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We moved to Puerto Rico... And bought a house. Here's why.

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It's three weeks into 2018, and I'm scared shitless.

We've filed all the paperwork. We've moved to Puerto Rico, and there's no turning back.

We're officially homeowners. We have a mortgage! In a hurricane-ravaged country, with businesses that depend on convincing people we're really great at what we do from thousands of miles away. We've sunk all of our savings into a gorgeous, needy, 200-year-old mansion in an uncertain housing market.

I'm told everyone feels really excited and a little bit nauseous when they buy their first house. 

In addition to being scared, we're also thrilled. Some of you who know us or have been following along on our journey, know the latter half of 2017 hasn't been easy. After being hit by two hurricanes, we are exhausted. Scallywag is looking worse for wear. She's floating, and will be dreamy again one day, but for the moment, our boat home isn't liveable. And our paltry insurance payout means it will take a lot of our own sweat equity to get her back into fighting shape. 

Jon and I decided, a few days into taking respite from post-hurricane rebuilding in our hometown of LA for a few weeks, that our plan to sail back to California just didn't feel like the right next move anymore. Despite everything, we missed Puerto Rico and all it offered us. And we wanted to make a permanent home there.

Why Puerto Rico?

We never planned to cruise full-time forever, but we also never want to give up on cruising. Working while traveling can be murder on you, physically, mentally and tax-return-ally. So we've been looking for a place to base ourselves during our entire trip from New York to Maine and back down. We found towns we fell in love with, but we just couldn't see ourselves staying there. And then we arrived here for hurricane season.

Puerto Rico, specifically San Juan, checked a lot of boxes for us:

-It is a friendly culture that welcomes new people

-It has a ton of great art and lively activities

-The food is killer

-It's beautiful and historical

-There are universities and art schools nearby (we realized all our favorite places had access to a great school.) 

-It's near an ocean 

-It's warm!

-The music is awesome

-It has a strong liberal and progressive community of locals and expats that we feel comfy in. 

-It's still U.S. territory, which makes it easy to relocate our work, but feels like we live in a magical distant land with castles.

-There's an awesome tech community

-There's a major airport just 15 minutes away with cheap flights to lots of cool places.

-Real estate and cost of living is affordable and awesome

-Cell reception and internet are rock solid (when no hurricanes are nearby)

-It's a place where the money we spend matters and contributes to an economy that needs it.

Those are personal reasons we looked toward San Juan, but we can't talk about moving here without talking about how Puerto Rico has been in the news A LOT lately: For its booming tech scene, great tax incentives and its post-storm utilities nightmares. Also for the crypto bros who are moving in by the minute. And for its fight to become a state and the fight for decolonization.

The last few months have intensified all those stories. People are making real choices to commit or to leave.

As stalwart institutions fold, new ideas, businesses and newly arrived friends are also blossoming. In short, after the hurricanes, things are getting better here... and they aren't. There's a lot of awfulness to be had, and half the country is still without electricity. It's a strange, uncertain place to be at the beginning of 2018. 

But it's an interesting place to be, and Jon and I decided we want our land life to be as dynamic as our sea-life is. This is a messy time to be here and not everyone's cup of tea. But for us, it seemed like a move that even if we completely failed with, we wouldn't regret. 

So we did it. 

The move from hell

Or at least we tried to. We began filing paperwork before the hurricane, and put an offer on our house just two days after Irma. It's taken all this time to finalize our new life here and walk through the doors of our new home. 

For a lot of reasons -- hurricane outages, oddball personalities, sketchy bank lending practices, #islandlife -- every part of the process was difficult. While moving apartments about every two weeks for almost six months, we watched our paperwork get lost, our escrow fall through three times and everyone involved in our move and house purchase make money and make the process harder at the same time.

We thought we'd be able to move in by Thanksgiving, then Christmas, then never. It's a longer story for another post, but there was a day, Christmas eve to be exact, when we gave up. We packed up everything, made a list of everything we needed to do to fully exit Puerto Rico, and had a last teary drink to our dream of island life.

A few days before Christmas found us living in a cheap motel with everything we owned pulled from our leaky boat and stored in a rented minivan parked on the street outside. 

