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  • Writer's pictureDillan Taylor

South America, Ep. II: Return of the Gringo



I just finished my first full day in Medellín, a popular travel destination in Colombia. It's just a few hours away from Bogota, the capital city.



My spring was spent in Buenos Aires, Argentina. I fell in love with the city and a Brazilian woman.


People there told me I'd make traveling friends and then meet up with them in different countries. I thought they were crazy...



Until I met up with my two close buddies here from Buenos Aires. They picked me up from the airport. Then we worked out, took ice baths, and went out to a football match and then to watch the UFC fights.


The plan this year was to live it up in South America, then spend the summer in the States to focus on family and work, then click the "play" button again and continue my adventures.


Here we are.


The summer months flew by. I connected deeply with relatives I didn't grow up with. I made significant strides in my 1-on-1 coaching business. And I started a new company: a coaching agency for content creators.


Now I'm sitting in my Colombian mountain home, the sun shining down on my face, typing away. Aside from the occasional tropical rain, the weather here is typically 70 degrees with zero clouds in the sky.


There will be much to share going forward. But I want to briefly throw out three lessons that struck me when I got here this weekend.


1) Just buy the plane ticket.


I bought my flight to Medellín the day I got back from Argentina in May. For two reasons...

  1. I didn't want to risk me coming up with excuses not to return.

  2. I wanted a clear deadline to base my summer around.

I got into a flow state with work between May and August. It would've been too easy for me to put off traveling.


We humans are fantastic at coming up with reasons to not do what we really want.


Also, it's so much easier to just have the plan set in stone on the calendar. That made it effortless for me to organize my work, my finances, and the rest of my world around the simple fact: I'm getting on a plane to Colombia on September 8th at 3:40 pm.


2) The scary becomes simple.


My plan was to get here Friday night. But that didn't happen.


I got off my connecting flight in Bogota, turned the corner, and saw no signs for "Domestic Connections." Naturally, I headed toward the next best option: "International Connections."


I asked the woman at the info desk about my flight to Medellín. She told me I had to go through customs first.


Looking left, I asked, "You mean that giant line pouring out into the main hallway?"


"Si," she affirmed. "What time is your next flight, sir?" I looked at my Apple watch.


"11 minutes."


I have a history of intense travel anxiety.


I missed a simple flight to Vancouver. I got off the bus at the wrong city in Bavaria. Each event like this pains me because deep down I have this fear that I'm incredibly stupid and should never be left alone.


What I've learned this year though, is that if you do even a moderate amount of traveling or get on more than five planes...something is bound to go wrong.


I had a short layover. I didn't realize I'd have to go through immigration...That's really it.


I called my girlfriend to tell her I would miss my flight. I heard her typing as she immediately began scoping for my best options.


There were none.


Expecting me to be my usual anxious self, she reassured me that everything would be okay.


"I know," I replied. "I'm so excited to be here! I'll just stay a night in Bogota."


I was at peace. I thought, I've been here before. Exposing yourself to the unfamiliar and sporadic strengthens a lot of mental muscles.


With her help, we found a hostel—the same company as the one we met at in Buenos Aires. I booked a room and ordered an Uber.


Jiujitsu. Entrepreneurship. South America...


There were distinct times when I remember not feeling welcome or comfortable in these spaces. But now they all feel like home.


And the only way to get to that feeling is to keep stepping into the cold and dark unknown. It doesn't take long for it to lighten up and become warm and cozy.


3) Minimalism is the shit.


Here's everything I brought to Colombia...




It took me 11 minutes to unpack. No checked bags. Just two heavy backpacks.


Granted, the weather here doesn't call for sweaters or pants. But the insight is still the same.


Traveling exposes how little we actually need. I'll wear the same outfits each week, and no one will ever notice.


Aside from the logistical relief, it also just makes me feel clearer mentally. When you don't own many things, it's physically impossible for your space to get cluttered. It also makes me treasure the few items I do have.


Anyway, I'm thrilled to be here.


My friend from the States asked me what it's like to be traveling again.


I responded, "I feel like myself again."


It's good to be back. See you next week.

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