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I Sold My House to Work Remotely on a Cruise Ship for 3 Years — and I May Stay Aboard Even Longer. Here's What My Life Will Look Like. I was fantasizing about going on an around-the-world cruise. Then I saw an ad that could make it my reality.

By Amanda Breen Edited by Jessica Thomas

Key Takeaways

  • I called everybody I knew, thinking someone would say I was crazy to consider living at sea — but nobody did.
  • I'll run the digital marketing agency I co-founded while on board, thanks to my supportive business partner and team.
  • I'm excited to integrate work into my life. We're even planning a team meeting in South America.
Courtesy of Clever Lucy
Keri Witman

This as-told-to essay is based on a conversation with Keri Witman, founder and president of digital marketing firm Clever Lucy.

I've always taken every opportunity I could to travel. In college, I did an overseas study program; I backpacked around Europe by myself. But as you get older, those opportunities aren't always there. You're wrapped up in obligations. A few years ago, I decided to freelance and travel the world. Being a digital nomad appealed to me, so my friend Sara Sartarelli and I mapped out a plan to start a digital marketing agency. We landed our first client and decided on our business's name, Clever Lucy. But as business started to pick up, my idea of being a nomad kind of fell by the wayside.

Then, three months later, Covid hit, so no one was traveling at that point. And our business just kept growing. But this past March, I was having dinner with a friend, and we were talking about travel, wondering if they have cruises that go around the world, just fantasizing about what that would be like. When I got home, thanks to the magic of marketing, I was served up an advertisement for Life at Sea's around-the-world cruise. I clicked on it and went down the rabbit hole that night. It was like a lightning bolt: Oh, this is what I have to do.

Related: 'Cruise That Never Ends' May Cost Less Than Your Monthly Rent

Still, it seemed crazy. But I made an appointment with the salespeople at the cruise company. Then, on the double, I called everybody I could think of, including my parents, who always tell me I'm doing something crazy — and they didn't tell me it was crazy. I called my co-founder and business partner next. I didn't want to jeopardize our company. But she told me to go for it. Then, I checked with some clients and called my financial advisor. Nobody told me not to do it, so two days later, I put a deposit down.

"I won't have to pay for food or medical insurance...everything's included."

Since Life at Sea had just started marketing, I lucked out with early bird pricing. Double occupancy costs $38,000, but I had no interest in having a roommate in a small room, especially one I don't know — although many people are doing it. So technically if you have a solo room, you pay double that, minus the 15% discount I had. I met with my financial advisor and did the math: Between my mortgage, car insurance, utilities, et cetera, the cost of the cruise was almost a wash, and I won't have to pay for food or medical insurance because they have a doctor on board. Everything's included.

So it all just made sense. I've always loved to travel, and our clients are all over the country. Plus, there was nothing connecting me to Cincinnati other than the friends I care about. And it's a cost-effective way to see the world; I don't have to spend $1,700 on a plane ticket and pay for hotels, having to go back and forth and take time off work. I can integrate it with my work.

Related: 5 Tips for Surviving as a Digital Nomad | Entrepreneur

I grew up in the corporate world: 9-5, you had to be in the office, and I usually stayed until 7 p.m. or 8 p.m. My business partner taught me how to be more flexible. She integrates work into life; at the beginning of our work relationship, she'd be booking a hair appointment at 2 p.m., and I was like, "What are you doing? This is a work day." She's pulled me out of that corporate environment, and so many of our freelancers work that way, too. We believe that when we and our team can pursue our passions and do the things that make us happy outside of work, we're bringing way more value and productivity to work.

" As crazy as it sounds, I could see myself continuing to cruise."

I had to do a lot of things to prepare for my departure. A fantastic group of friends helped me pack up the house I'd lived in for 12 years. I also needed a new permanent address, so I got a digital mailbox; they scan all my mail so I never have to get a piece of paper again. I had to figure out which vaccines and visas I needed; I even spent a week in New York getting a Chinese visa. I sold my house and am living in an apartment with my cat, who I've found an excellent home for (and will be able to FaceTime from sea).

The cruise will leave from Istanbul in November. I'm particularly excited to see Morocco and the Galapagos and the places we'll visit in Asia because I've never been. Also, Life at Sea announced it's giving passengers the option to extend after the three-year mark, and as crazy as it sounds, I could see myself continuing to cruise. But I might want to take a break because being away from family and friends is the most challenging part.

For founders who want to take a similar leap and keep running their businesses, I think the most important thing is having a supportive team. I never would have done this if my team felt undue pressure on them to pick up the slack — because it will take the whole team to make it work. We've had to talk about what will happen if there are outages with my WiFi and how we might have to reallocate duties to ensure the clients are always first. If I have to wake up at 4 a.m. for a conference call with a client in Arizona, I will do it. I might have to stay on board to work and miss some places on the itinerary, too.

Related: How to Manage People in Different Time Zones | Entrepreneur

We've also been looking at how we can incorporate my trip into our work and keep our team and clients involved. We're even planning on having a Clever Lucy team meeting somewhere in South America.

Amanda Breen

Entrepreneur Staff

Senior Features Writer

Amanda Breen is a senior features writer at She is a graduate of Barnard College and received an MFA in writing at Columbia University, where she was a news fellow for the School of the Arts.

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