One of our friends sent us a text: "Step back and make sure this house is meant to be your and Jon's next move! I hope it is bc it is awesome having you in PR, but shit, you should not be going through this!"

And at that point, we absolutely weren't sure that all the decisions we were making were leading us anywhere.

Looking back, it sounds silly and melodramatic, but the hurricane tore all of our life plans apart and at the end of 2017, we felt emotionally adrift.

Then, just two days before New Year's day, everything suddenly fell into place.

It was so sudden that we still had no place to live when we went to sign our mortgage papers. We had to take Honey to the bank with us.

sail-me-om-dog-mortgage

I'm still shocked that it all came together. We are residents of Puerto Rico. We own a beautiful house in the Unesco World Heritage site of Old San Juan.

So what's the plan?

Our house is divided into two apartments that are exactly the same. Each have three bedrooms and a huge amount of living space. To say it's a change from our 200-square foot boat is a an understatement. 

It's a mansion, built by one of Puerto Rico's first rum barons, 200 years ago. And it has some pretty cool features, including its own 36,000-gallon rainwater cistern. As soon as we recover from the down payment of our purchase, we plan to install solar panels on the ample roof, to bring it completely off the grid. It's not the tiny home we planned on, but we still hope to pursue the alternative lifestyle we've come to love.

We'll be living in the top floor and hosting guests on adventures from around the world on the bottom. In the longer term, I hope to make our home a site for movies, events and retreats.

My secret, lifelong dream has always been to be the next Gertrude Stein -- to be the ultimate host and curator of interesting people. I've always wanted to bring together great thinkers, artists and people with Big Ideas, introducing them to each other, and gently prod forward great work in a place that inspires it. 

I know. That's a really lofty goal. More realistically, Jon has always wanted to invest in something that was more than just a home -- an investment and a place where he could practice the restoration skills we learned through #boatlife.

We both think we got the better end of the deal. (Here's a gallery from our Airbnb page.)

 

But, as I started off this post saying, it's terrifying. We've lived debt-free and relatively without responsibility for several years by living a tiny, off-the-grid life. Now we have a mortgage! And appliances! And a duty to others besides ourselves. 

Business-wise it's also a risky proposition. We'll be running our home as a business, while investing even more in our own businesses (his/mine) that we've run remotely for years. The slow economy here means that our work has to remain top-notch and that we continue to receive the amazing referrals that have kept us going so far. 

That's a big bet to take on ourselves and also that business in general will become increasingly global in the coming years. Luckily, we still strongly believe in both. 

In the long run we hope to restore Scally back into top form and use Puerto Rico as our home base while spending several months a year sailing the Caribbean and nearby shores. We're taking our time on that one, because we know that no matter what, sailing will be a huge part of our lives, so there's no need to rush to get back out on the water. 

What about the dog?

dog-old-san-juan

Yep, Honey definitely misses Scallywag. But the good news is our new home has some excellent sunny balconies that she's already staked out as her own. From little boat to cavernous mansion, she's the most adaptable animal we've ever met. 

 

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4 mindsets for boating en route to the Bahamas.

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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! 

 

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Why we won't be purchasing Captain In A Box.

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This weekend is the Annapolis Boat Show — perhaps the biggest yearly boating event on the East Coast. Essentially every boatbuilding company and boat product has a presence there, and Jon and I have been nerdily been looking forward to it for months, making a long list of boat-show discounted purchases we were ready to make in the next few days.

One of those purchases was Captain in a Box. I’ve been eyeing the online course, which certifies you as a professional captain, for more than two years. As a woman, I’ve noticed that the ratio of female captains to male captains that I’ve met is woefully low. I’ve also noticed that even though Jon and I are learning how to sail together, people often ask him if he’s working toward a captain’s license, and almost never ask me. The course has been on my gift wish list and a captain's license on my bucket list, for awhile now. 

So I was pretty excited to see Captain in a Box, also known as the Mariner’s Learning System, at the show. (Little did I know Jon was not — he had emailed the founder a while back with a few questions that were never answered, even though he was auto-subscribed to the company’s newsletter. Gross.) 

Anyway, the creator of the course, Bob Figular, gave us an admirable sell on the course and we were ready to throw down. But something was bothering me. 

