For some, the exercise was cathartic. One attendee said they were sharing an impactful event in their life they’d never shared before. And they appreciated the opportunity to “work through” a life-altering event they’d never really confronted, much less verbalized.
Afterward, I asked everyone to write 2-3 things each speaker did well, plus 1 thing they could do to improve their talk. That way, everyone would receive anonymous feedback.
BIG THANK YOU
For the rest of what we did, you’ll need to attend next year to find out. I’ll challenge myself to make the Retreat even better in 2026.
Thank you to everyone who made the trip. You used last week in Costa Rica as an opportunity to connect with like-minded men, improve your communication skills, and gain a clearer perspective of what building meaningful relationships and a more purposeful life looks like.
I couldn’t be more impressed with your clarity and confidence. And I couldn’t be more grateful you’ve chosen me to help with your roadmap toward LIVING a BIGGER LIFE!
Iron sharpens iron.
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