2016: My Nomadic, Open-Hearted Year in Review

On the very first day of 2016 I landed at Liberia Airport in Costa Rica, alone.

I didn’t have a ticket home yet, and I didn’t have much of a plan. All I knew was that I was single, I was “location independent,” and I was totally overwhelmed by all my freedom.

The week before, I sobbed in my mom’s lap about how I’d never thought I’d feel lost or depressed again. I’d spent the first 27 years of my life feeling lost and depressed, but then I found my fucking purpose. I was pursuing my dreams full-time, on my own terms, and making an impact. Shouldn’t that be enough to be happy?? Ugh.

A few months before, I’d made some big, bold (terrifying) choices.  I had moved out of NYC, given up my (insanely lucrative) training career to focus on building my business online despite not knowing a single thing about business. I figured after that everything would just… I don’t know, fall perfectly into place?

So, fast forward. Crying to mom while my old friends Depression and Confusion hover nearby, and deciding to book a ticket somewhere warm and beautiful because fuck it.

I put feelers out on facebook and glommed onto a vague plan to maybe meet up with some internet friends in Costa Rica, later in January. I booked an AirBnB treehouse in a random town, and I arrived on New Year’s Day with no idea how to get anywhere, or what as gonna do when I got there.

After a series of appropriate mishaps (aka it was New Year’s Day so none of the buses were running and no cabbies were out), I finally arrived at my treehouse. It was late at night and I could hear the ocean.  I was surprised. Am I by the ocean? 

The apartment was adorable though, the weather was deliciously warm, and I was starving. I put on a pretty dress and started walking toward the lights nearby, hoping that lights meant food, and that I was somewhere with menus printed in English. As I sat there that first night, eating pizza of all things (it was the only thing they had left) and watching the people around me, I was filled with a sense of yes-ness. This was where I was supposed to have come. Good things were going to happen here.

I was right. The next morning I discovered that I was indeed about a 60 second walk from the beach, and that this was (shockingly) a surf town. Literally everyone was there for the sick waves, bro. 

How did I not realize this? Easy: when I booked my trip, I did exactly zero research. I wasn’t interested in being prepared, I was interested in being gone.

Those two weeks were nothing short of soul-restoration. I spent tons of time by myself reading, writing, resting, swimming, praying, and re-connecting to myself. I walked everywhere, watched every glorious sunset, tried surfing a few times (full disclosure: I sucked and dated it), made a friend to practice spanish with, and soaked in the healing warmth of the sun.

By the time I left Santa Theresa, I was tan, well-rested, and filled with purpose and clarity again.  I was… happy.

Then I traveled five hours to spend a few weeks living with a guy I had met once at a wedding years ago, and his fiance. Seem weird? I guess it kind of was, but I’ve made a habit of meeting internet friends in intimate real-life situations, so why not? Turns out, Jon and Alison are amazing, and my time spent with the two of them felt like I had  gotten a VIP invitation to join a beautiful little nomad family.

Our daily routine was blissful: work during the morning, go on a little adventure/exercise break, then return to work until dinner. Alison is a naturopathic doctor and an amazing cook, and I swear I ate healthier with them than I ever have in my life. On my birthday, Jon and Alison surprised me with a beautiful day including zip lining through the jungle, a massage, dinner, and (somehow) dancing. It was touching and beautiful and I started to feel really sad and stressed about leaving. 

One night during dinner Alison talked me into staying for another few months. (You can stay in CR without a visa for three months, so that was how long they had their apartment.) Their other roomies were coming back so I’d have to figure out lodging, but I figured what else am I doing?

Finding last minute lodging was tough because it was high season, but I had the sense it would all work out, due to my incredibly excellent “luck” lately. One day I was out for a run on the beach and decided I didn’t feel like running anymore, so I stopped for tacos and a beer. There I met a bartender whose aunt had a house in a nearby town, so…you know… I rented it.

By this point I was driving everywhere on my beloved ATV, so a 20 minute drive to and from a remote little local town was actually a thrill. I drove by cows and goats and sheep and just blissed out every day. 

Costa Rica was such a desirable destination that many of us had visitors and friends throughout the trip, and it was always wonderful. Friends came and went so often that it felt like our family was constantly expanding. One of the highlights for me was having my best friend from college come to visit so we could spend a few days laughing, sunning, and catching up on each other.

One thing I haven’t mentioned yet here is that Jon and Alison’s roommates were Molly Galbraith of Girls Gone Strong, and her boyfriend Casey. I had met Molly years before at a wedding, but had never gotten to spend much time with her. I knew that she was smart and driven, but what I didn’t know was that she (and Casey) are also fucking hilarious.  

innertime was just as likely to be a place where everyone helped one person through a work problem as it was to be all five of us laughing so hard our abs hurt.

