I'm currently in Tulum, Mexico, reviewing photos from the weekend and this one in particular reminds me of a lightbulb moment I had, which caused me to begin my Digital Nomad life:
Let me explain:
It was December 2015; I had reluctantly left behind my expat life in Thailand and was living at home in Boston for four months, working a contract job while trying to decide which one of two job offers I wanted to accept (best problem ever, I know). One job was a full time remote position with the startup company I was already working for, and the other was a cool position at a digital marketing agency in Malta.
My thought process at the time, while watching the snow fall in Boston, was that while I DID think working remotely would be cool, I was worried about not having structure or a social circle of colleagues in my day to day. If I were to work remotely, I had decided that meant returning to my old life in NYC (which I loved, but is still just as expensive as ever), but taking lots of long weekend trips and visiting my family often.
With the Malta opportunity, I’d get my “expat life” back (which I REALLY loved), I’d have structure and colleagues, plus the country has year-round beautiful weather (I’m a huge baby about the cold), and I had always dreamed of living in Europe. So guess which one I chose?
Maybe you guessed it: I accepted the position in Malta, which would start in February, and I told the other company I would continue my contract work with them for another two months until I went to Malta. I was hesitant about Malta because it’s a small island and I was very used to big-city life at the time, but Malta checked more boxes and seemed a lot safer of an option.
Going to Malta meant I’d have two months to kill at home. Since I’m always looking at flights when I’m bored, I noticed there was a cheap one to Costa Rica over the New Year and I booked a last minute trip there with my friend 
Flash forward: I’m sitting in front of beach, next to a beautiful pool on a lounge chair in Costa Rica... with my laptop... making money... getting paid(!?)... Wait... What have I done?? I could go work from NYC and spend all my money on rent and coffee shops, or I could stay in less expensive countries like Costa Rica and use some of that leftover money for more flights, and still have some left over. I could go home whenever I want... I’m FREE.
It’s worth noting that I had never heard the phrase digital nomad before, and honestly had never considered traveling and working at the same time because it simply hadn’t dawned on me that I could do that. When I realized though, I called both companies and reversed my decision (it was a hard conversation with the Malta company, which I still feel guilty about, and luckily the offer still stood with my current company). I cancelled my return flight home and I stayed. I met some people who invited me to join them in Nicaragua, so I went. I moved on to Colombia, where my mom visited me and brought me more clothes so I could survive outside of central America. I hopped over from there to Ecuador, because it was right next door, so why not? And I flew over to Brazil because I found a cheap flight and it was on my bucket list.
Six months after I had my lightbulb moment I was back home with much more money, stories, language skills, and overall life experience than I had left with. Three years and 44 countries later, I'm still doing it here in Tulum, and loving every minute!
