cruising

Boat-Gazing: What visual clues show how you cruise?

When we first started looking at buying a boat, all boats looked the same to me. Some were prettier than others, but that's all I saw, and I got bored quickly.

But a funny thing happens once you buy a boat: all you want to do is stare at others. 

During our early evenings of walking the docks and taking dinghy spins around crowded harbors, it was enough to ooh and ahh at neighbor's pretty boats and gleaming paint jobs. That's still fun!

The longer I cruise, the more my boat eyes see. One of the most interesting things about observing boats is seeing what people have decided is important to them, like power, space, and adventure gear. We’re constantly boat-gazing to get new ideas for how to improve Scallywag. 

While every boater is different, you can tell a lot about a person from their boat. A little visual detective work will allow you to “read” someone’s boat to understand what commonalities you might have or where to start a conversation, or to read a harbor to understand what you're about to get into (mega money? A boat graveyard?). With practice, it’s easy to take an educated guess at your neighbor’s cruising agenda.

For others who stare at a boat and max out their observations at, "that's a boat!", it's fun to reflect on some of the easy clues boats can give off about the style and intentions of their owners. 

A full-time cruising boat, typically a sailboat or a trawler, because they’re more fuel-efficient, is equipped for distance and power. They may have yellow, red and blue jerry cans, a wind generator or solar panels.

Solar panels, wind generator, kayaks and the telltale brown smudge of an ICW moustache. You can tell we've been around!

Solar panels, wind generator, kayaks and the telltale brown smudge of an ICW moustache. You can tell we've been around!

At anchor, they’re often draped with laundry and while they can look messy, most of the things on deck can be stowed easily since they’re always on the move. That’s not to say cruisers are slobs — Many cruising boats look impeccable (especially the ones that go back to the Northeast in the summer and get a break from the intense Caribbean sun). Some will have peeling or completely wrecked paint or varnish. Longterm cruisers (including us!) often save the time and money that could be spent fixing aesthetics to cruise longer and more happily.

Liveaboard boats may also be in great or poor external condition. Because they aren’t going anywhere, they may have more on deck that isn’t secured. Bikes, DIY shade canopies, extensive gardens or additional plywood construction are all indicators that these boats haven’t made a passage recently. 

If a boat cruising boat looks perfect, it’s usually because the owner is a bit older and has had time to save up more, or the boat is in its first couple of seasons of cruising. Sailors who do 6 months on, 6 months off also have fairly immaculate boats, because they have a bit more time for improvements or repairs. 

Top left corner: Solar panels, antenna booster, wifi booster, sirius weather booster... check. 

Top left corner: Solar panels, antenna booster, wifi booster, sirius weather booster... check. 

A boat with lots of power-collecting equipment and antennas will usually indicate the owners are still working. Our own boat has never been better equipped or looked more worn on the outside. As younger cruisers, we’re not alone. If you see a boat that may be worse for wear but has new solar panels and the green glow of a wifi or antenna booster, you can make an educated guess that the person who owns it is still be working while sailing and making very strategic investments in what to improve. 

A mint-condition boat without anything secured to the stanchions, looking sleek and clean and just as the boatbuilder intended, is likely used locally or for weekends and holiday trips. Some people run their engines or generators regularly to create power, but most full-time cruisers have invested in some kind of wonky-looking equipment to keep their battery banks full.  

Trawlers, or the comfy condos of the boating world, are typically operated by coastal cruisers doing the Great Loop, heading from Maine on down through the ICW, or cruising in nearby international islands. Trawler owners are smart — the boats are spacious and relatively conservative on fuel. Owners are also typically older, with the bigger boat being a compromise of adventure and comfort. 

Charter boats usually have more than two people on them, and in the Bahamas at least, they’re usually catamarans. These boats are typically without much signage and tend to look fairly generic, save the labeling of the charter company on the sail cover or on a flag in the rigging. In my unscientific observations, if you see a Lagoon (a distinctively large brand of catamaran) there’s a 90% chance that it’s a charter, or has been in charter. 

