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. 


We lived through Hurricanes Irma and Maria. Here's what it was like.

The essentials: We're safe, Scallywag is still afloat, and we're waiting for an evacuation flight this Friday to spend a little time with power, water and better connectivity in LA before we regroup and decide what's next for us.

In the last month, Jon and I have lived through both Irma and Maria on Puerto Rico. In the process we've witnessed some amazing things and accidentally organized a grassroots effort to bring help to the islands through SailorsHelping.org

Jon and I have shared day-by day-updates from right before Irma until now on our personal Facebook pages, so I took the time to combine our stories to give you a sense of what it's been like in Puerto Rico this month. I've reposted our stories in chronological order from shortly after Hurricane Irma. We may overlap a bit in our stories, but hey, when don't married couples talk over each other! We'll continue to share our stories as things develop. 

The day after Irma with water but no power, we started to act. We threw up a website and facebook group and started collecting donations to send to stricken areas across the Caribbean. IN the 90-degree heat, Jon and I slept little but worked for hours at the Doubletree, organizing relief efforts and meeting people across the island who also wanted to help. And this is where we pick up our story. 

In that last 24 hours, we've personally coordinated more than 15,000 lbs of goods onto planes to Anguilla and Tortola for immediate relief. And when I say personally I mean: we personally purchased them, weighed palettes of stuff ourselves, I personally drove a cargo truck back and forth across SJU's tarmac and we were inside these cargo planes loading them. Our friend personally flew one of the chartered flights, with Jon on to take photos of the damage and see what else we could do on the other end.

We did this, with our own hands, with the help of awesome new friends. I've never done anything like this before. It was amazing to know that we were personally responsible for getting incredibly necessary goods to the places that need them.

Also, we FINALLY got power back in our area of the city, after 8 days of working without power off our hotspot and battery packs. I was ready for my first hot shower in a long time and a little celebration.

But as I left the airport and walked into my friend's house for a much-needed drink, I learned that what's left might be wiped out in just 4 days with another cat 3/4 hurricane, Maria, headed our way.

That all that good work may go to nothing. 

That Puerto Rico, still without power in many places and low on storm-prep and recovery items like generators, tarps, building materials, and emergency rations because we sent it all to the neighboring islands who need them, will be royally fucked if this thing actually hits. 

That our boat has a 50/50 chance of making it through the next storm depending on where we choose to put it in the next 12 hours.

That the house we fell in love with, that we just put an offer on yesterday, may or may not be in the path of a direct hit. 

That my business, from which I've already been struggling to keep up with (thank god for good talented friends who have taken over in the short term) might be out of commission for another two weeks or may even have to fold if I am unable to get internet and connectivity after this storm.

I have no words for this moment. There are no right answers for how to handle the next few days. Please keep us, our boat, and all the people in the islands facing this in your thoughts.



Our two primary options on where to keep Scallywag during the upcoming Cat 3-4 Hurricane Maria. The mangroves near Salinas or the newly constructed "hurricane hole" of a marina, Puerto Del Rey, in Fajardo. Neither are good options. Based on all of our friend's recent experiences, we are honestly preparing for the worst. Going to unload all our important things today and make a decision likely tonight or first thing in the AM on where to bring her. 


We just stripped Scally of everything valuable. I left my favorite bathing suit, her pretty pillows, our whiskey glasses and good whiskey and my most used cookbooks, just so she could be sure we'll always come back for her. She can't sink if she knows how much we love her. ❤️ Cat 4 predicted, 120kt winds.
We just toasted her from the best seat on the boat, and poured a little out for her too. She loves a good whiskey on a balmy night.
Headed into the mangroves with her soon, so that we can find a cozy spot for her in first light. #mariayouasshole


We spent the last two days prepping Scally for what is most likely her first and only Cat 5 hurricane in her 43 years. It was one of the hardest things I've ever done.

If you've never owned a boat, the only way I can describe it is a combo of a pet, older and wiser mentor, and a home.

Scally is our most valuable possession. Not in terms of cash value, but in terms of impact to our lives. She has largely impacted or shaped four of our nine years together. We got engaged on that boat. We sailed 3,000+ miles on that boat. She is more than a boat, she is family.

We did the best we can... we ran eight lines and threw out two large anchors with more than 350' of chain total. We're hoping for the best, but prepared for the worst.

