Spirit Quest

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

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.


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?


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. 


The world is as kind as you make it: a daily practice.

Greetings from Puerto Rico! Our little boat has made it a few hundred miles since I last checked in, slowly working and sailing our way through the Bahamas, across Turks and Caicos, bashing along the Dominican Republic, and finally landing at south coast port of Salinas.

It's time for a land break while we wait out hurricane season, which has given me a chance to reflect on how this weird watery life has changed me since we left New York a few thousand miles and more than a year ago.

One thing has become clear: Traveling through the islands has made me a kinder person. That's making life, wherever I go, infinitely better. 

As I took a break from the Caribbean to visit favorite cities and friends, I noticed everyone, especially strangers, were more open to me. They were friendlier, ready for conversation, to lend a hand.

In my first few days back in the States, I was confused.

People were saying hello in the street, striking up conversations with me in lines, helping me fix and unload and arrange things... those nice things you do for people where everyone knows each other. They were offering kind smiles and human acknowledgement. 

This wasn't unusual per se -- we have passed the last seven months living in a chain of islands where this is the norm. Where everyone stops to help someone else, because you know the smallest acts can make a huge difference to someone's livelihood, safety or ability to withstand the elements. Where everyone is kind to each other because you know you'll see them again.

Except, I was in Baltimore and LA. These are places I know well, where I have spent lots of time without anyone saying hello meeting me in the eye. What was going on? My big city suspicions were raised. Why were all these strangers being so nice to me? Why was this thing or that thing being offered? What was the catch?

Then it dawned on me: The world hasn't become kinder, but I have. And when I approach the world with openness and warmth, the world returns it joyfully. 


It's not you, It's me

Stay with me here, while I get a little woo woo on you. You can't travel to as many odd places as I have without being willing to befriend strangers and roll with weird invitations and situations. 

But in terms of kindness, I've undergone my own evolution.

As a student, I learned to harden myself so that I wasn't taken advantage of.

As a woman, I learned to never hold anyone's gaze or participate in conversation long enough to encourage any undesired actions.

As a New Yorker, I learned that my best friends were my resting bitch face and a pair of headphones. 

That's not to say that I haven't been a practitioner of kindness. I've been a longtime believer in Radical Empathy, and my belief in empathy and conflict resolution has driven me to great lengths in my professional career -- to build a nonprofit that taught storytelling in conflict zones. To help grow a media startup that builds empathy through viral storytelling. To seek out 10 years of work that benefits social good.

But I've been pretty bad at practicing it in my everyday life. 

Until this last couple of years, my main approach to the world has been, with reason, one of self-defense and skepticism. I'd like to say I've always practiced kindness, but almost exclusively to the people I already know or toward causes I've felt passionate about. That left my circle of friends small and tight, and my daily interactions almost exclusively transactional.

Somehow, more than a year of cruising through small towns and seven months of living in the islands has worn down my defenses like waves on sea glass. And I'll be the first to admit that the softer-edged me is way better. 


Someone else won't do it

One of the biggest lessons I learned from traveling to remote locations is to reprogram my brain from the default big-city idea that there's always a "someone else". When you're on an island in the middle of the ocean, exposed to elements and limited resources, there are few "official" modes of help, in emergencies or otherwise. You can look around you, on land or in an anchorage and realize, this is it. These four or five boats, or this town of 500 people is all we've got to solve a problem. There is no one else. So every person who looked stuck, struggling or asked for help was suddenly my problem. No person left behind. 

That seems like a hassle, but it's actually a lovely way to approach the world. You can address any situation with the certainty that you're there exactly at there right time to help someone else. And they're there to help you.

My change in my own attitude became clear to me back in Georgetown, in the Bahamas. While hiking with some cruising friends and some other folks visiting from New York, we came across an older fellow who was clearly struggling in the heat. We asked if he was okay. He waved us off and told us he was just taking a rest.

Our New York friends continued on, satisfied that he could take care of himself. The rest of us stayed put, gave him some food and water, slowly walked him back to his dinghy, and made sure he got back to his own boat all right, where his wife was waiting for him. 