When the sunset rolls around, we all share the same ocean.

When the sunset rolls around, we all share the same ocean.

Large fishing boats, speedboats or mega yachts rarely have cruisers on them full-time, unless they’re crew. You can often pick out a mega yacht crew by spotting groups of people walking the docks together. Six or more people, often in the same color shirt or similar clothing, is an obvious indicator that they’re crew of a big ship nearby. If you see people walking the docks who are wearing resort-wear (flowy fabrics, white linen pants) or don’t make eye contact or say hello, they’re likely passengers on a larger yacht. 

What do you look for when you boat gaze? Is there anything I missed that you're always on the lookout for?

4 mindsets for boating en route to the Bahamas.

Almost two weeks ago we finally made the crossing from Florida to the Bahamas. We are in another country! On our boat! Please, hold your applause, because I am very impressed at us for you.

When we crossed the banks of the Bahamas at sunrise the Thursday before last, Jon turned to me and said with uncharacteristic earnestness, "I can't believe we made it." He wasn't talking about the 12-hour trip across the stream, which was uneventful. He meant made it. Here. With all the variables that could have led to our failure or success. Upon reflection we realized we learned a lot about ourselves as boaters and how we fit into this larger world of cruising that we're a part of. 

Cruisers... cut short

We're a long way, physically and mentally, from where we started. We left Maine at the beginning of September and it took us until December to make it to the warm climes of Florida. Not just because our boat goes 6 miles an hour, but because Jon and I have been hard at work building up our businesses and have been flying to clients every few weeks. Then there were the holidays, when we returned home to LA for work and family for an entire month. Boat after boat of people we'd met along the way passed us and made it to the banks of the Bahamas, their Instagram accounts crowing victoriously about warm turquoise waters while we scraped ice off our decks in New Jersey, Virginia, North Carolina. 

(Honestly there's nothing more aggravating than seeing people you've just met a few days or weeks prior get to your destination before you. It's the same feeling I get as when I hear about mean girls from high school being successful and happy as adults. It's just not fair!)

Then, somewhere around our downward pass through New York, we went from cruising to delivering our own boat. The weather was getting colder fast, and the way south more and more complicated.

On the East Coast, more than a century of ferry and barge traffic shaped what's known as the Intracoastal Waterway (or ICW for short). The ICW technically runs all the way from Massachusetts down to the tip of Florida, comprising more than 3000 miles of inland natural and manmade canals. Together, they allow you to run the length of the eastern seaboard protected from storms and waves. 

While the Cape Cod Canal, which we passed through during the summer, counts as part of the ICW, the real action doesn't happen until around the tip of New Jersey, during which time most boaters who haven't already ducked into the Jersey ICW turn into the Chesapeake and then make their way through what might be the most traveled area of the ICW, the cut through Virginia and North Carolina that circumvents Cape Hatteras. 

Once you hit the ICW, there are a lot of factors to contend with: Do we take it at all or go for multi-day trips "on the outside" and knock out hundreds of miles at a go?  (We ended up doing five or six overnights, as long as 48 hours, to get down the coast after taking the ICW through to Georgia). Will the tides allow for the draft of our boat to transit without running aground? (probably not, if we're asking this question.) If we follow those buoys will we run aground? (No. Five times running aground later, we now know to follow the damn buoys and don't pay attention to anything else, including our charts and other boaters.) 

Captains on delivery (of our own boat)

This is where we somehow turned into captains delivering our own boat... to ourselves. The days were long and stressful, waking up in the pre-dawn and motoring as far as we could before sunset, as the ICW is impassable after dark (there are just too many ways to hit something.) Overnights were easier and got us places faster, but it took me several trips to get over an unfortunate incident off the coast of Jersey that had us caught in 10-foot waves for a good 12 hours. (See image below which speaks for itself. OMFG).