Hurricane Maria hits tomorrow as a direct hit to Puerto Rico as a Cat 4/5. We had a near miss with Irma and still lost power for eight days in my neighborhood. We're going to ride out the storm in a 300 year old concrete building in Old San Juan and should be totally fine, but I'll likely be offline for a little bit. Will check in when I can. Keep us and Scally in your thoughts.


I think I can safely say the last two days have been the most brutal two days of my life. With Maria shifting, we're looking at potentially losing Scallywag and our remaining possessions in our apartment in San Juan that we moved into this month, which is in the flood zone.

We spent three days sleeping only a few hours, wading around in mangroves, tying more than a dozen lines and stripping her boom, sheets, solar panels and hardware in unrelenting heat. Scally is incredibly snug in her spot and we feel like we did the absolute best we could do for her. But it was hard, physically and emotionally. The last step was to tighten her lines at 3 o clock, once boats stopped entering the mangroves. If you do it too soon, people will cut your lines to find their own safe harbor.

A local cruiser whom we trusted volunteered to do the final line tightening since there was no way for us to wait until the last minute for the lines and get to our safe house for the storm in time. We know him loosely, but drove his wife to her safe house. He passed the last storm with us too. We've texted him three times to confirm they were tightened. All the messages have been read but we've received no answer. We're not sure if that's because he can't break the bad news to us or because he's already lost connectivity. My heart is in my throat.

As for us, we've lost power and have limited cell coverage but also have sat text messaging so I'll try to keep y'all up to date while I can. We're well stocked, (have all our emergency supplies from two boats) in a 200-year-old building with really thick walls. Both euro and gfs models show that right now San Juan may miss a direct hit, which is good. Landfall on the east coast of PR is imminent.

If you're following along, Scally is in Los Hobos mangrove next to Salinas and we're on Calle Sol in San Juan. Half of our friends have their boats in the same mangrove, the other half chose Puerto Del Rey in Fajardo. We all live on our boats.

We're with one other couple, whose boat is in Fajardo. Depending on the model, a direct hit on one of our boats means the other is spared. We're all hoping for the best but adamantly rooting against each other. None of us like sports but realized, over a round of dark and stormies last night, that this might be what being a diehard sports fan must feel like.

Keep us in your thoughts, folks. The next 24 hours are going to be really, really rough.


Facebook: Victoria Fine Checked In as SAFE.

The damage in San Juan is mind blowing. We checked our apartment today - Unbelievably, the flood zone stopped literally at our front door. One house away, the water is waist deep and people were kayaking and dinghying by with outboards. Checking on Scally today, will share updates when I can.


Made it through to the other side of Maria. People are out surveying the neighborhood. Things are pretty solid in Old San Juan structurally as everything is solid concrete. I have had word of pretty major flooding in other areas and that the power is out on the entire island - likely for months.
But so far Tory and I are fine and we have gotten word that our actual apartment a block from the beach did not flood. No word from anyone near the boat, but will try to find a way to get there tomorrow. Not sure it will be possible yet.

This photo is essentially how we spent most of the hurricane -- we all have different providers, so we were constantly waiting to see who would get the next intermittent signal for updates...



There is a saying in Spanish that goes "cuando te toca, ni aunque te quites; cuando no te toca, ni aunque te pongas."

It roughly means, if it's your time to go nothing will stop it from happening, if it's not, you couldn't make it happen if you tried. At least that's how my friend Paulo explained it to me as we were driving to check on our boats today.

The morning started when I woke up at 6 a.m. unable to sleep. I knew that my mission for the day was going to be to find a car to get to the boat. I walked outside and two neighbors were talking. I asked if either knew who owned the jeep parked in front. As luck would have it, the one woman actually was the owner. But in typical Hollywood fashion, she had a broken arm and we would need to bring her to the hospital for treatment before borrowing the car.

We drive from one clinic to the next, finally finding one near our actual apartment that we didn't stay in - as it's one block from the ocean. We decide to make a quick stop to make sure it's ok and find a guy with a fully engaged outboard engine dingying around at the corner of our street. We go the long way around and luckily find that the flooding literally stopped at our front door.

First stop, a success.

Next, we drop our neighbor at the emergency clinic with Tory, while Paulo and I head out to Salinas on the south side of the island.

The trip from north to south is nothing short of post-apocalyptic. We could see the line of destruction of where the hurricane track actually crossed the island. Not a leaf remained on any tree for a good 20 miles.