First, he was only selling Jon. He didn’t look me in the eye, not once. He didn’t even acknowledge that I might be interested in the course too, until Jon asked about buying two courses at once. 

This is a cardinal sin of boating sales to us. We’ve passed on making huge purchases, like our sails, simply because the salesperson didn’t acknowledge me, one half of our boating unit, and half of our purchasing and decision making power, while making a hard sell. Apart from being personally insulting, my theory is that if you don’t see half the market in front of you, you’re not good at your job. And if your company doesn’t train or encourage you to see a woman as an equal purchaser and partner, they’re going to miss other things and deliver an inferior product. 

I’ve also noticed that, with this particular product, there were only guys — old white guys — on their coursework and marketing materials. In more updated imagery, there are one or two photos of women, but almost always accompanied by a man or in groups, or wearing copiously large life jackets like they can't handle themselves. Since Bob wasn’t trying at all to engage me, I began to flip through his brochures as he talked to my husband, and I noticed something even more concerning — there wasn’t a single photo of a person of color… anywhere. 

It sucks that he included visuals of women as almost solely in the role of “helpers”. But at least women were represented in his materials. I'll take it! However, there were only white women. Only white people. Not a single image of anyone of any other race, for a course that touts itself to be geared toward “recreational boaters, educational institutions and corporations and professional mariners.” 

This seriously pisses me off, because boating is, in many ways, on the precipice of dying if it doesn’t make itself available to a wider, younger, more diverse group of people. People don’t pursue things if they don’t feel welcome or see themselves reflected in it, period. 

And I don’t want to see boating, something I love, disappear. 

We can fix that by consciously opening up opportunities and marketing to a wider audience, outside of old white guys. By making recreation and careers with boats feel accessible and welcoming. By waking up to the fact that the narrow mindset of marketing to rich old white guys excludes a huge group of people, who have purchasing power and career investments to make. 

I understand the narrow marketing of multi-million dollar yachts. I don’t like it, but I understand that for a variety of entrenched socio-economic reasons, it’s likely that it’s going to be a white, CEO-level dudebro who can afford a very expensive boat.  

What I don’t understand is consciously limiting the audience and marketing of products, especially this product, that serves as a gateway to a lifelong love and income. Especially when your product is geographically independent and flexible. Your product can literally be used by anyone and could make the difference between locking in a new generation of boaters or not. 

So, as he wrapped up conversation with my husband, I piped up (he looked almost startled, like he forgot I was even standing there.) 

“May I make a suggestion for your marketing materials,” I said nicely. “Next time you make a run of these, you may want to consider including a more diverse group of people, especially people of color.” 

He became immediately defensive. “I have all kinds of people in my catalogues. Men, women, young old…”

I didn’t even point out the misogynistic way he pictured women in his materials and instead said, “Yes, but they’re all white.” 

“I’m a marketer, I'm going to market to my customer base,” he replied.

I began to explain that he literally makes his customer base by opening up boating as a viable career option for an affordable price. He interrupted (ugh) and said, “this is for people who have spent 300 or more hours on the water for a professional certification. There aren't people like that who need my product.” 

And this, my friends, is what’s currently wrong with the boating industry. 

I told him respectfully that he had lost us as customers and we walked away. He yelled a loud "FUCK" after us.

Despite two years of wanting this product, I will not, nor will I ever, support Bob Figular by purchasing it, and will be pursuing other coursework for obtaining my captain’s license. 

I hope that if you’re considering his product, you take a second thought before financially supporting his entrenched small-mindedness.

I also encourage you, if you’re at the boat show this weekend, to drop by and suggest he include more women and people of color in his marketing. If you’re a woman, make sure he meets your eye. Maybe if enough people speak up to vendors like him and others, we can see a stronger, more diverse boating community in the future. 

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8 Books and podcasts that will help you build your remote business

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It's taken me a long time to admit that I'm a read-about-it-first learner. I've always admired tactile learners, who learn by just jumping into things and figuring them out as they go. I, on the other hand, find that stressful and decidedly un-fun. When I want to learn something completely foreign to me, it comforts me to hear stories about how other people have done the thing I want to do. I'll read every book, article and listen to every story about the thing that interests me until I feel ready to make an educated move. Colleagues and friends often comment on how decisive I am to take action. In reality, I take quick action on new projects because I've secretly spent weeks or months researching the best way to move forward.  