I learned a few important things while I was living with these two amazing couples. Watching how very different they were from each other, and seeing how both of them really just worked, I was fascinated and inspired. 

I had felt like maybe the single life was better for me for a variety of reasons, but watching these guys I thought… well geez, that looks pretty awesome. I also realized that I really needed to be surrounded by other entrepreneurs. I hadn’t even realized until then how isolated and lonely I had felt in my work, but

Some other notable things that happened in Costa Rica include me getting a case of food poisoning so intense I was praying for death, many encounters with scorpions and giant spiders, riding horses on the beach at sunset, and some incredibly work productivity. I created and launched several new courses while I was there, learned for the first time how to create sales pages and white sales copy, and got a clearer picture of what I wanted to be building.

The moral of Costa Rica for me seemed to be: happy, healthy, tan, and productive as fuck.

I spent about a week with my family after I got home from Costa Rica. Just enough to unpack and re-pack and cuddle my adorable new nephew, before heading to the Thai Embassy in NYC. After that I hopped on a plane to celebrate the closing of snow season with my little brother in Montana. We snowboarded, partied, and reconnected for a few days before I headed out on a thirty hours flight to…

…Thailand.

Fun fact: Thailand is a country in Asia. That was quite literally the only fact I had in my back pocket the day I landed. Despite a few days booked at a hotel to sleep off the absolutely crushing jetlag, I had no plan whatsoever. No housing, no contacts, no idea what Thai culture was like. All I had was a ticket to leave, three months later, from a different city.

Chiang Mai was supposed to be a hub for digital nomads like myself, which is why I chose it. Plus because it’s super cheap so I could (and did) live like a goddamn on very little money. Mostly I was following the gut desire (born in CR) to be surrounded and supported by like-minded entrepreneurs. I figured: so far buying tickets to random places with no research had panned out pretty well, so why stop now?

Just to be clear, when I say I didn’t know anything about Thailand, I’m not exaggerating. Early on, a new friend told me I had to check out Cambodia since it was right nearby, and I laughed and corrected her, saying Cambodia is actually in Africa. 

I was so confident in this totally false statement that she responded really slowly, like she was talking to a child, or a crazy person.

“No it’s not. Cambodia shares a border with Thailand. I was there a few weeks ago.”

“Jessi, where do you think you are?”

Ah. Well. This was sadly not the last time I would be horribly embarrassed about my lack of world-knowledge. Over and over again, as I met people from all over the world, I would feel incredible shame to be from America. Our education system is so self-centered that I’d never heard of whole big countries like Laos, and if you’d asked me previously where Bali or Malaysia were, I’m not sure I would have even named the right hemisphere. 

Mind you, of course, I could have done some travel-research to find these things out before my trip. But nonetheless, it was shocking to realize how little value American public schools place on Asian history and geography.

Before my trip, when people would ask me if I knew anyone there, I would say “No, but that’s ok, I’ll make friends.” People thought this sounded crazy, but I just knew in my heart it would be fine.

The first week in Thailand I met two random French-cum-Canadian men in a coffee shop. They were accountants who had quit their jobs and were traveling Asia together for six months, and we fell easily into a friendship.

One of these wonderful men went off to travel on his own for a while, and the other stayed in Chiang Mai to see if he could put together a plan for a business that would allow him to become a full-time digital nomad. (I’m convinced there truly is no better place in the world to do this.) We very quickly found a group of young nomads who met every Friday to share skills and advice, connect, solve problems, and socialize.

This community of nomads was easily the best part of Chiang Mai for me, and I felt supported and nourished in every way I had been hoping for. The people I met were from every country imaginable, and any given dinner table with them was sure to include at least half a dozen unique accents and tons of laughter.

Interestingly, I didn’t meet that many Americans. A few, for sure. But far more Canadians, Australians, and Europeans. At a social gathering I was asked constantly by curious foreigners about the whole Trump for President thing. They genuinely wanted to understand: who are the people supporting him? Is this a joke? 

A few guys from Denmark pointed out that in all their travels around the world, none of them had ever met a single Republican. We realized with horror that it’s because Republicans don’t really “travel.” They “vacation.”

Is that a big blanket statement? Sure, maybe. But I’ve done a ton of traveling myself, and it seems to stand true. I genuinely believe that traveling the world irreversibly opens your heart and mind to other people and cultures in a way that would make it nearly impossible to fall for the Republican rhetorics of racism, sexism, and the myth that America is the best while the rest of the world is backwards. I believe that if more people traveled like this, Trump wouldn’t be our president-elect. (You don’t have to agree, but this is my story and I’m telling you what I saw.)