Somewhere between New York and North Carolina, we were no longer sailing. We were motoring, hustling, hurrying and, speaking for myself, generally hating life. It's pretty hard to rush on a boat to begin with, but with temperatures dropping, we didn't have much choice. 

Freezing weather and grueling schedule aside, the ICW is a fascinating slice of America. Apart from passing through tiny, historic towns that you'd never otherwise see, to transit the ICW is to be a part of a massive yearly exodus from north to south, in which thousands of boats participate every year. 

The snowbird boaters

As we worked our way farther south, the weather warmed again. It gave us a chance to meet some new people, boaters who weren't going past Florida. Surrounded by folks like these, cruising started feeling even more distant to us. These snowbirds, who began to drop off the route as they found their winter slips, didn't feel like the same folks we had run into in the far north. Their boats were lovely and portable condos, and they hold both an untouchable regard and innate fear of cruising to farther regions. Many of these folks never see the Atlantic -- I spoke to several people who had done the entire trip from Virginia down and never touched "the outside" but lived on their boats half the year or more. Others had 2, 5 or 7 year plans for crossing the Gulf Stream and cruising the Bahamas, which runs a mere 4 miles or so off the coast of Palm Beach. 

Their lists were long -- lists of reasons why they couldn't go yet, and why we should be concerned about going now. Lists of things our boat and their boats needed to have. All of these lists were passed along with the greatest of kindness. It was lucky that we had come this far, or their concerns would have shaken our confidence. It's easy to see how so many people end up in the boatyard for months at a time at the precipice of the Caribbean.

The white wine cruisers

And then suddenly, we were in the Bahamas. We were suddenly here, with no plans except to follow weather and sites that we wanted to explore. We're happy to call ourselves cruisers again.

But something curious has happened since we've arrived, and I can't help but notice and point it out. Somewhere across the Gulf Stream, it became detestable to work. Or rather detestable to others that we still have to work. 

It feels extra odd because of the number of people we've met in getting here that were working toward something: buying their boat, making their 5-year plan to leave, waiting for their kids to go to school so they can set off. We've arrived at the end destination, so to speak, and it's as if no one wants to be reminded about how they got here.

(Surely part of this is due to the fact that we're working on our laptops in the middle of everyone's vacation. Nobody wants to be reminded of the work they left at home.)

But as I work from a diner-cum-liquor-store in the mornings, I find myself getting scolded by cruiser after cruiser to "put the laptop down". One southern fellow, (whom I've taken to calling Foghorn Leghorn), has ranted at me multiple mornings in a row in an exchange that goes something like this:

"Honey, you're a real gigabyte girl aren't ya? I'mma give you five more minutes before I take them gigabytes away so you go outside."

I explain that I have to work so I could enjoy all the island had to offer.

He stares, wide-eyed, unsure how to answer. Then he yells, "Honey, good luck on the gigabytes!" and then walks away, slamming the screen door behind him.

An hour or two later, as I'm walking back to the boat, he pulls up in a golf cart next to me:

"Honey, you get all those gigabytes in?"

"Yup, I got all the gigabytes," I tell him, as he steps on the gas and putters away.

Returning to the boat, on the first day of said exchange, I passed six boats on the dock. Four of them had owners in their cockpits, sharing a bottle of white wine with each other at lunch. Like us, these white wine cruisers no longer have a transit schedule to keep, or a weather window to catch, per se. But they have literally no other demands on their time, and as such look at us as we pass like odd foreign creatures with our laptops and conference calls. We're all cruisers, but once again I'm beginning to realize we're not all the same. 

To try to keep a normal schedule in the face of such luxurious temptation is a challenge. I always thought that the hardest part of cruising would be working, not the peer pressure to stop working.

As of yet, we haven't met anyone in the Bahamas that is our age or working while they go. But we've only just started exploring the Abacos, so I'm sure we'll come across like minds soon. 

