✈️ Lessons on Long-term Travel After 6 Weeks in Colombia
Plus a little story on my Gap Year rejection, two quotes, and a few content recommendations
Hi friends 👋
Welcome to the 14 new subscribers since my last Baer Necessities newsletter in February. In this newsletter, I share my thoughts and stories on long-term travel, freelance marketing, tech trends, and living a good life — only the Necessities.
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In today’s email:
My lessons from Colombia and long-term travel + a gap year rejection story
2 quotes I’m thinking about from Alan Watts and Terry Pratchett
3 pieces of content I’m learning from (1 essay, 1 book, 1 podcast)
Let’s get to it!
“If you decide to take a break right after high school you are forfeiting your scholarships and admission to the university. You will have to reapply next year for Fall 2016.”
My university admissions department sent me this in an email on January 15, 2015.
And with that, my dreams of a Gap Year to travel the world after high school were shattered. Of course, this was a first-world problem, but I was still quite upset.
You see, I was just accepted into one of my top college choices with a pretty decent scholarship.
This should have been an exciting and proud moment after four years of hard work and preparation, right?
But deep down, what I really wanted was to travel the world and take a step back from the career-oriented hamster wheel.
I had a friend who did a Gap Year in Israel a couple years earlier and was very inspired to do something similar (side note — this friend is actually my sister’s fianceé now, huge mazel tov to Leah and Josh!).
For my Gap Year, I wanted to learn more about myself and what’s most important to me in a self-structured gap year filled with things like volunteering or working abroad, writing about my travels, cultural immersions, and learning new languages.
But I really couldn’t afford to lose this scholarship and have to reapply the following year.
So I started university that year, completed the typical 4-year track at a big state university, made some of my best friends to this day, and ultimately had the time of my life.
I wouldn’t change a thing.
But as I write this from my co-living space in Medellin, Colombia, where I’ve spent the last few weeks, I can’t help but feel insanely thankful for this opportunity to travel and work now.
It’s crazy how far I’ve come in the last nine years since I wasn’t able to take that Gap Year.
Sometimes, it’s easy to fall into the comparison trap of wondering “WTF am I doing and why don’t I settle down in one city like most of my friends or take a more traditional desk job.”
But then I find myself eating dinner overlooking Medellin with a group of remote workers from across the world and wonder why would I want to be doing anything else right now?
Life is about sacrifices and priorities, and I’m happy to sacrifice a stable life in the States right now for a life traveling the world. This could change in the future, but for now, I wouldn’t want it any other way.
I’m not a religious guy, but I do think everything happens for a reason. And there’s a reason I didn’t go on that gap year way back when.
It was to prepare myself for a different type of slow, long-term travel years later.
Now, nearly six weeks into my trip in Colombia and South America, I wanted to share some of my insights after traveling in this stunning country.
Without further adieu, here are my lessons on long-term travel, Colombia, and remote work:
Lessons on Colombia and Long-Term Travel
Embrace the “boring” moments of travel.
Sure, travel can be adventurous, exciting, and give you the highest of highs.
You can hike to see the tallest palm trees in the world, bike 30 kilometers down a mountain, check out the best miradora, or viewpoint, in town, eat world-class meals, hike a big rock overlooking Guatape, check out cool museums, or do the next walking tour.
But for me, when I think back on my trip so far (or any of my previous trips), it’s not about the big, exciting things or the Instagram-worthy pictures. It’s about the seemingly boring, mundane moments.
Like getting coffee and a sweet snack from your Airbnb host in a small mountain town every morning. Or talking with the Venezuelan immigrant who runs the best empanada stand in the town. Or learning from my U.S. expat neighbor who visited Salento for a few days and decided to stay for a few years. Or the backpackers you meet in hostels with countless different stories or the friends you make while hiking “solo” or the receptionist at the hostel or the digital nomads you meet in your coliving space. You get the point.
It really is about the people and ideas you’re exposed to along the way, not the places you go (as cliche as it sounds). Pay attention to the mundane.Colombia is safe (as long as you use common sense).
Colombia gets a bad rap of being a really dangerous country. If you think it’s a 10/10 in terms of danger, it’s more like a 2 or 3 out of 10 these days. But like everywhere else in the world, if it bleeds, it reads, and you only see the negative sides of a country in the news. I’ve never felt unsafe in Colombia and many times, I have felt more unsafe in my hometown of Memphis than I do in Medellin.
The same rules apply here as other developing countries. Don’t walk around with your phone hanging out of your pocket, pay attention to where you’re going, and stay in the more tourist-friendly zones, and you will be fine. Use your head.Bogota is underrated.
A lot of what I learned before I came here was that Bogota was boring, unsafe, and not worth more than a day or two of your trip there. But after spending 12 days in Bogota, I found myself really loving the city!
The beautiful old town called La Candelaria is an amazing place to base yourself with so many good cafes, historic sites, and great restaurants a short walk away, some that only cost you $3 USD for an authentic Colombian meal. There’s incredible viewpoints, hikes nearby, and the mild weather is really pleasant as you’re pretty high up in altitude there (though many Colombians from elsewhere will tell you it’s too cold). My one complaint is that there’s not much greenery throughout the city and, at least for me, I found I needed to escape to nature after a week or so there.Medellin lives up to the hype.
I’ve now been in Medellin for almost 3 weeks now and love this city. I heard so much about Medellin before coming here, mostly incredible things, but I was a bit skeptical.
