Chapter 29: Reflection.

115 days abroad. 10 back home. Time to reflect.

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115 days.

Thousands of photos.

19 countries.

16 flights.

10 ways to say “cheers”.

And dozens of incredible people that I now call “friend”.

What a trip. Reflection is important, and there is no better time to reflect than at the end of the year. Let’s begin.


There’s what it looks like, and then what it is. This wasn’t a spur of the moment thing. Honestly, it was one of the more calculated decisions of my life. But to understand this whole thing, you need to know a little bit about me and how I look at the world right now.

Let’s go back one year, to December 2020.

I was 23 years old, I was working in corporate finance for UPS, and thus far, I had done everything that you were supposed to do to “win” at life.

  • 4.0 GPA with both a Spanish and finance degree? ✅

  • Fraternity president and football captain? ✅

  • Accepted to top five MBA program? ✅

  • Great job in finance sector? ✅

And for the cherry on top, I was really freaking good at trading stocks. 5000% in a year. Not bad. What was coming next? Probably get a promotion at work. Get an MBA from Columbia. Go work for McKinsey & Co. Pivot to a C-suite role with a Fortune 500 company. Work my way up to CEO.

Jack Raines, living the American Dream.

Up until that point, I hadn’t thought a ton about why I was doing… anything. I was just doing what I was supposed to.

My decision-making matrix was simple: Will this help me “advance” my career? And life was becoming a never-ending pursuit of the next level up.

I didn’t really care for my job all that much. But I knew that I would be going to Columbia Business School in August 2022. So I was coasting until then. And I was just staring at screens day in and day out. Making Excel files. Trading stocks. It was Groundhog Day.

And the entirety of 2020 was one big blur in my apartment. Days, weeks, months. A year of my life gone in the blink of an eye. And I was just staring at screens. You can probably relate.

Then one day, I woke up from this American Dream. It was like my mind was screaming, “What are you doing with your life?" And it scared the shit out of me. All of a sudden, I became acutely aware of… everything. How fast time was going by. How I was spending my time so poorly. “Working” eight hours a day, five days a week. Wishing away Monday - Thursday, so the weekend would hurry up.

“Is this really how you want to spend the next 40 years? Just grinding your way up the corporate ladder doing stuff you don’t care all that much about, to maybe retire and try to cram in some fun at the tail end of your life?”

Here’s a few quotes from my first Backpackin’ article back in August, describing how I felt at the time:

It was like a switch flipped in my brain.

I can literally do whatever I want. So why am I doing what I’m doing every day?

I think a lot of people are stuck in a similar cycle. When you hit that “Oh Shit” moment, you have two options. You can ignore that “Oh Shit” moment, and double down on the job that you hate because a little more money or prestige will certainly solve your problems. Or you can embrace that “Oh Shit” moment and go figure out what you actually want to do with your life.

But you won’t do anything about it unless you become aware of two things:

  1. Your current situation isn’t all that great

  2. Your time is limited

If you’re apathetic about your situation, and/or don’t have a sense of urgency about making changes, you’ll stay in the loop forever. But once you do realize you want a change, and understand that it’s on you to seize the moment, you’ll probably make some immediate course corrections in your life.

I figured that if there was some ridiculous stuff that I wanted to go do, I needed to go do it. For me, that ridiculous stuff was living out of a backpack in another continent for four months. And it was the best four months of my life.

Now that you know where I’m coming from, let me tell you more about my trip.


When I landed in Barcelona on August 25th, I was terrified. I had romanticized this super cool travel idea for over a month, but reality set in once I landed.

Foreign country. Foreign language. Sharing a hostel room with 8 strangers. Would I make friends? My mind was racing at 100 miles an hour.

So I went to the hostel and checked in. And I noticed two dudes playing chess. I overheard one of them say, “Dude that move was sick!” And I knew they were American (because who else would call a chess move sick).

I introduced myself to two guys from Seattle named Tanner and Rylan, and I ended up jumping on a last minute flight with them to Prague a few days later. And that set the tone of my trip. If you’re friendly and take an interest in others, you’ll make friends quickly. And good friends are the key to good travels. And that theme continued over the next four months.

You never know who you will meet in Poland, or Portugal, or Prague. But chances are, you will make friends by being a friend. And when everyone is exploring foreign lands, bonds form quickly.

Four of these bonds led to a group of us, dispersed all over the continent, meeting back up in Venice to roadtrip all over Central Europe. Because when you’re on the other side of the world, a two week friendship is practically a lifetime.


I’m a 24 year old white dude from Georgia. Which means that I view the world as a 24 year old white dude from Georgia. Capitalism is king. College sports are awesome. Meritocracy rewards winners. I brought a Mike Vick Falcon’s jersey with me for NFL Sundays. A well-rounded American.

And my first roommate in Barcelona was a 20-something German guy named Jules. A self-proclaimed democratic socialist. He believed billionaires are a flaw, not a feature. Capitalism relies on exploitation. Football is a game where you kick a ball into a net.

Jules also looks like McLovin.

So we were polar opposites. And rooming with him was the best thing that could have happened to me, because we got to talk about all sorts of stuff. And we didn’t agree on anything. But it did show me that people’s beliefs are largely a function of their backgrounds. 

If you want to understand why someone’s beliefs contrast yours, ask yourself, “Where did they come from? What’s their story?” And you might realize their ideas aren’t quite as strange as you thought.

Over four months I met all sorts of people with a variety of opinions and beliefs. And I learned something from all of them, whether or not I agreed with them, because they taught me so much about where they came from.

