On the (metaphorical) Road Again

Some thoughts on travel and the value of feeling uncomfortable

Mike Raab
The Raabit Hole
Published in
7 min readDec 15, 2021


Riding the Metro Cable up to Parque Arvi in Medellin

Well, I’m back at it. Once again, backpacking solo through multiple cities and countries. This time it’s just a short jaunt in comparison to my last trip — 3 weeks through South America instead of 3 months in Europe. But it is funny how quickly things come back; feelings you haven’t had since the last time and maybe forgot about.

When you set out on a trip, your ambition is to be adventurous! To wander upon the hole-in-the-wall in the alley that is better than anything you’ve ever tasted with charmingly authentic atmosphere.

But, at least at the beginning of a trip to a foreign land, a need arises… the need to feel safe and get your bearings.

In my daily life, I have zero fear about my physical safety or well-being. And while I also know that for the most part I am very safe while traveling (partially because of my cautiousness and intentionality), when you suddenly do have people approaching you on the street that won’t leave you alone — clearly having identified you as someone they can take advantage of — it activates a certain awareness and stress system that ultimately seeks reprieve, even at the expense of finding that hole-in-the-wall you had desired to wander upon.

I learned during my first backpacking trip to look like a mess. When I first started out, clean-cut and clean-shaven, I was approached often. As time went on and I looked increasingly scruffy, the interactions diminished. Maybe I had actually learned how to project my unlikelihood of being a fruitful target; but I think the unkemptness was definitely a factor.

So, I brought that intentional unkemptness into this trip (albeit not as extreme as 3 months without shaving.) The intention to look like a disheveled, dirty, nobody. Call me weird, but I find something deeply romantic about this. As I sit sweating in a hostel room in Cartagena, itchy beard, hair sticking up everywhere, re-reading “Man’s Search for Meaning” as foreign music resonates from the lobby through the walls. It wouldn’t make sense to be clean-cut and well-put together here. And I wouldn’t want to be.

Who’s going to think the guy wearing these shoes has anything worth stealing?

Perhaps it’s the influence of literature, or of Anthony Bourdain and the like. But the discomfort is ultimately a benefit. Or maybe it’s the story, which I may be proving by writing this. But the point is, I don’t travel to new places to feel safe and stay in 5-star accommodations shielded from the reality of a city. I travel, first of all — because I’m curious, and want to know a place. What it’s like. I want to be able to relate. To find the humanity of it. But I also travel because it’s a challenge that makes me uncomfortable in a way I don’t feel at home. It’s not easy. I’ve relatively figured out daily life in my “real-life,” at least to the point where I don’t have to be uncomfortable if I don’t want to. As someone who believes it’s important to face discomfort to expand our comfort zones and avoid stasis or contentment, these trips are the best way I know how to get a large dose in a short amount of time.

When you first start a backpacking trip by yourself, your guard is up and you are anything but comfortable. You don’t have your bearings. You don’t know what to expect, no matter what you’ve read online.. You don’t know how to react to what happens to you.

Pretty quickly, something magical happens — you learn, adapt, adjust. To me, there’s a grand feeling of accomplishment after arriving in a new place with a new culture and currency and language you don’t speak fluently, and ~36 hours later confidently navigating it without the aid of a phone or map — waking up, knowing the area you want to investigate for breakfast, knowing what to expect to pay, and walking back to home base without any need for directions. Yesterday it was foreign — today it is familiar.

Maybe it’s my version of “conquering” a city, but in reality it’s just becoming comfortable as a solo traveler in a new one. I should probably preface — I don’t like to do too much planning ahead on solo backpacking trips. There’s something too touristy about planning for me. My favorite move is to show up to a new place, wander around for a day, and then double-back to what I found interesting.

I’m also a huge fan of the Free Walking Tour movement, and on the FWT of Cartagena my guide Elise would repeat a phrase. Something like: “If you want to be comfortable and pay with your card, you can go to this area. If you want to be authentic and see the local crowds, you can go to this area.”

This phrasing, at first, made me feel shameful and guilty that I wanted to sit outside at a table in a beautiful square and eat good food and have the convenience of using a card instead of counting out paper currency, which — it felt she was implying, was touristy and betraying the authenticity of her city. I know she didn’t mean this, but it was my interpretation.

Can’t I do both? See the authenticity and enjoy the comforts? Does it make me a bad traveler to give business to the beautiful ambiance of an upscale establishment instead of the street cart vendor? I genuinely worry about these things. I don’t want to contribute to wealth inequality in the places in the world that are generous enough to host me as a Curious World Citizen.

It reminds me of a piece I wrote a few years ago, “What to Appreciate Before you’re Rich & Famous,” where I opined:

When your financial fortune rises, your standard of living likely does as well. As you dine at more expensive restaurants, travel in first-class, and surround yourself with the highest quality material goods — you’ll likely get used to a certain level of service and quality. Whenever these expectations aren’t met, frustration or annoyance may arise.

Part of me fears that my standard of living has risen too high, and that my “comfort” is more of a baseline expectation than a need.

Perhaps there’s another layer to this all — as someone who has lived alone since pre-pandemic times, through “quarantine” for the past ~2 years, I have noticed an increase in anxiety around crowds. Add in that I’m a foreigner speaking a foreign language in these crowds, and it doesn’t seem so crazy that finding a nice, quiet, comfortable spot to sit and have a beer is alluring.

One of the fun things for me about traveling is the feeling of accomplishment once you get comfortable and confident. There’s an awful lot of anxiety when you’re trying to navigate an airport to catch your international flight from one foreign country to another — but when you do so, with relative ease and little trouble, you get an immediate confidence boost. The kind that doesn’t come from everyday life, but from doing something alone that no one else even knows about. Sure — you’re thinking “going through an airport isn’t an accomplishment, Mike.” And I agree at the surface. But, if you haven’t traveled solo through unknown circumstances with surprises popping up — like the Uber driver at the Medellin airport directing you in Spanish to walk far away from the scheduled meeting spot because the taxi drivers don’t like Ubers… let me tell you that sometimes the simplest things still feel big.

I have a pep in my step in Medellin. I caught myself laughing randomly a few times yesterday, realizing how fortunate and grateful I am to be able to do this — travel as a Curious World Citizen to see what life is like in different places; both what’s novel and different, but also what’s strikingly similar. Walking in the Poblado neighborhood last night, full of greenery in the 70 degree evening air, “It’s a Monday night,” I thought, laughing that I could be in Medellin on any given Monday. I laughed again on the 4th floor of a shopping mall eating a traditional Colombian meal of Bandeja Paisa, thinking how I’d never eat at a mall in the USA. When in Rome.

So on day 4 of this 22 day trip, I’m in high spirits, feeling energized and reinvigorated that there’s so much to see and experience in the world. I’m already more confident in myself. There’s just this exhilarating feeling when you feel confident to navigate traveling by yourself in a foreign land. Even more so when you feel like you’ve gained the respect of the locals — not honking at you like they do to other tourists, responding to you in their language because your attempt to speak it was good enough for them to assume you can. I guess what I’m describing is the feeling of belonging. Or maybe not belonging — but not being an outsider. When I can show up somewhere and within 24 hours not feel like an outsider, it makes me feel so human and connected. We have so much in common, and I love discovering that around the world.