Way Out #1: Corporate Ladder to Costa Rican Freedom with Mike Messeroff
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What if you had everything you ever dreamed of, and you were still miserable?
From Corporate Climb to Island Hopping
Mike's awakening started with a simple realization: the best part of his day was his walk at lunch.
"That’s not okay," he thought. Despite a good job at JetBlue with great perks and leadership, something felt off. His wife’s frustrations with her own stalled corporate career pushed them over the edge. They sold everything, left Manhattan, and moved to the Virgin Islands. Mike supported their lifestyle by bartending and using their savings to fund travel from one place to the next. They were scrappy, intentional, and willing to bet on themselves.
As Mike says in our podcast discussion, “I lived in the Caribbean for a year. I traveled to Fiji, Indonesia, Hawaii, all over Australia, all over New Zealand, and then we ended up in Breckenridge, Colorado. And I was miserable!”
What Mike discovered was that changing your zip code doesn't change who you are. The real shift came not from where he lived, but how he lived.
The Real Wake-Up Call: Skiing Through Depression
After landing and settling down in Breckenridge, Colorado, Mike expected to be the happiest he’d ever been. He was living the dream life he thought he’d always wanted. He was skiing 100 days a year, had a loving wife, a great job with his best friend, a beautiful puppy, and lived in a town that looked like Christmas postcard.
And yet he hit the lowest point of his life.
As he says, “ At that point in my life, I was in the lowest, darkest, deepest depression. And I was confused, you know. I had already quit corporate. I had done all the things that I think everyone would want to do, travel the world and have a lot of fun and see amazing sites and then live in a ski town. I needed that visceral wake up call because it taught me that happiness is not in just quitting. It's not in skiing every day.”
Mike also shares that he almost lost his relationship with his wife due to his behavior.
As he put it, “I was an asshole. I wasn't compassionate, empathetic. I was not the person I am today. And I knew that something had to change. And the only thing that I knew of at that time was therapy.”
Mike’s true metamorphosis began through therapy and mindfulness. Fortunately, his therapist introduced him to meditation, and the Headspace app became a daily ritual for him. That internal shift changed everything for Mike.
From Self-Healing to Guiding Others
As Mike transformed, people noticed. Friends started asking what he was doing and why he seemed so happy. What started as simple coffee chats turned into hours of deep conversations. He realized he had something valuable to share: a way out of the soul-sucking grind. Coaching emerged naturally.
Mike says he never set out to be a coach. He just knew he’d suffered and grown, and that he could help others do the same. Today, Mike works primarily with executives in hospitality and adjacent fields, helping them reconnect with themselves, break from toxic patterns, and find peace.
The Myth of Retirement and the Power of Now
My interview with Mike was so inspiring. One of my favorite philosophies that he shared is that “Retirement is a Myth.”
He says it is a hoax, and a "huge lie that literally steals our lives away from us."
“We get really good at what we practice. And if you spend your lifetime practicing deferring joy, you get really good at deferring joy.” Mike thoroughly rejects the idea of deferring joy.
Instead, he teaches clients to power up before they enter their workday by filling up their own cups first. And of course, he practices what he preaches. For him, that means meditation, breathwork, movement, time in nature, and deep presence—every single morning.
He says he takes anywhere from six to eight hours for himself every day before he enters the world.
His biggest flex? Starting work at noon and pouring from a full cup.
Money, Meaning, and Self-Worth
Mike’s income today surpasses what he made in corporate, but it didn’t start that way. From bartending in dive bars with no experience to slowly growing a coaching practice through word-of-mouth, Mike’s journey was built on faith, grit, and generosity.
He continues to reinvest in coaching, spiritual practice, and his clients. The result is a deeply aligned life and a growing community.
His message is clear, and we should all listen: success isn’t something you get from the world, it’s something you bring to it.
Healing Generations: Why We Deserve Joy
Another of my favorite philosophies that Mike shared was how his family’s history shaped his ideas about work, money, and self-worth. His father moved across the country when Mike was only seven years old to pursue a career that traded time for money. His mother, meanwhile, modeled scarcity, constantly comparing herself to others, and constantly saying no to things she felt they couldn’t afford.
Together, his parents taught him two different sides of the same message: joy is earned through sacrifice.
It wasn’t until his mid-30s that he realized how deeply those patterns were running (and ruining) his life. Through mindfulness and reflection, he reframed that story. This is absolutely one of my favorite parts of our conversation, not least because it is so game-changing, and it reframes the hustle-and-grind mindset so endemic to our culture.
“Our parents were brought up by their parents who went through the Great Depression. I mean, they had to stand in line to get bread. You had to go through that so I could be free. I don't need to keep on perpetuating these cycles of working for tomorrow and saving and hoarding, but you did.
To me, it's almost literally a slap in the face to your entire lineage of like, hey, you guys suffered for generations, hundreds if not thousands of years, to get me to this place where I could truly enjoy my life. I could sit on a beach and meditate and cry tears of joy because I'm free and I get to watch the waves and the birds and just enjoy life. And if I didn't do that, then that is just slapping them in the face and saying, hey, like whatever you did for me, I'm not even taking advantage of.
I'm going to enjoy my life. I just, I feel passionate about it. That's the reason that we're here. That's the reason for evolution.”
My takeaway from this, which I am working to embody every day, is that we don’t need to carry forward generational survival patterns. We don’t need to hustle or grind our lives away. We are the generation that can embody joy.
The Self-Hospitality Collective: A New Chapter
Mike’s next big move is his creation of a new community called The Self-Hospitality Collective. It is a free (and eventually tiered) community for hospitality workers seeking relief from burnout. It’s a space to exhale, connect, and grow.
He also writes a beautiful Substack newsletter, The Circle of Free Thinkers, filled with poetry, reflections, and grounded wisdom.
Mike’s Advice for Wayfinders?
If you feel stuck, anxious, or numb, Mike says congratulations. It means your internal guidance system is working.
“The nudge becomes a shake. Then a little discomfort becomes depression. And that's fine because we all need those alarms.”
His top tools:
Meditation (even 3 minutes a day every morning)
Mike swears by the simplicity and power of short, consistent meditation. Try using an app like Headspace or Insight Timer and commit to just three minutes first thing in the morning. Sit still, breathe, and focus your attention on the present moment. Over time, this small practice rewires your nervous system and makes space for calm awareness.Gratitude
Start or end each day by writing down 3 things you're genuinely thankful for. Don’t overthink it. The sun on your skin. A good laugh. Clean sheets. Gratitude isn't about toxic positivity; it’s about training your brain to notice the good that’s already here.Presence before productivity
Instead of waking up and rushing into to-do lists, Mike recommends pausing to check in with yourself first. Ask: How do I feel? What do I need? What kind of energy do I want to bring into my day? This helps you lead your life intentionally, not reactively.Journaling your ideal day
Write out a few sentences each morning about what your ideal day would look like if you were already living the life you want. Who are you with? How do you feel? What are you doing? Let it be specific and sensory. Over time, it helps align your actions with your desired future.
One of Mike’s favorite quotes, by American poet Mary Oliver, seems to encapsulate his worldview. “Joy is not made to be a crumb.”
Follow Mike
📲 Instagram, TikTok, and more @mikemesseroff
If you’ve ever wondered whether there’s more to life - there is. Mike Messeroff is living proof that with presence, courage, and persistence, freedom is not just possible: It’s your birthright.
This post is part of the 101 Ways Out series: stories of people who found the courage to exit the status quo and build a life of purpose, freedom, and joy.