A caveat. There was one person that I didn’t learn anything from. I actually think the interaction made my brain smoother. There was this anti-vax Croatian girl who thought that Tanner actually got the mark of the beast from Pfizer and Mark was a Navajo tribe member named “Little Foot”on a spirit journey in Europe. If I learned anything, it was how far the left tail of an IQ bell curve can go.

You want to have your biases questioned? Experience some narrative violations first hand? Get out of your country for a few months. A lot of people are living a whole lot differently than us.

“Finding Yourself”

First of all, that’s a stupid cliche phrase. No one “finds themselves” in Europe. Or South America. Or anywhere else. You can’t run away from yourself in a foreign land, and you certainly won’t find yourself there either. Sorry to all of the college students who thought it would make a good caption after a semester in Italy.

That being said, getting out of your home country does help you separate “you” from your environment.

See, when you’re living out of a backpack in Europe for a few months, you leave 99% of your material possessions behind. You don’t see your friends and family from back home. You break free from your routine activities. You’re a blank slate in a new land.

The stuff that you still do. That you still care about. That you still think about. That you still long for. That’s “You”. You’ll notice a lot of stuff that you used to do, or think about, or care about no longer matters.

That’s the stuff that you thought was “you”, but it was actually your environment impacting “you”. We all do things to fit in. Anything that remains when fitting in no longer matters is likely core to your being.

For me, one of the biggest things was writing. It would have been easy to just screw off for four months without writing a word over there. But I felt almost compelled to write everything that I could, every day. So here I am back in the States, writing everything that I can, every day.


You would be shocked by how quickly you can adapt to pretty much any situation. By day five, living out of a backpack felt normal. Sharing a room with 8 strangers felt normal. Going out on little adventures felt normal. You can settle into a routine of literally anything. And this leads to some funny phone conversations with friends and family back home.

“What are you doing today?”

“Oh you know, working. Been on calls all day. You?”

“Went dogsledding this morning, probably about to work out.”



If you have been thinking about making a major life change, but you don’t know how you’ll adapt, just do it. We are literally built to adapt. And that urge isn’t going to go away.

Doing What You’re “Supposed to Do” Is Overrated

This is honestly my life motto at this point. There are so many cool places to visit. And cool people to meet. And cool foods to eat. And cool hobbies to try. And cool ways to make money. (Yes, you can actually make money doing stuff that isn’t “normal”.

Yet we’re so focused on the corporate ladder, that we don’t see all of the other ladders available.

Your life doesn’t have some predetermined storyline. It’s an open world, and you can do whatever you want. Spend time exploring. Visiting new places. Meeting new people. Trying new hobbies. Go do some of the side quests. Let a side quest become a main quest. Why not?

No one is going to be impressed by how well you followed the rules. A lot of people will be impressed by how well you disregarded them.

Opportunity Cost Is Everything

Productivity consultant David Allen once said, “You can do anything, but not everything.” That’s the damn truth. I had never really thought about that until I went to Europe. This is most definitely a first-world problem, but I was overwhelmed by choice. When you can get anywhere within three hours, how the hell do you decide where to go? Because you can’t see every part of Europe in a few months. And if you try to, you won’t stay anywhere long enough to actually experience it.

And that’s life. A decision to do anything is inherently a decision not to do some other thing.

Choosing one career path is not choosing 100 others.

Choosing a partner is not choosing a billion others.

100 hours spent working this week is time not spent with friends and family.

We all face these choices every day, and the choices we make shape our lives. However, not making a choice is, in itself, a choice too. Choosing not to do anything because you don’t know the right path is the worst choice of all, because your opportunity cost becomes everything. The longer you spend “undecided”, the more that cost grows.

Choose wisely, but choose quickly.

Small Activities Compound

I started writing before I left for Europe. I wrote even more while I was in Europe, and a few people read my stuff. Maybe one or two people would subscribe after I published something. Then a few more. And a few more. Then one day, 20,000 people read something that I wrote.

All of those writings that “no one read”? Well a few people did. And those “few people” add up. Because every person that reads it might share it. And every person that shares it exposes their network to my work. And someone in their network might like it. And the more I publish, the more opportunities I have to put my work in front of the right people. And sooner or later, something hits.

Rinse, repeat.

That isn’t just a writing thing. It’s an anything thing. If you can remain disciplined enough to pursue an activity at a steady rate over an extended period of time, your work will compound. And the likelihood of success will increase. Until success becomes probable, not possible.

The problem is, we live in a world obsessed with “now”. So when results aren’t immediate, we become frustrated. And we quit.

Here is an article that I wrote in September.

Here is an article that I wrote in December.

Keep going.

Now What?

Well that’s a great question. I’m pretty sure that I have talked myself out of ever working a regular job again. Which means that I will have to make money doing things that aren’t regular jobs. And I don’t wanna trade stocks again. Luckily, the meme business is doing well in the year of our Lord 2021.

I also have the travel bug. Bad. So I think I’m going to South America in a month or so. I hear Buenos Aires is nice.

I’m going to publish a couple of more updates on here before I’m done. But I have no idea if I’ll keep writing on Backpackin’ when the travels resume. I’m about to be a busy dude, and these things take a while to write lol.

And We Out

If you made it through to the end of this, thank you. And if you have been around since August, a massive thank you. This trip was the coolest experience of my life, and I’m glad I could share it with you.

If you want to take a trip of your own, don’t hesitate to reach out. Email me at [email protected] or message me on Twitter.

Til next time.