Everywhere I’ve traveled has been filled with open-hearted and open-minded people. People interested in the world, interested in bettering themselves, and interested in learning and growing and meeting people. The people I met this year consistently valued experiences over belongings, and understood that happiness is an inside job. Living in Chiang Mai was fuel for my soul. 

After living in a sleepy, tiny Costa Rican town, I was also thrilled to have access to interesting goings-on again! Chiang Mai has gorgeous temples, a crossfit gym, cows just chillin mid-city, and a totally amazing nightlife with open-air clubs, where everybody actually dances their faces off. (Literally everyone dances. All night. You wouldn’t go if you didn’t want to dance, because there is no pretense of being too cool there. It was heaven on earth.)

Plus the food… oh my god, the food. For a dollar, I could get a filling dinner of the best Thai food I’ve ever had in my life. And the coffee scene was out of control. Legendary and competition-winning baristas in world-class coffeeshops, on every corner.

I mostly spent my days working in coffee shops, and spent my nights drinking, playing pool, and dancing. For the rest of my life, there will probably never be anything as refreshing to me as the first sip of a Chang beer poured over ice while sitting outside Wanz Cafe in the still-sweltering heat when we quit work for the day at 6pm.

Plus, the highlight of Thailand was the fact that I was able to bring my little brother to visit for two weeks.

I’d been saving money for several years in an “adventure fund” to take Jason somewhere cool, and was finally able to cash it in.

This fund was based on the pay-it-forward principle; I would not be who I am were it not for some adventures I was taken on when I was young and broke. I was insanely lucky, and the adventures I was taken on permanently shifted my worldview and trajectory in life. I consider it my duty and my pleasure to offer the same kind of experience to other young people, starting with my brother.

For two weeks, I would wake up and find Jason at the cafe downstairs, where he was playing hide and seek with the children of one of my neighbors. Then, since Jay ate about ten meals a day, most of our time was spent as a sort of Thai gustotory scavenger hunt. Before we even finished lunch he would have already planned where we should head next for an early dinner, and would typically stop on the way there to buy snacks on the street. 

It was such a yes experience, having Jason there, introducing him to my nomad life, seeing his heart and mind expanding, and receiving the soul-nourishment of being together in such a magical place. 

After Jason left I dove back into work, launching my Empowered Women course again, and writing a new one called Make Friends With Your Feelings. That shit poured out of me over the last few weeks in Thailand, as though I wasn’t writing it at all, but rather receiving it. While riding the creative tidal wave, I also dyed my hair silver, then blue, and prepared to leave Chiang Mai and return to “normal life.”

Except “normal life” was really to begin with a thirty hour trip to Toronto, where I was attending Jon and Alison’s wedding! 

To kick things off, I got super sick at the end of the flight, and had to sleep for two days in their spare bedroom. Whomp, whomp. But then I was reunited with my Costa Rica family, including Molly and Casey!! We prepared for wedding festivities and socialized with our Toronto fitness friends, then I got all fancied up with my friend and date-for-the-evening Rog Law, and boated over to a gorgeous little island club and watched our friends get married. It was beautiful.

Ok but now for real- back to normal life!

Except that I have no normal life anymore. 

My plan was just to stay with my mom and spend time with family for a few weeks before heading to NYC for a month in September. There, I planned to do my first ever Empowered Women Project Workshop while I finish working on my TedX talk, which I would be giving October 1st. The talk was the whole reason I was stateside, and I needed some time to focus on it.

So, great. “Time with family” included my older brother’s birthday party, where I saw his best friend, Tom. I have known Tom since I was eight years old, and we’ve been somewhat distant friends over the last twenty-one years. We had a really fun and giggly time together at the party, and over the next few days I tried to process some new information: I think Tom is hot.

This was a very confusing fact for me, since he’s this super weird guy who was friends with my high school ex boyfriend and my brother. Except that at sleepovers he would sometimes stay up all night talking to me. And technically we “dated” in 5th grade. Oh, and, I was his first kiss.

So long story short (ha! This is already almost 2500 words) I ask my brother what he would think about me asking Tom out, and I receive not just a blessing but a gushing soliloquey of praise and support. Tom and I meet for drinks one night at a bar. I tell him flat out that I’m leaving in a few weeks, I’ll never live in Syracuse again, I don’t believe in marriage, I never want children, and I’d understand if he wasn’t down for that. He loves living here, definitely wants a family of his own soon, and tells me “there’s no way I’m giving up the opportunity to spend time with you.”