We talked about it later -- this wasn't a classic case of Bystander Effect and the New Yorkers weren't wrong in their actions, per se. He had said he was fine.  But we knew that there might not be another person coming by the rock on which he was sitting. That no EMT could be quickly called if things escalated. All that guy had was us, who happened to come across him at just the right time. 

When you know there's no one else, you have no choice but to start watching out for each other.

I've also found that moments like these always come back around.

When we returned to Luperon in the Dominican Republic late one night from a trip to the States, our pre-arranged dinghy ride to our boat was nowhere to be found. We stood on the dock with our bags, our dog and the fatigue of 12 hours of travel. It was midnight, in a tiny seaside town that spoke exclusively Spanish, and it looked like the only way to get to our boat was going to be to swim. We asked around at a few bars that were still open, but no one had a boat. So as a last-ditch effort, we borrowed a VHF radio and called, 

"General announcement to the harbor: Is anyone still awake and willing to swing by the dock to take us to our boat?" 

A woman immediately hopped on the radio and, without knowing who we were or any details, said she'd be out in five minutes to pick us up. And just like that, we were home.

I have stopped asking myself: Is there anyone else coming that would be better equipped to deal with this?

Instead I step forward with good intentions and the best I can do, and hope that other people around me will follow. They almost always do. 


Make time for kindness 

These moments of kindness aren't always ones of trauma or emergency. Most of the time, practicing kindness is being generous with your time: taking an extra five minutes to lean into a conversation instead of shut it down, to compliment people and get to know them a bit better, or to offer or listen to some advice. 

Part of adjusting to a tropical clime is learning to slow down. And in that slowness, you finally have room for those little niceties that make the world so much more pleasant.

That's hard to do while working, where people don't understand that even if you're not in an office that doesn't mean you don't have a full workday. I've put it upon myself to schedule in that time.

I no longer schedule back to back calls if I'm in a new public place, as I'll need to have time to get to know the people who run the restaurant, bar or coffee shop I'm in.

I leave an extra five to 10 minutes to get anywhere, as I know I'll probably get roped into some kind of conversation along the way. 

I can't schedule my days with the precision I had in New York or LA, but getting through the day is so much easier and more fun, knowing that I can spare the time to get to know everyone around me and explore the places that I'm in. 


The more you give, the more you get

By opening myself up to help and leaving more space in my day for kindness, I've also found that I've become less suspicious around new people.

I haven't lost my skepticism toward other people's intentions but I have forced myself to stop assuming that strangers are a threat. Men aren't always there to catcall me, vendors aren't always there to hustle me.

This manifests in my attitude in small ways: I make eye contact with everyone I meet, and I greet them with a hello and a smile if they choose to make eye contact back. If you're from a small town, you're probably rolling your eyes right now, and I get it. But for those of us who have spent most of our lives in big cities, eye contact with strangers is a radical move! 

I've lost my automatic "no to the universe" vibe, and in return, I think my good intentions come back around more often. I think my openness shows on my face and from it, I've been party to a million small interactions that have made my days more fulfilling.

I'll never be good at improv, but I like to think of my attitude as shifting toward a "yes, and" mentality that allows me the space to better understand the people around me and my place in the world.


Karma is a boomerang

Traveling basically full-time means that I can't get deeply involved in one community, but I can make myself available for a thousand small interactions that can make a difference to someone else. I also try to participate as much as possible in online groups for people asking for help and advice, trying always to give more than I get. 

That phrase, "Karma is a boomerang" is one of my favorite phrases. As a teenager, I wrote it on a post-it and stuck it to a mirror in my bedroom. I used to love it because I knew that anyone who did me wrong would have their negativity served back to them, with sprinkles on top one day. I took great delight in imagining the cosmic revenge of the bullies and mean girls of my earlier years and how much better off I'd be. I brought a lot of that attitude into my adult life, with the underlying intention of "not being mean, rude or awful" instead of actively and intentionally practicing kindness.

But as I've gotten older, I've come to think about karma far less in terms of retribution, and instead in terms of all the good energy I can put out into the universe and the myriad ways I can do it.

