She said, "Let's quit, sell all our shit, and move to the Caribbean!"
People think it’s the unknown that’s scary. It’s not.
Welcome, Freethinker — take a deep breath.
“Let’s quit, sell all our shit, and move to the Caribbean!”
Alisa — my wife of two years — drops this bomb just as I’m crossing the threshold from the hallway into our modern Manhattan high-rise condo.
I walk across the wooden floors and glance out at the perfect New York City sunset — rays of gold and pink wrapping pier after pier along the Hudson River. A cruise ship fades into the veil of evening shade, along with the sightseeing boats… and the mighty U.S.S. Intrepid.
I plop into the plush brown leather recliner — I’ll save the massage chair for later… after some wine.
We’re in for an interesting night.
“I take it you didn’t get it?” I ask — a question that needs no answer.
“No! This is the THIRD TIME!” Alisa is bursting.
“He said they love me.
I’m doing great work.
I earned it—
But…
Numbers are down — it’s publishing, after all.
So it’s just not in the budget.
I’m sorry.”
“Then what?” I ask. I know there’s more. The energy is different this time — not like the first two, when the promotion was promised… then pulled away.
Smiling widely, she says, “I said ‘fuck you’ to my boss.”
Okay. This time it’s real.
Do I REALLY want to quit, sell everything, and move to the Caribbean?
I give it about twenty minutes.
Just enough time to remember that my favorite part of every day — for the past five years — has been my walk at lunch.
Well… that, and complaining to Alisa about how my favorite part of my day is my walk at lunch.
She knew my answer before I did.
I walk out of the bedroom and say the three words that change everything:
“Let’s do it.”
Fifteen years later…
I know this much:
It was never about the Caribbean.
It was about the moment we stopped negotiating with a life that didn’t feel true.
People think it’s the unknown that’s scary.
It’s not.
It’s the intolerable known —
the life you wake up to every day… knowing there’s more.
So if you’re feeling like a bird in a cage…
Welcome.
This is the moment you realize the cage was never locked.
Alisa helped me find the door — perhaps these words help you find yours.
Fly free.
If this resonated, share the love with someone who could use it today.
Until next time, Freethinkers… stay present, be pleasant, and have an amazing day 🙏
Mike Messeroff
Founder of The Carpe Diem Company
Personal Freedom Coach, Creator of Self-Hospitality™, and The Extraordinary
Author of Dogs Get It: Advice I learned from my best friend