Articles, Cruising Lifestyle

Over the last four years, I’ve worked from home. You could also say that I work remotely, since home now for my wife, Catherine, and me, is Dream Time, our 38-foot Cabo Rico.

For years, I dreamed about sailing around the world, living a life of freedom, discovery, and adventure far away from the rushed routine of our existence in New York. I wanted to live in the moment, to embrace the unexpected, and to seek new experiences in the warm, tropical, uncluttered corners of the world. But how do you make that a reality when you’re supposed to be building a career and making a living?

For the 10 years we lived in New York, I felt shackled to work by a chain of emerging technologies that all promised to make my life easier: beepers, cellphones, P.D.A.s, Sidekicks, BlackBerry smartphones. I became connected all the time. The sanctuary of Dream Time’s cabin became an extension of my office, invaded by a persistent stream of urgent beeps, buzzes, and blinking red lights.

But in 2005, while working on a last-minute project on Dream Time during our summer vacation at Block Island, in the waters off Rhode Island, I had a thought that changed the direction of my life: What if I was able to use technology—the very technology that I couldn’t escape on land—to set myself free?

I’m not suggesting that every career can be successfully navigated remotely from a small sailboat. But many can, and in my industry of advertising graphic design, as long as I have ideas and the resources to share those ideas, there are literally no limitations to how far away I can go. So we began installing the latest in communication equipment on Dream Time and after a year of researching, planning, troubleshooting, and testing,Dream Time became not only our full-time home and vessel to explore the world but also my new floating office. And in the summer of 2007, as we sailed out of Long Island Sound with the Caribbean Sea and South Pacific Ocean on our minds, it was business (almost) as usual.

Working from a sailboat is much like passagemaking. It requires planning, adjustments, and fine-tuning to reach your objective. Staying connected to the main office, especially after leaving the communications signal-saturated coastline of North America behind, became more challenging. But satellite technology is more reliable, faster, and cheaper than ever before. We discovered WiFi hotspots in some of the most unlikely anchorages of the South Pacific. We also found Internet cafés and learned about Skype, international roaming plans, local SIM cards, local USB modems, SailMail, all manner of resources to help us stay connected, no matter where we were.

Of course, working, living, and traveling in a small sailboat aren’t without challenges and may not appeal to everyone. Compromises have to be made: I’m not earning as much as I was back in New York, but then again, I’ve chosen to work only a fraction of my old schedule. Our overhead has never been lower. I connect now on my schedule, checking emails in the morning and squeezing in a few hours of work sometime between snorkeling and an afternoon nap in the hammock. I still enjoy being involved with my business, and staying connected while cruising gives me the best of both worlds. I finally found the balance that I was so desperately seeking.

Some cruisers are fortunate enough to unplug and permanently leave their offices far behind. But if you need to work, would like to enjoy just a little more time on your boat, or perhaps even set up a complete floating satellite office wherever you sail, it’s a venture worth exploring, and if it’s set up correctly, it pays huge dividends. I challenge anyone to find a better view from an office window.

So while I may not be accumulating any frequent-flyer miles, and maybe I’ll never help grow the studio into an international conglomerate working from sea, the company can boast of a satellite office in Fiji, and next year we’ll be expanding to Australia. And while, perhaps, I’ll never make the cover of Fortune magazine, it’s safe to say that while working from Dream Time, I’m definitely going places.

If you see us anchored somewhere in the South Pacific, and you just happen to need an ad layout or a new branding campaign, come on over—we’re open for business. Let’s do lunch.

Author the Author

This article was originally published in the January, 2012 issue of Cruising World Magazine and is being used with permission from the publisher.