It's not always easy. But even objectively, the time and effort is worth it. Studies have shown that people acting generously toward others find more happiness in their own lives than those acting in their own self interest

Generosity can take a lot of different forms, and I've really enjoyed exploring what generosity means to me, especially in the time and love I reserve for others. 


“We make a living by what we get. We make a life by what we give.”

- Winston Churchill




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.

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. 


How traveling solo helped this woman find love and a beautiful guesthouse business in Peru.

As part of an ongoing series, Sail Me Om presents the stories and practical advice of people who have made daring life choices about how they live and work. If you know of an adventurer whose story should be told, tell us about them.  

Megan Youngmee is a talented graphic designer who worked full-time and freelance for more than 150 startups and Fortune 500s in Los Angeles. Three years ago, she ended a 2.5 year relationship, sold her furniture, cashed in her retirement fund and left on a trip of a lifetime. Eventually, Megan landed -- married, a mom to one and a guesthouse proprietor -- in the Sacred Valley in Peru. 

This is Megan's story, in her own words. 

The spirit quest

For quite a few years I had felt unsettled. The further I moved into my career, the more I realized the job, titles and money weren't actually going to make me happy. Finally, at 29, I decided to do a bit of travel and soul searching because after having everything I thought I wanted and worked for, I had never felt more disconnected, stressed and empty. 


The spirit quest started with a cross-country road trip with just my dog, some clothes and my computer. I connected with friends across the country and spent a month in my home state of Pennsylvania. On the very first night back in my hometown, I reconnected with my middle school crush, after 18 years apart. It was the beginning of my trip, but by its end, Eric would be my husband and the father of our 4-month-old. 

I spent that time at home reconnecting with him, friends and family, and planning a six-month international sabbatical. I looked at this trip as a time to ask myself who I was and what I wanted, discover the meaning of home and connect with my roots. The trip led me to Peru, Bolivia, Brazil, and the UK. It took me finally to South Korea, where I was born and hadn't been back in the 28 years since my adoption. 

Overall, I spent one year traveling internationally and all over the country. 

I spent a month in Beopjusa Temple in the Songnisan mountains, chanting with monks under the stars, and connecting with my roots. There were so many strong Korean women who felt like adoptive mothers. They taught me about Buddhism, motherhood, gentleness, self-love and the history and culture of my land. 

I saw the mountain ranges of Huaraz, Salar de Uyuni in Bolivia, Foz de Iguaçu, Brazil and the epic landscapes and ruins of Peru. 

I was alone for all but three weeks, which was a great time to reflect, spend time in meditation, and really ask myself what I wanted every day.  

During the trip I had never felt so alive and healthy. I also was doing freelance work on the road and realized that I could make money anywhere and be home anywhere. I was writing business plans, doing design, writing, learning the ukelele and spending lots of time in nature.  Plant medicine ceremonies also were part of giving me a clearer sense of who I was and where I wanted to be. 

The decision to move to Peru

The final decision to really make this lifestyle a reality happened when I returned to The States. I had left my life for a year and came back to a few amazing job offers.

Eric proposed, and he, like me, felt that his life was in transition.

Then, he asked me, point blank, "What do you really want?" 


I had spent the majority of my travels in Peru where I had fallen in love with people, language, delicious organic food, fresh air and glacier drinking water. 

"Honestly, I keep thinking about Peru,” I told him.

He said simply, “let's get our tickets.” 

I had secretly hoped he'd say that. But I was also terrified he hadn’t urged me to take the jobs and money in NYC or LA. 

We decided that we would take a chance and try traveling for two years. If we didn’t find something stable in that time, we could always move back and jump back into the grind. 

We found an insanely cheap one-way ticket and in one week we had a job offer to work at a hostel in Peru. The tourist season was coming and we built our wedding around our life plans. We planned our wedding and got married in three weeks, and then, just one week later, we found ourselves in Peru. 

In hindsight, I think that if we overthought the decision, we might never have never made the move. Something about stepping out into the abyss with a partner and doing it without too much rumination over the "what ifs" made the decision easier. 

Into the inn business

First, we started in Cusco, working at a hostel. When I was traveling, I noticed there weren't many places that didn't cater to just gap-year kids or folks in their golden retirement years. There was a huge price and age divide.  