Are you like me? If you are, I've pulled together the list of books, articles and podcasts that I used to teach myself how to logistically convert my skills into a business, manage finances and otherwise figure out how to pay for my adventuring.

What do you love that I'm missing here? I'm always looking for new things to dig into! 

Books

I'm fully aware that starting this list off with Tim Ferriss' classic is a cliche, and since I hate being a cliche, I waited YEARS to read this book. Don't be like me. If nothing else, swallow whole the message of working smarter, not harder, and start thining about ways to outsource your life. The mental calculus of how much time I was spending on small tasks that were keeping me from doing big things vs. paying someone else to do them for me was a game-changer and allowed me to build up my personal projects and business while maintaining a day job. 

Berkun's breakdown of his year working at the distributed tech company, Wordpress, is an excellent primer for remote work technologies and structures, especially if you already or want to work closely with other team members. His breakdown of holocratic work structures and rules for asynchronous work management are thought provoking and worth a read, even if you're an IRL manager. This book is best for people who have to keep working and managing people on the road, but definitely a peek in to the future of work for anyone who's curious. 

Part memoir, part Pixar business manual, I found this book an essential guide to building a business where employees have autonomy and a sense of self-fulfillment that will allow bosses to step back and be more hands off. 

Podcasts

There's a podcast for literally every interest. I find podcasts about business-building, marketing and detailed descriptions of how people financially have made big things happen totally engrossing. I am, however, allergic to the sound of loud bros and gushing women, who oddly make up a large contingent of this kind of podcast. There isn't much middle ground between "get off your ass" and "reach your dreams!" so what you listen to comes down to your personal tolerance for those kinds of diatribes. 

Pat Flynn's Smart Passive Income

Ultimately, the goal of working while traveling is always in some part to increase passive income, so that you can spend more time doing what you want... even if that's working on something else. Pat Flynn has a weird, nichy empire built on the topic, and I found his podcasts to be interesting, well-edited and without the hyperbolic broeyness of many of his counterparts. He has a blog as well, but I preferred to listen to his interviews with business owners. Start with his three-part intro series and then go from there -- the people he interviews all basically have taken his advice and adapted it to the things that they're good at. I love the frank money discussions here, which really break down where to spend your time per dollar.  

Sail Loot

Specific to sailing in content, but helpful for working while adventuring in general, Sail Loot interviews cruisers on the gory financial details of what it took to ship off with cash in the bank. Part financial podcast, part gossip fest with bloggers whom many cruisers may recognize, the podcast is useful in the way that it shows a hugely wide variety of ways people have gotten to their lives aboard. For some people it took a year, for others it took 20. I give a lot of credit to podcast host, Teddy, who's trying to set sail himself, and thusly asks crazy specific financial questions of all his guests. 

The Sailing Podcast

Not a financial blog, per se, The Sailing Podcast is basically an open space for hosts David and Carina to have long, winding conversation with people who have sailed the world. By default, those conversations often devolve into "but how can you afford it" territory. It's a fun listen for the wild yarns. 

Keep Your Daydream

In this sometimes winding podcast, adventurers of all kinds are interviewed about their crazy life stories leaving behind 9-5 jobs and how they were able to afford doing so. I appreciate the broad array of guests but take note that the podcast tends to be heavy on the inspirational takeaways. 

Startup

Perhaps the most well-known of the trying-to-make-it podcast set, Startup chronicles a journalist's effort to break into the startup tech industry. While not directly applicable to funding a way to escape, it's a solid introduction into the startup universe if you've never worked in it. 

 

Interested in reading more? While it's not about money or business per se, I also found that a book on decluttering helped me rearrange my financial goals.

You can also read the first and second part in this series about working remotely:

 

How to build a remote team that won't trip your business up.

Last week I published a beginner's guide to working while cruising, detailing how I structure my  days as a remote business owner. One unsurprising piece of feedback I got was that many people have tried to hire remote workers or people who travel while working, and have found them to be less reliable than traditional workers.

If this rings true to you, I feel your pain.