As for what we'll call ourselves, I've sort of warmed up to the term Gigabyte Girl. What other nicknames have you heard for cruisers like us? I'm sure that Killjoy is on the list! 

 

A beginner's guide to working full-time while cruising.

It’s been almost exactly two months since we set sail away from New York and some days it feels like we left two years ago. We have quickly found a routine for working and play, just as we did on land. And we’ve slowly eked a path up the east coast to Maine, bay by beautiful bay. 

A few nights ago, as I sat in the cockpit of the Scallywag, waiting for meteors to streak the sky, I felt deeply appreciative of the luck and persistence, as well the ability to work from anywhere, that got us here, under a carpet of stars in Boothbay Harbor, with our dog obsessively licking my arm. (Way to kill the romance, Honey.)

Sometimes when I wake up I can’t imagine what our old life feels like anymore. This new one has surprises and challenges for us every day, both personally and professionally. As I’ve calibrated to life as a full-time cruiser, I’ve also had to make some significant adjustments to how I work. 

I thought I’d share what works for me and how I manage my business so that it might help anyone else out there that’s wondering if they can hack it professionally while sailing. 

A remote working preamble

I’m not new to remote working. In fact, I'm somewhat of an expert in it. Part of what I do for a living is help advise other companies on how to structure and manage remote teams. In years combined, I’ve traveled while working in some form for the majority of my career — from my apartment in LA and from tea houses in Iraq. On my best days, I’m an easygoing and flexible person, which makes working in a different place every day fun, if not always easy.

But working while traveling isn’t for everyone. As a manager, I’ve run remote teams throughout my career, including growing a remote editorial team of 4 to more than 50 people, and saw all kinds of ways that working by yourself from weird locations can wig people out. I also became an expert what kind of behaviors created great remote professional relationships and what didn’t. I'm also pulling together a list of further reading that I'll post separately. 

Get into a groove before you go

While this work style isn’t different for me, I am a new small business owner. Three months before we set sail, I opened my own company, which was the culmination of content strategy work I’d been doing for years. So while we were prepping the boat for launch, I was also locking down contracts, incorporating the business, setting up its digital infrastructure, contracting freelancers and delivering actual work regularly. 

To put it lightly, I don’t recommend that timeline. For those three months, I worked 14-hour days and then went home to boat work. Sometimes I worked in the middle of the boat work, asking Jon to stop sanding something so I could jump on a conference call. 

When we had to go on the hard for a couple of weeks and our boat was on blocks in a signal dead zone, I had to commute to a coffee shop by climbing down a ladder with my laptop and walking 20 minutes just to check email. I thought I was going to die. Don’t be like me. Give yourself more time to get your boat and business ducks in a row before you leave. 

Change one thing at a time

There’s an old piece of advice that says you should never move, get a new job and get married at the same time. Funny enough, Jon and I did just that when we moved to New York, and we survived. But the principle remains true. While those last three months before taking off were murder, our overall timeline for cruising was unintentionally a much longer one. We bought our boat three years ago, without knowing how to sail it. In that time we’ve almost always lived on it half the week, and spent plenty of time learning how to operate and care for it. 

Lifestyle-wise, splitting our time between boat and land was a luxury of our apartment’s amazing rent control, but the idea of easing into things is one that I think can be applied universally. Eleven months ago, we moved onto the boat full-time, worked out the kinks of full-time life aboard when the boat was forcibly docked until spring, and had a chance to play around with alternative sources of power and internet while having access to electricity and wifi close by. 

Even the dog had a chance to settle in and figure things out. 

By the time we shoved off, the only things we really had to nail down were our pace and our routine, as well as what life was like primarily at anchor or mooring ball. 

