Throughout the spring, you may have seen a few sprigs of big changes aboard The Scallywag. We hauled the boat out for upgrades, quit our jobs, we went notably quiet on our blog.
And now, in the throes of early summer, our plan is ready to meet the full light of day: We’re casting off the lines to become full-time sailors.
While our decision may seem out of the blue, the preparation and intention behind it have taken months of deliberate work. More importantly, it’s taken a hundred conversations between Jon and myself about what we love to do, and what we want our lives to look like now and as we grow older.
Before moving to New York two years ago, Jon and I worked remotely for five years. Sometimes running a business together, sometimes working separately. This wasn’t gig economy work, but rather traditional companies that were trying a new format of working. And it worked. I completely and emotionally bought into this idea and lifestyle. It felt natural to us to pace our days and weeks around the work we needed to do and the life we wanted to live rather than a more traditional schedule.
While working this way, we lived by the flexibility to travel while getting things done. We rarely ever took vacations, but instead set up in coffee shops while we were on the move, sometimes so flawlessly that the only way our coworkers would know was by the change in background when we video chatted.
Without jobs that tied us to a place, we kept having the same conversation: where did we want to live, and what kind of people would that make us? Were we LA people? San Francisco people? Would we fit in better on the East Coast or somewhere in South America? As all our friends started to settle down, finding the answer seemed more urgent, and that’s when we bought a boat. We had a home that could take us anywhere.
Fast forward three years and we found ourselves living in New York, an amazing city where we could be anything, but only in one place. As we hit the two-year mark of residency, we were once again itching for change and we took interviews for jobs we could have only imagined being recruited for. But each time, we came home to each other and asked ourselves… then what? We have that awesome job and... then what?
The paradox of choice is a weird, wonderful and very “now” problem to have.
As a woman who wants to have kids someday, I found this indecision particularly challenging. Smarter women than I have told me the key to great work-life balance is to lock down baller job a couple of years before having kids so that you have deeper job security for your maternity leave. But a really big part of my heart wanted to build a flexible career that kids could be warmly welcomed into, rather than interrupt. I wanted to start that career before it was 9-months-urgent and continue it after, on my own time.
So the answer, for us, continues to be to pursue careers that don’t have geographic limits. It’s never been a better time to go that route — most places finally have the infrastructure to support digital nomadism and the speed with which things are changing is breathtaking. Five years ago, I got my first smartphone — in Iraq. During a recent trip to Myanmar, we learned that though the internet essentially didn’t exist there year ago, there are now more people connected via smartphones than there are houses wired to an electrical grid.
And on a recent vacation to the French Caribbean, we found pockets of internet where fellow boaters said nothing had existed just months ago.
The ability to work anywhere, and work well, is here — even if it takes extra time and inconvenience to figure it out.
This is the freedom that today’s technology provides, and yet to embrace it can still make you an implausible hire and a weirdo.
So, we’re ready to be weirdos.
We’ve launched businesses (his, mine) that allow us to do the work we love while we travel, with the assumption that there will be frequent trips to metro hubs to see our clients face to face. We’ve outfitted our boat with solar panels, a wind generator, cell and wifi boosters, we’ve upped our data across multiple networks. And we’ve hungrily read the stories of people who have gone before us to figure out just how much we can pull off without risking our sanity and quality of work.
Our plan is to sail back to California, the long way. First north, perhaps as far as Nova Scotia, then south to the Caribbean and through the Panama Canal. We don’t have a set itinerary or time span, though we think it’ll take about a year. We’re excited to explore parts of this continent and its surrounding isles we’ve never seen before, to take it slow and to make lots of mistakes as full-time cruisers.
(Our first, for example, was to set a hard date for leaving, which we promptly blew after having a camera crew see us off. ::Facepalm::)
That’s our plan. Subject to lots and lots of changes. By this time next week, we should be somewhere in the Long Island Sound, with many more stories to come.