The Boat Was the Goal: What a Caribbean Story Taught Me About Leadership, Feedback, and Success
One morning, while driving to work, feeling exhausted yet energized with pre-workout in hand, I heard a story on the radio that completely stunned me.
The host was a libertarian talk show personality I used to listen to, not for life advice but for politics and occasional sharp humor. However, that day, he recounted a story that impacted me far more than any headline or hot take. It wasn’t complex. It wasn’t dramatic. Yet, it resonated with a clarity that endures.
Here’s how I remember it:
A successful CEO, wealthy, driven, always on, was finally taking a well-earned vacation in the Caribbean. For once, he wasn’t checking his email or juggling meetings. He’d rented a small boat for the afternoon, and a local captain was taking him along the coast.
The weather was perfect. The sea was calm. The stress, for a moment, had disappeared.
As they floated along the horizon, the CEO leaned back, took in the view, and said, “This…this is why I work so hard. So I can afford to do things like this.”
The boat captain smiled gently and replied, “Funny. I do this every day.”
That was it. One quiet moment. One simple exchange. But in just two sentences, it reframed the meaning of ambition, success, and freedom.
I didn’t know it at the time, but I had just heard a modern version of an old parable, the kind you find scattered across leadership blogs, minimalist lifestyle books, and anti-hustle TED Talks. However, hearing it live, casually shared on the radio, made it feel personal. It made the story real and authentic.
When Hustle Becomes a Habit
We live in a world that idolizes productivity. There’s a subtle cultural pressure, particularly in leadership positions, to keep advancing, expanding, and refining. You don’t merely grow a business; you create an empire. You don’t just achieve success; you excel.
But stories like this one ask a more unsettling question: What if we’re building structures that lead us away from the life we actually want?
The CEO in the story wasn’t wrong to work hard. He wasn’t foolish for taking pride in what he’d built. But he’d attached his sense of freedom to a future moment, to a distant reward that might arrive after decades of trade-offs.
In contrast, the boat captain had already discovered the lifestyle that the CEO was striving for, free from layers of hierarchy and daily stress.
Which raises a tough truth for leaders: Sometimes we’re so busy climbing the ladder that we forget to ask if it’s leaning against the right wall.
Feedback, Alignment, and the Cost of “Someday”
As someone who has spent years studying leadership and feedback, I perceive a deeper message in this story. I interpret this as a message about alignment.
In healthy organizations, we discuss feedback loops extensively. They help us calibrate by showing what’s working, what’s broken, and what’s drifting off course. However, most feedback focuses outward toward teams, systems, and performance.
What we often ignore is the internal feedback we get from our own lives: the tension we feel when we’re burned out, the quiet envy we sense when someone else is more at peace, the question we avoid when we wonder, What am I really chasing?
The CEO’s moment on that boat was more than just a line in a parable. It was a feedback signal and one that revealed a gap between his values and his lifestyle. He’d delayed enjoyment, convinced that fulfillment was a future event. The captain reminded him that it didn’t have to be.
And that’s the kind of feedback leaders need to hear more often, not from an HR survey or annual review, but from honest reflection.
What if your goal isn’t more, but closer?
Closer to your purpose. Closer to your peace. Closer to the kind of life you wouldn’t need a vacation from.
The Productivity Trap
We rarely question the systems we build when they’re successful on paper.
You might be managing teams, launching projects, and delivering results. But if those accomplishments come at the cost of clarity, presence, or health, what are they really worth?
The danger is that productivity becomes its own addiction. It feels good to win. We all enjoy hitting the targets we set. Everyone wants to feel wanted and in demand. But when everything becomes a means to an end, especially an end that’s always just a bit further away, we lose our ability to recognize when enough is actually enough.
And as a leader, your example matters. If you’re always running, your team assumes they should be too. If you never rest, they won’t either. And if you never question the pace, no one will feel permission to pause.
You become a culture of movement without direction. And you wake up one day on a boat, realizing you’ve spent years trying to earn a life someone else was already living.
Redefining the Goal
That’s why I keep returning to this story, not just as a cautionary tale, but as a compass.
It reminds me to define success clearly and by my own measures, not by comparison or a worldly view.
Am I working toward a life I’ll enjoy, or one I’ll escape?
Are my goals aligned with who I am now, or who I thought I needed to be ten years ago?
Do I know what “enough” looks like, or am I afraid to name it?
It’s okay to dream and lead a productive life. However, it’s also acceptable to choose a simpler path if it leads to the life you truly desire.
And sometimes, the wisest leadership lesson doesn’t come from a boardroom or bestseller.
It comes from a boat, drifting quietly across the water, reminding you that the goal isn’t always later.
Sometimes, the goal is now.
This article was also featured on Medium and Substack.
About the Author
Clayton Thompson, Ph.D., is a Colonel in the U.S. Air Force with over 20 years of leadership experience. He is the author of the upcoming book RA-RA Feedback: It’s Not a Moment. It’s a System! for building trust, accelerating growth, and creating a leadership advantage.