A photo posted by Sail Me Om (@sailmeom) on

Consolidate your schedule and your days

Even before leaving and as soon as you do, start thinking about setting blocks of time for work and calls. It helps to hold days adjacent to the weekend in particular, so that you can have time to catch up between sailing days. Set your calendar availability accordingly, so that you know you’ll be truly “off” when you’re out sailing, and that you won’t have to put out any last-minute fires. It can help to put an away message up for particularly long sails or for weekends when you’ll be more likely to be off the grid. Don't feel guilty about not always being immediately available. I’ve found that as both manager and managed, being clear about your availability and doing your work accordingly is way more important than the number of hours you’re perceived as being available. 

Plan your work around your internet connection

This goes for daily work, and the type of work you do. When I started my business, I moved the focus of my work away from daily people management even though I loved it, because I knew I wouldn’t be able to be as hands-on with employees as I am when in one place. The people I do hire as contractors are mostly people I’ve worked with before and have a proven track record of reliability and autonomy. I pay them more so that I can set them free and not worry. That’s a really valuable investment in itself. 

Professionally, I pick clients and contracts that have predictable timelines for turnaround (so no more breaking news work), and while I prefer to do video chats instead of conference calls, I’ve found that video is almost impossible to support without advanced planning. So choose your communication methods wisely. 

Blocking chunks of time for work and sailing will allow you to get to a strong internet connection for things like file transfers and heavier usage tasks, like video calls or video editing. I like to plan these things for the morning, so that I have a chance to work a little more loosely in the afternoon, but also most coffee shops are open early and can close as early as 3 pm. That coincides nicely with my energy low periods, so if I work 7:30-3, basically all my work is done and I can get a change of pace when I can't stare at a screen any longer. 

This sometimes means you have to choose to drop anchor in more populated locales than you'd like, so you can be sure to get a signal. Hardcore cruisers might scoff at this, and it's true, I've mourned the deserted islands we haven't been able to hang out on for days on end. But to us, being able to cruise and dropping anchor in a slightly busier port to get work done is way better than staying home. So we save off the grid cruising for weekends. 

Learn the coffee shop circuit

The digital nomad’s coffee shop usually isn’t the trendiest one on the block. You’ll need open tables, open wifi, and open wall sockets, so that you’re not constantly draining your boat battery. Picking one a bit farther from the main drag and ordering a large order early in the day with a generous tip will ensure that you’ll be able to sit for hours undisturbed. If you're on calls, avoid cafes that specialize in smoothies and other blended drinks. Seriously. Starbucks, with its Google internet and Frappuccinos, is a blessing and a curse. 

When arriving at a new place, I always check the internet connection on my phone while waiting in line, so that I don’t end up ordering a full breakfast for goodwill credit and end up without a connection. 

Perfect your mobile office

Invest in your gear. It is the difference between work-life happiness or not. I’ll get into this in a later post, but my must-haves are a super fast, souped up computer, noise-cancelling headphones as well as headphones that cancel background noise for calls (Apple’s seem to be the best at this), an a/c and d/c charger for my laptop, a waterproof phone case with an extra battery built in so that I get twice the normal battery life, and extra internet via iPhone tether and separate hotspot. When coffee shop wifi clunks out during a conference call, I’ve swapped onto a backup method seamlessly enough that no one even notices. 

Transportation is important too. We have foldable bikes that pack up so small I can ride to a coffee shop and tuck my bike under the table while I work so I don't ever worry about it getting stolen. Being able to carry my "car", and my "office" with basically no hassle in and out of a cafe makes me feel like a real badass. 

Have backup internet

Aboard Scallywag, both our phones have enabled tethered hotspots, we have a Verizon hotspot, a wifi booster to make any open signal stronger and a cell booster to get better reception. We cycle through all of these on a daily basis. Internet needs are different for everyone, but I highly recommend this kind of system if you have to make sure you're always connected. Even then, you have to pick your ports carefully, the more off the grid you go.

Our friend Kim takes care of business at the wheel while I practice awkward hand gestures.