The road was beginning to be cleared by volunteer teams hacking at the fallen trees with anything from a hand saw to a chainsaw. The flooding had largely gone done on the south bound side of the road, but the north bound still kept smaller cars from passing at certain points. Jungle rules applied and cars were crossing sides of the highways as needed to get to where they needed to go. I was very happy to be in a large Jeep today.

We arrived in the small village near the mangroves around noon. People walking around shared stories of their roofs being blown off and the flooding extending to their doors. We went to one small private dinghy dock and called for any vessels in the Jobos Bay Mangroves to give us a lift to our boats. Sure enough, someone showed up just a few minutes later.

As we pulled up to Scally, I could see from a distance that she was still floating - despite the boat in front of her being thrown well up into the mangroves. Something referred to as being "high and dry" - not a good thing.

I climbed aboard and it immediately looked like she had been through a battle. While she emerged victorious, she had definitely received some wounds. The mangroves also stain the boats and water red, so her decks and hull were not just showing the scars, but actually appeared to be bleeding.

As I inspected the damages, it became clear that the surge and wind had picked her up about three feet and thrown her into the mangroves. You can see a spot in one of the photos off her aft quarter where the mangroves are all worn down and broken - that's where she rode out part of the storm.

As the wind shifted, she got sent back out away from the branches, but one or many took hold of her and didn't want to let go. Ultimately, it took her back railing and stanchion, the helm's compass, bent the bracket for the top solar mount, broke off part of the teak cockpit trim, and ripped up a piece of the genoa track on the toe rail. It must have been quite the fight, but scally emerged.

As the saying goes, it was not her time to go.

Numerous other stories came out of the other boaters in the groves - many of which stayed on their boats - many of which also actually broke clear free and were blown all around the mangroves or well up into them (high and dry). In total, there were about 20 boats in the mangroves riding out Maria and I'd say that 5-6 of them either broke loose completely, ended up resting on top of the mangroves, or both. In Salinas harbor proper, it was WAY worse. I'd say 60-70% of the boats there ended up on land.

For us now, we are lucky to have a generator from our boat and will be charging our various devices once a day. Our main issue now is fuel and connectivity. In about a week, it will be good and water, but at least the pizza place down the street started doing take out today, so it was an overall good first day post-hurricane.


The days are a thousand hours long right now but the flashes of goodness are just as prolific.

Yesterday, I helped a neighbor who broke her arm after the storm find an open hospital to be treated. We spent the morning at the emergency room.

There were no orthopedists on duty, but a friend of our neighbor happened to be in the emergency room, as she had heard about the broken arm and knew of an excellent orthopedist to treat her.

There was no way to reach him, but as we were sitting, waiting for the X-ray results, the friend saw the orthopedist's wife walk by. She yelled out. The wife stopped and we explained the situation. Even though the doctor didn't work in the building, he happened to be in the other room to pick up supplies. He treated our neighbor immediately and we were in our way.

Outside, we picked our way over 200-year-old trees and downed telephone poles. The scene around us was post-apocalyptic.

The friend from the emergency room was acting strangely as if she was in shock. I asked her if she had a safe place to stay. She said she was still figuring things out and I invited her back to stay in a safe place while she figured things out. She got in acab with us home.

This was a mistake. Our neighbor quietly whispered that this wasn't a shell-shocked friend but a crazy lady that regularly squatted in people's houses and wouldn't leave for months at a time. And I had just let her into our borrowed home.

Maybe it was the storm that took it out of me, but I just didn't have it in me to kick her out again. So I made our friends, both SVU prosecutors, do it for me. For some inexplicable reason, she wouldn't leave without a new t-shirt to take org her. So I gave her literally my last clean shirt off my back. Later, over wine, we all agreed this was the appropriate punishment for making my friends kick a crazy lady out of the house.


By 7 a.m. the house is awake and moving. Without electricity, and the constant presence of man made light, our hurricane clocks have reset us to rising and sleeping by the sun.

The first win of the morning is when Andrew realized that we can redirect our roof's gutter to a (clean) trash can to collect rain water. Without running water, this is now our back up that we use for flushing toilets and other household needs.

Something I never thought I'd know: it takes about two pitchers of water to get a regular (non-low flush toilet to flush).

We follow this win with a quick walk around the neighborhood and find several local restaurants serving coffee or breakfast sandwiches as takeaway at the door. The spirit of resilience here, once again, shining through.

When we officially set out today, I have two missions: gas and coke (the soda variety of course).