We had friends in the Sacred Valley who were renting a house in the hopes of making it an inn and it just wasn’t working. Eric and I somehow both had a sense that we were home when we were there. We visited every couple months, and then found out they were about to leave the house and the business. We saw an opportunity.

We moved in to see how it felt to live with lots of people. And we needed to get an idea of how much work we'd have to put into the property to be able to start filling rooms. 

After a couple months, we signed a lease and started doing major construction on the house. We tore up old carpet, refinished the hardwood floors, upgraded the plumbing, changed out lighting fixtures, we spackled, rebuilt broken walls and painted.

When creating this place, we wanted to make something that was homey — a place that had the benefits of community but was quiet and off the main tourist path. It has an open vibe that a traveler can make of what they want — some hike, while others explore the local culture. Some take time to learn the language, many people find what makes them happy and healthy.

Even though it was irrational to think people would come to a tiny town in the middle of the Andes, we also had the sense of ”If you build it they will come.” And people have found us. In a less than year and a half we've had over 300 people from 30 countries, of all different ages.

Most people find us by word of mouth. Travelers find us through Trip Advisor, Facebook and Airbnb, but most discover the house from a suggestion from a friend. 

The majority of our travelers are people in transition, looking to spend some down time doing some soul-searching, working on a passion project like writing a book, creating art, or getting in shape and reflecting on what they want to make of their life. Most friends stay for over a month and end up feeling like family.

4 ways Megan’s days have changed:

I tend to flow with where the day goes. 

I've never known a life where we weren't forced to live by the clock. Time doesn't exist the same way down here. We still work hard, cook, clean, take reservations, communicate with future guests, are present for current guests, design logos and websites, and build furniture. But nothing is forced. 

I find myself much more focused when it is time to write or design. 

People connect on a much deeper level when they aren't behind the glow of a screen. We don't have internet in the house right now. Then I go to use internet with a list of things I need to accomplish. 

I get to be a momma. 

I'm momma to travelers and my amazing son. In the hectic life of LA living, I don't know how i would have found the presence of mind to be here for others the way I can be now. I found the joy of caretaking, nurturing, listening and seeing people through great triumphs or challenges. I am so stinking grateful for not having to worry about maternity leave or the crushing costs of healthcare with having my little baby. 

I get to be partners with my partner. 

We get a lot of time to work together, work things out, learn and grow without constant distractions, stresses and "real" jobs.

Second-guessing is part of the job

I have never been particularly spiritual, but stepping out into the abyss builds your faith in yourself and the universe in a way I have never known. There were moments where we were down to our last penny but felt somewhere deep down, we should keep going. Many times we had no idea how we would make things work and then someone would come in and donate money, give gifts or bring in friends to cover the rent.  


I’m reminded of a part in the I Ching about how to make progress. It says that a wind that constantly shifts directions just stirs things up. A wind that moves in a slow constant direction shapes the world. Sometimes we'd think of changing directions, about giving up or starting something new. But by slowly building, we have created a beautiful house full of the most amazing people I've ever met.  

I also think of an expression that is used a lot by the indigenous people here: "poco a poco" or little by little. The best businesses I've seen are built brick by brick with a solid foundation. They create a great service at a reasonable price that people are willing to pay because of what they receive in return.

We've learned not to become too attached to anything but simply go with the flow and take the path of least resistance.  What used to sound like bohemian cliches have become very real to us in our simple life. We learn lessons, we make decisions, we shift slowly and purposely.

I've learned to truly listen to my inner voice of what I want and need and to honor it, rather than "shoulding" myself. Based on paper, taking a high-paying, high-powered job made much more sense, but I’ve discovered that creating my life with intention and thoughtfulness brings the rewards of being part of something i believe in. It's really the best gift I've ever given to myself.


Need To Know

If you visit one place, Megan recommends Iguazu Falls, Brazil.

Follow Tres Osos' gorgeous Instagram @casatresosos and Twitter @tresososperu.

It has a Facebook page you should follow too. 

Also, learn more about Megan Youngmee's creative work.