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! 

 

How to live on a boat in New York.

Despite the fact that we’re now cruising full-time, I probably get 5-6 emails a week from people who want to learn more about living on a boat, especially in New York City. Since being covered in Forbes, I've gotten a boatload (pun intended) of people asking the same questions, so I figured a blog post was in order! 

There’s a good reason that not that much information is publicly available about this topic: living on a boat in the New York area as your full-time, permanent residence is, as far as I've been able to tell, technically illegal at every marina... so, intrepid aspirational liveaboards, read along at your own risk. 

However, if you have even an inkling that you'd like living on a boat, in NYC or otherwise, you definitely should try it! There are very few of us who actually get it together to do it, and no one I know has ever regretted it. 

With that said, come with me and I’ll drop some knowledge on ya about how to do it. 

Don't live on a boat to save money.

Every boat is different and living on a boat can be an extremely economical way to live in an expensive city. But don’t discount the costs associated with purchasing and maintaining a boat. Every repair you make will cost you thousands instead of hundreds of dollars. That’s why $1000 is affectionately referred to as a “boat buck.” So, consider that whatever you save in rent will likely go back into boat maintenance in the long run. There are tons of blogs that outline their monthly or yearly costs of living and cruising on boats.  Mark Nicholas' classic on being a liveaboard also outlines the general costs of living on your boat. 

Look for marinas with discretion. 

No marina in the NYC area will say they accept liveaboards. Look instead for marinas with "wet winter storage" or in-water storage, and for marinas who accept "frequent stayaboards". 

Many marinas accept stayaboards, but you need a separate permanent address (P.O. box is fine) for legal and tax purposes, and in emergency situations, another place to go. You don’t have the same rights as a renter in an apartment. Your slip doesn’t count as your home. 

In short, it's accepted by many marinas to stay full-time but not quite legal, though many people have done it for years and years. 

 This can be an inconvenience at times -- if they have to fix the water or facilities they work under the assumption every tenant doesn't live there full time, even if they know they do, so you have to make alternative plans. This wasn’t an issue for us but it's different at every marina. 

There are a number of marinas in the same canal, so it's up to you to choose cost and amenities over convenience

You'll have to call around to see about current policies. Lots of people live part or full-time in marinas around New York, but you have to be discreet and respect the rules of the marina hosting you. We've been called out for NOT being discreet, by even noting that we've lived on a boat in NYC, without ever disclosing location. (Hey you, aspiring La Vagabonders, don't even consider starting a YouTube channel if you want to live aboard in NYC.)  

Liveaboard slips are very marina-by-marina. Some people care a lot, and some people don't care at all if you stay all year. Look for places that provide bubblers (sort of like giant versions of the kinds find in aquariums) so that the water around your boat doesn't get iced over. 

As far as more general information, I'd really recommend Mark Nicholas' classic on being a liveaboard as well as Facebook groups on the subject. Sailing and Cruising has a lot of info on living aboard and there are about 5 million blogs on living aboard -- the easiest way to start getting to know all of them is to start liking them on facebook (try ours  -- Sail Me Om and Sailing Chance, who is also in New York) and you'll get suggested more. 

Water.

Remember that when you live on a boat you aren't connected to a water or sewage system.

In summer, water is a no-brainer, just fill up your tank every so often from a hose right at your slip. In the winter, water is annoying but doable. You'll get an extra long hose, or some docks link their hoses together and they fill directly from pumps on land. This is annoying. Sometimes people will leave water in the hose and it'll freeze and you have to do ridiculous things to unfreeze it (like taking 200 feet of hose into the shower to melt it, true story) but totally doable. If you have large water tanks it's a non-issue (we don't, and it was still only an every-two-week affair for us.)

Pumpouts.

In every marina we looked at, they didn’t have pumpout services for heads in the winter (as in, pumps to clear your toilet tanks). Your alternatives for this include: don't use your head at all, or only do #1 and open it straight into the river. Use marina bathrooms for everything else. You can also get a composting head (toilet), which renders this a nonissue. Note that especially in winter, you shouldn't plan on showering on your boat because of the moisture, so you'll be in those bathrooms regularly. Also, most FT boaters keep pee-only heads anyway, because it dramatically reduces smells on your boat. There's the gross explainer on that. 

Know your boats and their capabilities. 

Or at least what kind of boat you hope to live on. Powerboats provide a lot more space but tend to be more expensive to travel on than sailboats. Sailboats tend to have less space, but after the '70s era-runs, they become much roomier inside.