After seeing it for myself, I can see why so many nomads decide to base themselves here for a while. It really is the “Land of Eternal Spring,” as they call Medellin, with trees and plants everywhere, views of the mountains from all angles, and great hikes within 10 to 15 minutes of where you would be staying. There’s an amazing community of remote workers, a good local tech scene, a big focus on healthy living, and the night life isn’t too bad either. I’m leaving for the Colombian coast to Santa Marta in a week, but I don’t think this will be my last time in Medellin.Don’t plan too much – leave your itinerary open for the unexpected.
Of course, do your research and come in with a rough idea of what you want to do and see. But if you’re like me and want to optimize for flexibility, don’t book your flights or bus tickets too early to allow for serendipitous plans to unfold.
For example, I had never heard of this small mountain town called Salento before coming here, but after meeting countless backpackers in Bogota who had gone there (or were going soon), I decided to take an overnight bus to Salento before Medellin. I loved it so much that I ended up spending 9 days there when I originally planned to go for 3 or 4 days. The nature and views there are unmatched and the locals were so nice too. I have so many other stories like this playing out in my favor from previous trip… but if you’re the kind of traveler who likes to plan everything to the tee, then this suggestion probably makes your skin crawl.Your environment matters a lot while working and traveling.
If you’re working remote and traveling, try staying in co-living spaces with other remote workers or find a way to build a community elsewhere in coworking spaces or joining local hobbies or sports. That’s what I’m doing in Medellin (after staying in backpacker hostels my first few weeks) and it’s much more sustainable for me. It’s a great way to meet similar-minded people that aren’t just traveling on holiday for a few weeks and can encourage you to work out and keep a healthy lifestyle while you travel and work.Learn the language.
Local people will respect you way more if you at least try to learn Spanish and speak it with them. Anyways, learning languages is fun when you get to use it after. My recommendation if you want to learn independently in the US: use Pimsleur to get yourself speaking basic conversations as quickly as possible.
And here’s a few more quick lessons:
Don’t drink the tap water in Colombia. Trust me.
If you want to start freelancing, just start. Stop thinking so much about it.
Find a way to incorporate your routine from back home while you travel (work out, meditate, journal, do what you have to do to keep some resemblance of a routine).
Book that one-way flight and don’t look back.
And that’s all for now!
Colombia really does give you the best of all worlds — amazing historical cities, breathtaking mountains, beaches, jungles, deserts. You name it, you can find it here.
Please let me know if you have questions on Colombia or anything I talked about here (or even better, if you have recommendations for me!).

Two Quotes I’m Thinking About
Because who doesn’t love a good quote?
Philosopher Alan Watts on writing well:
“Advice? I don’t have advice. Stop aspiring and start writing. If you’re writing, you’re a writer. Write like you’re a goddamn death row inmate and the governor is out of the country and there’s no chance for a pardon. Write like you’re clinging to the edge of a cliff, white knuckles, on your last breath, and you’ve got just one last thing to say, like you’re a bird flying over us and you can see everything, and please, for God’s sake, tell us something that will save us from ourselves. Take a deep breath and tell us your deepest, darkest secret, so we can wipe our brow and know that we’re not alone. Write like you have a message from the king. Or don’t. Who knows, maybe you’re one of the lucky ones who doesn’t have to.”
Author Terry Pratchett on why we leave home:
“Why do you go away? So that you can come back. So that you can see the place you came from with new eyes and extra colors. And the people there see you differently, too. Coming back to where you started is not the same as never leaving.”
Three Links Worth Sharing
Things I’ve been learning or diving into over the last month.
Essay I’m Reading:
Ambition’s Gravity by Packy McCormick —
If you want to get fired up to work on solving big, ambitious problems, read this short essay. I wanted to run through a brick wall after reading and it’s made me rethink my longterm goals more. My favorite line from the essay:
“I’m here to tell you: you can simply decide to do big things.
And I’m here to argue that you should spend the time to figure out the most ambitious thing you could dream of doing with your one wild and precious life.”
Book I’m Reading:
Magdalena: A River of Dreams: A Story of Colombia by Wade Davis —
I wanted to get my hands on a book about Colombian history and culture while I’m here and this book from Wade Davis hasn’t disappointed. Highly recommend if you’re planning a trip to Colombia or just want to learn about the country! From the book’s description:
“At once an absorbing adventure and an inspiring tale of hope and redemption, Magdalena gives us a rare, kaleidoscopic picture of a nation on the verge of a new period of peace. Braiding together memoir, history, and journalism, Wade Davis tells the story of the country's most magnificent river, and in doing so, tells the epic story of Colombia.”
Podcast I’m Listening to:
How I Write with David Perell —
I’ve binge-listened to this podcast from David Perell, listening to almost every episode over the last few months. If you’re interested in hearing from some of the world’s best writers and operators on their biggest writing tips, you really can’t miss this podcast. Start with these interviews with Shaan Puri, Tim Urban, Tim Ferriss, or Kevin Kelly (but really, all of them are amazing).
If you made it this far, thanks for reading! Feel free to send it to someone who loves Colombia or will be traveling here soon.
It’s so crazy to think we’re 25% through 2024. Let’s make the most of the last 3/4. I hope you have an amazing month of April!
Don’t be a stranger, and reach out whenever.
Until next time,
Jonah Baer
P.S. — Check out my personal site if you want to see more of what I’m up to.