We knew that we will have to get back to Salinas to actually move Scallywag out of the mangroves, however the trip down and back takes half a tank of gas in the jeep and we are now down to only a quarter tank. The only way we can make the trip is if we find more gas.
We get word through a relatively active WhatsApp group that a Total gas station on the other side of town is still pumping, so we set off in that direction. Unfortunately, when we get there it had already run out of fuel. We try several others also with no luck.

As we are about to give up, we spot one from the highway! Of course the line of cars is a mile long, so we opt to grab our jerry can and wait in the foot traffic line. This turns out to be a bad mistake as we eventually realize that cars take up much more space than humans and the vehicle line is actually moving much quicker. Live and learn.

As we stand in line, Paulo manages to sneak in and grab me a coke! Mission one accomplished. However, I get greedy with the gas station being so well stocked and sneak back in myself to emerge purchasing a full case! No more worrying about that issue.

As we continue to wait in the line, hour after hour, the mood feels like it needed a bit of uplifting. So Paulo and I once again find ourselves sneaking past the line and into the convenience store to purchase about 50 beers that we then take outside and distribute to the line. Much happier people! At least for the short term.


By hour four, people are starting to get hostile. Of course, this is also right as the three of us get to the door with our jerry cans (we have now borrowed one from someone later in line so we can quickly fill the tank of our car parked around the corner with one, while filling another - we manage to get three cans worth with this little trick). But right as we were get to the door, a yelling match breaks out that almost threatens the entire operation. The owner comes out for a second and says that the station is closing as a result and this situation and it takes the rest of us to diffuse the situation to keep things going.

After four hours, we leave with a full tank of gas, an extra jerry can full, and a lot of friends from our free beer move.


The bonus of the day is coming back to Old San Juan and finding El Hamburger has already opened their doors. This is one of the best hamburger joints ever. Despite having a chunk of their roof ripped off, they are still serving happy customers.

And later in the evening our neighbor invites us to an amazing candle lit dinner in her courtyard. Puerto Rico may be knocked down, but the county is far from knocked out.


In the mountains, it looks like the earth has been scorched, but it's just earth overturned by the force of the wind.


I am becoming accustomed to living life based around daily missions. This some how makes me feel like I am accomplishing something, even if it is the most mundane task.

Day three's mission: Get back to the boat and take her out of the mangroves.

Paulo, Tory and I set out early. Driving the same roads we did two days earlier, it is clear that progress is being made. The roads are cleared of all but the biggest trees and there are many more cars making the trip.

We arrive to the small village near Salinas and say hello to our new friend Pablo - the young fisherman who owns the house where we left our dinghy. We quickly realize that we left the key to this dinghy back in San Juan and need to hitch a ride to the boats. Of course with the gas shortage, nothing is easy and we had to pour fuel from the locked up fuel tank in Paulo's boat into the tank for Pablo's motor... right as it started to pour down rain.


We get to the boat and slowly start pulling in all the lines and chain. Doing a rough count, I'd say we have more than 800' of line, 350' of chain and two anchors out, so this in itself is no small task.

A few hours later, we head back to Salinas with Scally. This time, we are able to more closely survey the grounded boats that line the shore. I count more than 50. It sinks in just how lucky we are.

We drop anchor as there are no docks to return to and, as we begin setting up the solar panels and prepping the boat to be able to leave her for a little while, we hear the familiar boat name "Desue" on the VHF. This boat is a trawler with two older couples on board that was next to us in the mangroves. Their daughter, Lucy, had reached out to me on Facebook looking for information on them and I was the first person to be able to tell her that they were alright. I jump on the VHF and convey this to Desue and they are eternally grateful for helping bridge the communication gap as the majority of the island is still without any signal. A small side win for today's mission.
As we finally wrap up prepping the two boats, we realize it's now 6:20pm and curfew is still in effect starting at 6:00. We say screw it and decide to risk it with the hour plus trip back to San Juan. The roads are dark and dangerous - our lights barely work. We make the majority of the trip drafting behind other cars to use the light of their more powerful headlights. Good news is that we pass at least four gas trucks going back and forth bringing fuel across the island.

By 8 p.m., we're home and exhausted. We go to bed early. Another mission complete. On to tomorrow's.


We'll continue updating with future blog posts as time and connectivity allow. In the meantime, please send good thoughts to the islands. They need each and every one.

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




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. 


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.)


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! 


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. 


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. 


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.