Note that houseboats are neither sailboats nor powerboats. They are meant to be in one space and not move. Just because you live on your boat, this doesn't mean your boat is your houseboat. In any case, basically every boat is expected to have a working engine, and you're expected to have insurance to keep it in almost any marina. Your insurance rates may vary wildly depending on the condition of your boat. Also, don't expect it to be okay for you to tow a derelict boat into a marina to live on. It won't be accepted. 

What size boat can you live on?

There's no rule for this, but we've found that the smaller the better. 37 feet is enough for us two, even though we thought that would be too small when we started. Many people make the mistake of buying big and regret the dock fees (charged by foot) and maintenance fees (which get infinitely more expensive as you go bigger). So if you're not sure, try out a friend's boat for a couple of days or Airbnb a boat of the size you're looking for to see if it's right for you. 

That's it! What other questions you got? I'm happy to answer them. 

A brief soliloquy on being constantly afraid while sailing 1500 miles.

Yesterday, we left New York City to start Part II: Sail South in our two-part, very simple sailing journey. The return to the city marks about 1500 miles of sailing.

That is shocking to me. We've come a long way from not knowing how to sail at all just three years ago. While catching up with friends and old colleagues in the city, Jon and I were asked over and over again, “aren’t you ever scared?” Jon’s response is always, “nah!” and mine is “yes, constantly.” 

I can't believe we've actually made it this far. 

I was brought back to a blog I wrote a couple of months ago but never published, mainly because I was a little embarrassed. Fear isn’t something we like to talk about unless we have a way of conquering it. Lots of adventurers and writers have amazing prose about how they conquered a fear, how they’ve moved beyond it to live their best life. This blog post isn’t about that. It’s simply an acknowledgment that for me, fear is a constant, that it’s exhausting, but it doesn’t stop me from doing things I love to do.

I think there are a lot of us out there that don’t talk about that, so I wanted to do so for a minute. I’m including below my original blog post, and a bit of an epilogue of what I’ve learned about fear since writing it.


Last night was the first time in a month that I’ve driven the dinghy. I’ve refused to pilot it since the Great Dinghy Flipping Incident of 2016, which for the record, I still don’t find funny. While our outboard has long since been resuscitated, I’ve been embarrassed and ashamed about letting Jon take the wheel — in part because it compromises my own independence and in part because I just don’t believe that there should be anything that stops me from doing things as well or equally often as Jon. But I’ve also been filled with crippling dread about being responsible for myself and other people (and Honey) inside that dinghy. 

Nevertheless, Jon forced me to get back in the Hypalon saddle, and drive the damn thing to shore to take the dog out for her last walk of the day. Enough time had passed, the motor was working just fine and he was done chauffeuring me around.

So I did it. Nothing of note happened, and I’ve driven it several times since then. Fine. That’s how we get over fears, right? By just doing the thing? But that’s not really the point of this post.

I want to talk about fear. We fairly universally can relate to acute fear, like my little story above. Something scary happens and it’s natural to be afraid of it again. But some people (me) are just naturally more afraid than others (Jon). 

I’ve done a lot of ostensibly brave things, both with Jon and without — I’ve traveled and lived alone in developing countries, I’ve worked in war zones, I’ve managed big teams of people, had to fire lots of people, spoken to large crowds and done a few nominally dangerous outdoorsy things with questionable equipment and guidance that I probably should have said no to. 

I’m also somewhat prepared for legitimately scary things. The few times I’ve been in actual danger, I’ve been calm, calculated and have extricated myself quickly and efficiently. I’m well trained in self-defense, and at my peak performance could disarm attackers of their weapons and take down two people at a time. Like I mentioned in my last post, I like to I learn literally everything I can about new things so that I can be well-prepared for any issues that come up. I’m all up in the grill of preparedness and taking smart chances on things. 

Despite that, I’m scared all the time. Of basically everything. I don’t mean gut-wrenchingly, panic-attack scared, just low-grade, constant worry that something will go wrong scared.

Is it my half-catholic, half-jewish heritage? Am I genetically bred to worry? Perhaps.