I've run several remote businesses and between them I've culled through thousands of cold applications for remote positions. It took lots of trial and error to pick the right people to work in a distributed or remote environment. It also takes a lot of work to be a good manager to remote employees. With that said, here are my major guiding principles for building a remote team of people who travel. 

Hire remotely (or in other time zones) only for jobs that can be done asynchronously. 

The nitty gritty of this depends on your industry, but I've found in editorial that short turnaround work like breaking news, social media for breaking news and coordinating with teams that need to work together closely on tight deadlines (sales pitches) needed to stay on a US timezone to work well. However, remote workers can be a boon if you need to expand your workday reach. I've seen great success in hiring people from Europe to break stories earlier than East Coasters would be able to. 

Build a job application that tests responsiveness as part of the interview process. 

I've hired roughly 100 people in the last 5 years and for the last few positions the ratio was about 2000 applicants to every open position. Eek!

I had to remake how I hired and it's now super effective.

First, determine the four to five qualities you need in the position and then develop 2 levels of application questions.

The first level should be for ability to handle details and responsiveness -- my favorite tricks are to ask them to deliver their application back by a certain time, add a specific word in their cover letter and to have them send something in PDF format. That rules out about 80 percent of applicants and you can auto-search those responses in applications (Protip: in greenhouse.io you can bulk search applications.)

Essentially, you shouldn't have to look at your fist round applications to weed out the worst of the bunch. Use the second round app to ask questions and give challenges that illuminate their skill set.

Read those applications and take notes on where they're weak, then use your actual interview only to clarify what you've already learned and drill down on weaknesses. I find in those interviews that asking them questions about real experiences rather than hypothetical situations gives you a better idea of what kind of person they are. For example, "tell me about a time you made a mistake and how you fixed it" can really tell you a lot about a person. 

This application process can work for any kind of employee, but it's especially important for remote workers, who need to be extra detail-oriented, resourceful and tech-savvy, as well as responsive. 

In your interviews, ask for details of travel and routine.

People who are good at this aren't good by chance. They, like me, have really strong plans around getting internet, building structure into their days, and they think A LOT about how to do their jobs well. I think it's totally fair to ask that stuff as part of the interview process. I can talk all day about our wifi and cell boosting rigs! If they're new travelers, I'm more likely to pass on hiring because they haven't figured their you-know-what out yet.

Never hire someone for their first job as a remote worker.

They haven't been broken in yet into work norms in general. I totally believe in giving people first chances, but new workers need to be socialized before they're set free! (And sorry, someone else can do that.)

The more senior the position, the better a full-time traveler will work for you.

The longer someone has done this and the more they know about their area of expertise, the more likely they are to be able to handle both at the same time.

When you're working with new people, give them a really clear set of guidelines for cultural norms and behavior for remote work. 

Go over a one-sheet on your employee's first day with a clear set of consequences for what happens if they break these norms. This sounds like kindergarten, but it actually is quite relieving to remote workers to have guidelines to follow and they usually follow them well. Remember that they're in their own kind of vacuum from your business, and following rules allows them to have a stronger sense of job security.

Never let people *start* traveling at the same time they start working for you. 

I had a two-month ban on traveling for new workers at the last couple of roles I ran, and it worked really well for those people wanted to use their remote work to travel. This harkens back to the advice I gave on my last post, which is to give yourself time to figure out your travel and build a business. The people who work for you should do the same.

Traveling while working means slow travel.

Some may quibble with this, but in my experience, you need to build in lots of time for working and if you don't, you'll always run into problems. If people have ambitious travel plans while working, I get a little suspicious and ask for more details. 

Let your like recognize like.

There's a certain vibe that really good remote-working travelers exude and I can smell it for miles (insert dirty backpacker joke here.) You probably know what I'm talking about, and don't ignore it! 

It takes years and commitment to get a good groove and a lot of people, often really excellent workers in in-office environments, never get there. Remote business management and working isn't for everyone, but for the people it works for, you can expect more loyal employees, a stronger work ethic and often a discounted cost of work. Providing your employees and contractors freedom in exchange for them earning your trust is a foundation of building a great business, and remote working can truly accelerate that. 

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

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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.