Hi from Greece!

Updated: Nov 2

Some thoughts on travel, over the years.

Hey friend,


I’ve been in Greece with my mom and brother for the last week, and I still have one more week to go. As such, I want to share a few thoughts about travel, identity, and growth that have been swirling for me.


Santorini, Greece
Santorini, Greece

To begin, I should say that I didn’t travel much as a kid. We didn’t have the money to do fancy vacations or anything, so we mostly did low-budget excursions like camping. And I didn’t even think much about that until I got to high school, and started thinking about doing a foreign exchange program.


I don’t remember when I knew I wanted to be a world traveler, but I do know it was sparked by books. I loved reading because I loved adventuring, and by the time I was in high school I just knew that as soon as I had money and independence, I would use both to see the world.


Anxious to get started ASAP, I raised money for the tuition, graduated high school early, and spent the last semester of high school living in Chile with a host family. Because the exchange program I went with was badly run, it ended up being a terrible experience…. but it also blasted my mind wide open.


La Serena City, Chile
La Serena City, Chile

Having grown up in a conservative family in rural/Christian/Republican upstate New York, I took for granted a few things:

  • America is the greatest country in the world, and everyone else in the world loves and admires us.

  • George Bush Jr. (the U.S. president at the time) was a great and popular leader.

  • People in other cultures are weird, wrong, and backwards.

This makes my skin crawl to write, but it’s important to do so, because–as you can probably imagine–my semester in Chile absolutely demolished many of my foundational beliefs about the world. At the time, people there hated George Bush Jr, and there seemed to be endless local protests and displays of violence about their hatred for the U.S. as well. It was… well it was devastating, really.


But it was also important, because I suddenly had a brand new awareness of how small and biased my previous perspective had been. And that insight drove the direction of my life thereafter.


That semester also demolished my (bigoted and racist) belief that people from other cultures were so impossibly different from me. I remember just a few days after arriving, watching people drink and dance at a party, and my mind exploding with the thought: omg they’re just PEOPLE. They’re just regular-ass PEOPLE!! And this country is just a fucking PLACE!! I don’t know what exactly I had been expecting (another planet?), but I remember visceral waves of shock running through me as I kept thinking: do other people know this??


After that experience, it was years before I had the opportunity to travel again. When it happened again though, my mind was just as blown.


My best friend’s family took me with them on family trips, like to Montana, where I learned to snowboard, and to Tanzania, where we did an incredible multi-week safari tour. These trips continued to expand my horizons, and as I met new people, learned new things, and saw new places, I discovered the glorious high that I get when my brain is in see-new-shit mode, instead of day-to-day mode.


Did you know this is actually a thing??


Our brains are more interested in our survival than our happiness, so when we’re in environments we know well, it kind of just… ignores a whole bunch of shit. When we’re in environments we don’t know, however, our brains are like “ok pay attention to everything, because we don’t know what’s important or relevant yet!”


This is why traveling forces us to be present in the moment, and pay closer attention. It invites a more curious, open, and attentive mindset, and it leads to far more interesting experiences and sharper memories.


Personally, this mental state is my absolute favorite. I love the sharpness, the creativity, the openness, and the ability to be present that traveling brings out in me, and I love how much I learn about myself (and the world) every time I do it.


This, above all else, was why I started to think about shifting my business online 10 years ago. I loved the decade I spent living in NYC, and I loved being a personal trainer, but I wanted the logistical and economic freedom to travel.


When I did leave NYC, I spent some time staying with friends and family in different cities across the U.S., and then I booked a ticket to spend a few weeks alone in Costa Rica.


Quepos, Puntarenas Province, Costa Rica
Quepos, Puntarenas Province, Costa Rica

I chose Costa Rica because nine years in NYC had left me with a serious vitamin D deficiency, and I desperately wanted sun, warmth, sand, and ocean air.


Strangely enough, several acquaintances from the fitness industry were there too, so after my peaceful 2 weeks in a surf town alone, I took a bus across Costa Rica to spend a few weeks with them. It ended up being such an incredible experience that I eventually got my own place nearby, and stayed a total of 3 months.


I learned so much from this crew about how to run a business online. (Jon Goodman was running the already-successful PTDS, and Molly Galbraith was running the already-successful Girls Gone Strong.) It was in Costa Rica that I created, launched, and ran my first content-based program online. I also learned that I hate surfing, love tanning naked, and I require a network of peer support to thrive.


Next up, I booked a ticket to spend three months alone in Thailand.


Chiang Mai, Thailand
Chiang Mai, Thailand

Other than my plane ticket, all I booked in advance for that trip was four nights at a hotel. With my newfound confidence in my ability to figure shit out on the fly, I trusted myself to wing it. (By the way, winging it is a skill I cannot recommend cultivating enough, as it builds a seriously strong sense of confidence in oneself).


I chose Thailand because it was unbelievably affordable, and because its affordability made it a popular hub for digital nomads, which meant I would be surrounded by like-minded peer support. I was also dying to be immersed in a totally different culture again.


Because of the digital nomad culture in Chiang Mai, I made friends and connected with people from all over the world. Every coffee shop in town was filled with people from Australia, Denmark, Canada, Germany, Israel, the UK, Greece, the Czech Republic and other folks on computers, happy to share about their own online businesses, and eager to hear about mine.


Fun fact: it was in Thailand that I discovered Republicans don’t travel!


They may take “vacations,” but you’ll almost never find a young Republican living in a hostel for months on end, backpacking around Europe, immersing themselves in a new culture, or living on a shoestring budget just to see the world. (If you’re a Republican who has done this tho, hit reply! I’d love to hear from you!)


Anyway, I just kept going from there, spending months alone in Portugal (my favorite place ever to just walk aimlessly), along with time spent in Peru, Hawaii, and Puerto Rico in different ways. And I’m thrilled to now be here in Greece, with see-new-shit mode activated.


Are you a lover of travel, too?


If so, feel free to hit reply and tell me your favorite place you’ve ever been! Big hug from Santorini, Jessi

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