We end up kissing that night, and become somewhat inseparable for the next few weeks.

Naturally, I’ve made plans for my month in NYC, and I want to honor them. But the thought of leaving starts to feel like less and less of a good idea. One day I tell Tom that I want us to keep getting closer, and he tells me it’s hard because he knows I’m leaving soon.

“What if I stay for a while?” I ask.

By the time I head to NYC I plan on staying with my mom “through the holidays” to figure out what’s there with Tom. I already know it’s Big and Important, but I don’t want to rush things just because I’m homeless, so I agree only to stay a bit and “see.”

When I return, it’s to give my TEDx talk. I’m terrified, because what I’ve written is excruciatingly personal and vulnerable. It’s about sexual assault, and the experience of trying to love yourself while living in a female body in our culture.

The first time I perform a stumble-through for Tom, he says to me, with tears, in his eyes “I’m just so honored that you like me.”

The talk goes amazingly well. Since it’s my second one, I’m a lot more comfortable with the whole concept of standing on stage and giving a memorized speech.

It feels powerful and truthful, and the response I get from the women in the audience afterward is both exhilarating and devastating.

Woman after woman waits her turn to speak with me for a moment, many of them sharing their personal experiences with sexual assault, and all of them at least affected on behalf of someone they deeply care about. I go to a fancy dinner with my family to celebrate and later on I cry a lot and sleep for a long time.

Soon after, I realize a few things with alternating ecstasy and rage:

1. I’m going to move to Syracuse.
2. I will probably marry this man and have his children.

I assure you, these realizations did not come easy. In fact, each one came with waves of resistance and pain and fear and healing and courage. Moving here means I would have to handle some shit I vowed never to be a part of again: upstate NY winters, driving a car, having a “normal life,” and living somewhere that doesn’t inspire me. Fuck that. FUCK ALL THAT.

But it didn’t matter. I was spending tons of time with my mom and my older brother and my nephew. Tom and I were having an amazing time together. I was… happy. In Syracuse. Ugh.

We didn’t mean to move in together so soon, but circumstances rang and we answered. Tom and I moved into a little one bedroom apartment in a one-stoplight town. I started re-learning how to drive a car. We enjoyed the beautiful fall, and I watched my nephew learn to talk. We made it through an election that tested the limits of my ability to keep my heart open.

The interesting thing to me about re-meeting Tom now is that I used to be someone who completely lost herself inside of every relationship. I was sure I wouldn’t get married for a lot of reasons, but one of them is that in my view, marriage is the death of growth and expansion, and growth and expansion are my highest values. I didn’t think I could ever continue my personal growth and expansion with another person, because I had always become smaller, thinner, less of myself once I had another person’s feelings to deal with.

But with Tom, I felt strong. Sure of myself. Somehow aware that I wasn’t going to shrink here; that his personal need for growth and expansion would make it ok for me to show up fully, forever. That everything I had solidified about myself this year were finally being reflected in my ability to maintain my bigness with another person.

In November, we spent a week in Mississippi to celebrate Tom’s birthday and to visit my dad and his wife. My little brother and his girlfriend were there, and we all spent the kind of amazing day in New Orleans that will be family legend for many years. While traveling, I had deeply missed spending time with my family, and I felt like I was finally catching up.

By the time we returned home, winter had arrived in earnest. December has included a lot of settling into our new apartment, settling into our new relationship, spending time with my family, and (of course) working.

I don’t know what 2017 will look like, but I do know that 2016 was exactly right. All the travel, all the chaos and pain, all the massive growth and learning and expanding, it was all exactly right. Traveling alone has been one of the most incredible and life-affirming things I’ve ever done, and despite having an apartment and a boyfriend, I have no intention of giving it up.

In a few weeks I’ll be going off the grid completely for two weeks to Peru. I’ll be flying solo, of course, and it’ll be something totally brand new: a meditation, yoga, and ayahuasca retreat for massive, intentional healing. No wifi, no electricity, no work. I’m scared and excited to be doing something so big and new, but thanks to the year I’ve had I’m more confident and relaxed than ever.

I know I can handle anything, that I am enough, and that life is constantly giving me exactly what I need. Don’t get me wrong though, that doesn’t mean life is constantly making me happy.

Sometimes what I need is to be scared, or lost, or lonely, or angry (ahem, Trump). Sometimes the gifts I am given come in the form of pain, and heartache, and loss. But since they help me continue my path to healing and growth and learning how to keep my heart ever-more open in the face of challenges, they are gifts nonetheless.

2016 taught me how to know and maintain my self-ness, no matter where I am, what I’m doing, or who I’m with. I can’t wait to find out what 2017 will bring.

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