Here is an abbreviated list of the things I’ve worried about in the last 24 hours:

  • Driving the dinghy
  • Driving the dinghy at night
  • Hitting a mooring because it’s dark
  • Black mold
  • Falling in the water
  • dropping my phone in the water
  • Honey falling in the water
  • Jon falling in the water
  • Dying of skin cancer
  • Running aground
  • Not having reception for work calls
  • Losing clients because I don’t have enough internet
  • Losing business because I think my voicemail/voice sounds like I’m 12. 
  • Losing business because I don’t wear enough makeup on video calls
  • Going into bankruptcy and not being able to pay off my student loans because of all of the above problems
  • Getting raped, stabbed or abducted as I walk the dog
  • Falling over and getting a concussion while walking the dog alone and not being able to call for help
  • Losing my personality from the concussion
  • Blowing up the boat by using our propane-powered water heater
  • Not calling my mom enough so that she’ll think I don’t love her
  • Not calling my friends enough so that they’ll think I don’t love them
  • Not telling the people I love that I love them before I die. 
  • Dying alone
  • The weird bumps in the wood that are appearing in our cabin walls.
  • That our rigging will spontaneously pop apart and the mast will fall on me
  • Being too old to have children by the time I want them
  • Botulism 
  • Getting food poisoning because I’m not sure if our fridge/freezer is cold enough
  • Wasting food because we might not have time to cook it before it goes bad
  • Thunderstorms.

In contrast, I asked Jon whether he was scared in the last 24 hours, like for example when taking Honey to shore late at night. After some thought he said, “maybe if a car drove by really slowly and flickered their lights at me in a creepy way. Then I’d be a little scared.” 

Perhaps it’s the long hours of staring out into the horizon and being alone with my thoughts, but I’ve started thinking about fear and anxiety really deeply for the first time and I’ve only just started realizing that not everyone has to make a massive effort every day to conquer their fears of the unknown. Some people, like Jon, just do the thing

Hopefully a few of you are as flabbergasted as I am that there are people in this world are able to get through a complete any day or activity, without the million thoughts and fears that go through their heads while doing it. I mean, what would you do with that extra time? I would have written an entire compendium of novels by now with that brain space. 

It’s also a shock to me how some people react to scary situations. In contrast to my ultra, almost paralyzing calm in the face of fear, I’ve noticed that Jon will treat a scary situation like a joke of the first order. Once, when taking a wrong turn in Hebron while working in the West Bank, we found ourselves surrounded by some very angry Israeli military with AK47s. I froze and gripped the sides of the car, urging Jon to back the car slowly away as they ordered. He, on the other hand, started laughing and joking with the soldiers. 

Then there are those people who seek out fear. I can’t even, with those people. According to a frustrating article about people who apparently aren’t terrified all the time so want to seek that feeling out, from The Atlantic, “to really enjoy a scary situation, we have to know we’re in a safe environment. Lots of people also enjoy scary situations because it leaves them with a sense of confidence after it’s over.” 

That makes intellectual sense to me but there must be a fundamental difference in brain chemistry between these people and me. The older I get, the more unsafe the world seems. This plays directly into the writer, Allegra Ringo’s, additional assertion that “things that violate the laws of nature terrify us.” (which, unrelated, pretty much sums up my fear of mimes.)

The more I know what’s possible — rogue waves, freak storms, electrocution by water — the more susceptible to fear I become. Perhaps the sea is where the laws of nature are most able to take their free reign. But as a city girl whose greatest metaphysical mystery prior to living aboard was where New York’s constant hot trash smell came from, the ocean is a scary place.

I have a deep, wild fear of the unknown, starting with a complete lack of understanding of the range and moods of the the substance on which I float. 

This is different from being scared of the water, which I am not — and which Jon is. In fact, that’s the only fear he has that I’ve been able to discern of his — the dark mysteries of deep water hold about as much power over him as the entire rest of the world does to me. So, I go about my business as if everything doesn’t scare me, and Jon lives on the thing that scares him the most. We’re a fine pair. 


After discussing my constant fear with a few different people since writing this post, I haven’t found any solutions, but I’ll put forth some hypotheses for cures in case any of them resonate with you. 

1) Do something that scares you every day. I’m pretty sure this oft-repeated mantra was handcrafted by a Silicon Valley bro whose version of scary is an indoor skydiving cocktail hour or maybe covering a bar tab for a bunch of friends when he wasn't sure what was left in his bank account. Sure, I can say I live by this mantra, if only because literally everything scares me. Last night I opened and cooked with a dented can of peeled tomatoes (See fear of botulism, above). I played with fire and didn’t get burned. Check and check with that one. I don't think it helps.

2) Get to know your equipment, have trust in yourself and your experience. The overwhelming response of women in the sailing community that I showed my fear to fell into some version of this tactic, which is probably the most practical of any that I’ve seen.