Be wildly reliable

This goes without saying but I’m saying it. Working remotely does not give you license to be less professional. Once, I had a newly hired employee that decided her first three weeks of work at a remote company should also be when she took a three-week road trip across the U.S. Her job lasted two weeks before I fired her. This is also why, when managing teams, I put a ban on moving cities during the first two months of employment for my employees at the distributed company I managed them at. If anything, you have to work twice as hard and communicate twice as well to achieve the same result while working remotely.

Luckily, If people trust you, you’ll be surprised at how overwhelmingly supportive they will be of your unusual lifestyle. But you have to build that trust. If you do it well, your cruising life will become its own marketing tool. Every professional call I have starts with the person on the other end asking where I am and how I work on a boat. I’ve gotten business referrals from people in back in New York talking about us pulling this off. If you do it well, this lifestyle will do you well.

Apply your hourly rate to your own time

I’ve met a lot of cruisers who go out of their way to save money by investing huge amounts of their own time or inconvenience. But there’s a break even point where, when focused on your work instead of your schemes, you’ll make more money by picking the more expensive or easier path. If it’s a choice between a mooring with a strong internet signal or a free anchorage way across the bay with none, it makes more sense for us to pick the more expensive option because we have more time and ability to work effectively, and our hourly rates are higher than the cost of a daily mooring ball. This applies too, though less often, with boat work. We fix almost everything ourselves, but we will invest in someone to teach us something new or do a menial task for us if it will take us an insane amount of hours to do it ourselves. It is more cost effective for us to spend that time working our real jobs to pay for someone else's help and have money left over. 

Have “a guy”

Following that principle, sometimes, when you’re in the middle of nowhere, you just need someone to handle stuff for you. I employ regular contractors, for the most part, so there aren't many moments where I don't have the time to handle my own work, but I do have go-to contractors I know can turn things around in short notice, and one amazing guy who can do preliminary brainstorms for my business or research how to handle mail delivery on a boat, without qualm. I have an apartment manager who handles any issues in our apartment back in LA and friends I pay to jump in, in a jiffy, if I don’t have the time for a quick-turnaround data analysis. Figure out which things in your life are most vulnerable to last-minute needs and know who your people are to turn to before you go, both professionally and at home. This'll save you from ruining your day or your plans and make sure that your clients and your crew stays happy with you. 

While we're at it, get used to the fact that you will need help professionally and personally but as mentioned above, if their hourly rate is lower than yours, it makes sense for your sanity and pocketbook to ask for help every once in a while, even if the help you need is more personal errand than professional. 

Set expectations with your crew

There’s nothing more stressful than trying to finish work on a trip while everyone’s waiting for you to go do the fun stuff, right? That’s what cruising while working is like all the time, if your crew doesn’t understand how you need to work to be effective.

Share your schedules, have open and frank conversations when things are working or they’re not — for example, I get super anxious if Jon wants to sail to a new destination before a block of conference calls later in the day, because I like to make sure I have a strong cell connection and a quiet place to talk. After a few close calls, I asked that we always have several hours between our estimated time of arrival and those calls, so that I’m never trying to do work on the run.

Jon and I are often asked if we drive each other crazy, since we work and live all in the same small space. The answer is, thankfully, no, but that’s because over time we’ve developed tactics like this for being able to be alone, together, especially while working. 

Like on the high seas, respect your crews’ requests or concerns when they voice them. 

Find time for reflection

Let it be said that cruising and working is not a working vacation. It’s exhausting, especially in the beginning as you’re figuring everything out. It’s easy to pack every single day with something to do — emailing, fixing things on the boat, sightseeing — and in our case, several weeks can go by without us taking the time to pause and consider what it is we’re doing with our lives and appreciate it. 

Reflection can come in a variety of ways — a blog, a logbook, a conversation of highs and lows over dinner, but make space to keep a record of your journey and your thoughts, and don’t let that fall to the least important thing on your list. Years from now, you’ll thank yourself for it. 

Do you have a strategy or tip for how you handle working remotely, or have a question? I'd love to hear more. 

 

We're leaving New York for a life of remote work and sailing adventures.

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.