Trading the Corporate Hustle for a Life at Sea

I figure I may as well kick off this blog by starting at the beginning of my journey toward less traditional work. My life on a boat is a pretty critical piece of that story, so let’s begin there.

In 2023, our family bought a sailboat. We didn’t really know what we were doing, but we did know that the post-pandemic months had left us craving something more—more meaning, more time together, more fulfillment, and more joy. These were the core elements of the new picture we were trying to paint.

At first, the boat was mostly an escape. We split our time between living aboard and exploring the East Coast of the United States and staying on land in the mountains of North Carolina. It was joyful, no doubt, but I was still working full-time in a standard 9-to-5 (or more) corporate job, and something was still missing. The boat felt more like a time-boxed experience—a getaway we'd enjoy for a while, only to return to full-time land life, sharing sailor stories at dinner parties for years to come.

But then something shifted.

We realized cruising could be more than an escape. We discovered families, couples, and solo sailors out on the water, living lives completely disconnected from corporate careers and conventional work. These people might seem like outliers to their friends and family, but they were living life on their own terms. And we knew—I knew—that’s what we wanted too.

We committed. We made the decision to live on the boat full-time. We started planning a thrilling international adventure. And I began to see that my standard 9-to-5 job—along with the promotions, the overwork, the political striving—didn’t belong with me on this journey.

So, I quit.

I decided to step off the bullet train of tech career achievement. Not because I couldn’t do it or wasn’t capable, but because it simply wasn’t what I wanted anymore. Sometimes, I wonder if it ever was or if I just thought it should be. I’ll be honest—it was terrifying. Not just in the practical ways (how will we make money, how will we manage health insurance?), but in a much deeper way. Who was I without an exciting corporate career? And perhaps more importantly, who could I even talk to about this decision?

Everywhere I looked, career empowerment groups, podcasts, and programs seemed focused on how to manage time better or achieve even more—just more efficiently. But that wasn’t what I wanted. I still wanted to solve tricky problems. I still wanted to mentor and guide other professionals. I still wanted to support my family financially. But I didn’t want to work crazy hours chasing promotions, join time-consuming focus groups just for optics, or spend all my energy on someone else’s bottom line.

Yet there didn’t seem to be a safe space to talk about that.

So, I decided to create one.

I genuinely believe we can still find fulfillment and achieve meaningful success—even if we do it on our own terms. And I believe we’re more likely to get there if we have a space to explore this new way of thinking together.

Today, we’ve left the safe shores of the U.S. entirely. We’re not splitting our time between land and sea anymore—we’re full-time sailors now, fully living aboard our boat and living out our dreams.

What’s your dream? What’s the balance you’re trying to strike between traditional work and a freer life? I’d love to hear about it. After all, I’m doing the extreme version—so there’s absolutely no room for me to judge. Let’s connect.