I see two downsides to this — if you don’t have a lot of experience with a new thing, you definitely shouldn’t trust yourself or your equipment because you don’t know where your limits are. I’m sure after a few more thousand miles under our belt, this will feel like a no-brainer, but after our first thousand miles, I’m still not convinced. Every outing is a new chance for something completely insane to happen. In the meantime, I keep a close eye on our inclinometer and let the main way out every time we pass 25 degrees of heel. 

3) Know the difference between fear and anxiety. After reading a really wonderful series of blog posts by a fellow sailor and therapist, I know that what I feel is actually anxiety. Not panic-attack level, medication-necessary anxiety, just run-of-the-mill Jewish Grandma worry. Understanding more about how my brain works has been helpful. It hasn’t cured me… but perhaps reading up on how you feel can make a difference. By understanding what’s happening in your brain chemistry, you can let feelings pass through you and acknowledge them, and ultimately let them go in a moment of zen, or treat them professionally if necessary. 

4) Say yes. Funnily enough, as I was first writing this blog on fear, blogger Carolyn Shearlock of The Boat Galley, published her take on fear. It’s an indirect treatment for sure, but one I’ve always subscribed to. My version of “say yes” is “try everything once.” Whenever I’m afraid, I tell myself, "I can NOT do that thing ever again, if I know I don’t enjoy it, but I’ll never know until I try it." Like Carolyn, I rarely say no to things, despite how I feel on the inside. That doesn’t make a difference, however, in how I ultimately worry about doing those things. 

5) Fake it ’til you make it. Or, my personal philosophy. Despite never not being afraid, I continue to believe that if I do something enough, I’ll someday be fine with it. If not, at least I’m still doing it, which is better than doing nothing at all. 

In fact, while literally writing this post, I employed strategy #5 to great effect. I had to take a break to take the dog to shore for her walk. I was alone on the boat for a couple of days, reluctantly practicing my rediscovered dinghy management skills as the sun splayed its most gorgeous sunset-colors across the sky. I pulled up to the dock to a crying toddler. 

His mom was trying to comfort him as he wailed, “I don’t want to go on the boat! I’m scared of the boat!” In that moment, after spending an hour trying to capture all my anxiety about sailing in one blog post, that child was my spirit animal. 

“Look!” His mom said brightly. “This lady and her dog are coming from a boat!”

His mom looked desperately at me as I caught the edge of the dock and began to tie the dinghy off. “You guys are having lots of fun on the boat, right? Isn’t it a beautiful night to be on a boat?” 

I looked that little kid right in the eye and said, “Totally. It’s super fun and gorgeous out there. You’re gonna love it!” 

The mom lifted her sniffling, not quite convinced child into their dinghy and sped away. I watched them with mixed feelings. Did I lie? Not quite. I love our boat, and the ocean, and all that comes with it. But did I absolutely feel for that kid and completely identify with his explosive tears? Absolutely. 

This is an actual photo I had the presence of mind to snap of the sobbing toddler being whisked to his boat in the sunset. I definitely wasn't lying about how gorgeous it was.

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

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. 

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

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. 

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. 

 

A couple's guide to living aboard a boat in winter.

So many of you have asked about what it's been like for us, and our marriage, to move aboard a boat in the middle of winter.

We've been toying with ways to show it to you best, and luckily our friend David Freid dropped in after a particularly big snowstorm to film a short doc about what it's been like for us. 

Freid is an old friend who, in a former life, traveled the world with us when Jon and I ran a nonprofit in conflict zones together. (THAT was good training for living on a boat, to be sure.) He's seen us at our best and our worst, so we were delighted to have him barge in on our tiny space.

A few of behind-the-scenes extra features: Jon MAY have actually been still drunk or hungover while filming those outdoor shots... The term drunken sailor doesn't come from nowhere. Also, I have so few clothes on the boat that I realized I had accidentally ran out of clean pants the day of filming.

I had to make an emergency ferry run to the mall across the river. I called Freid in a panic as he was driving over, yelling "Stall the crew, I have no pants!" That will probably make it into the bloopers at a later time. #boatlife.

By the way, all the work that Freid does for MEL is gorgeous. I've been jealously watching him globe trotting for the last six months shooting things, and they're delicious to watch.

Last time he stayed on the boat, he slept in the captain's berth and had dreams he'd been buried alive in a coffin, so maybe if we offer him a spot in the main cabin with a double bed-sized berth, he'll come back and film again in the summer when the boat (and our coupledom) looks a little more enviable. 

And hooray! Our story has already been featured on Tiny House Blog, one of my favorite small living publications. It was so fun to stumble across my husband's face while surfing the interwebs.