The Timeless Stuff.

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This is an attempt to turn some jumbled feelings into words. We’ll see how it goes.

If you’ve followed me for a while, you probably know that I spent the majority of August 2021 - July 2022 traveling outside of the US. But I’m not here today to tell travel stories, I’m here to talk about what came before the travel stories.

The reasons that I decided to travel for so long were straightforward:

1. I knew I was moving to New York in a year for business school.

2. I was alarmed at how the last 18 months had passed by in a monotonous cycle that lacked novelty.

3. I had enough money that I could afford to quit my job and travel.

4. I was hit with the existential realization that this would be my only chance to spend an extended amount of time traveling, at least while I was young.

Life is nothing if not a never-ending navigation of opportunity costs, and the opportunity cost associated with not taking this leap was immense.

The thing is, while I realized that this would be my only chance to travel for the greater part of a year, I also realized that this would be my last chance to live with my best friends in Atlanta. And that realization weighed heavily on me.

Friends are important because they’re the only family that you choose. When you are born, you have no say over your siblings, parents, grandparents, aunts, uncles, and cousins. But you do get to choose your friends, and if you choose wisely, some of these friends will become family too.

I was fortunate to have a really, really good group of friends in college. Those friendships where your kids will call your friends “Uncle,” because you’re so close that you may as well be brothers. The best type of friendship.

For most people, those friendships scatter around the country after graduation as guys take jobs in different cities. I was much luckier. For me, almost all of the guys that I considered to be family lived in or near Atlanta after school. To make it even better, my best friend, Chase, and I both landed jobs in Atlanta at the same time, and we spent the next 2.5 years living together. But that fun, happy-go-lucky “college friends living together and hanging out every weekend” part of life doesn’t last forever.

Back to my travel dilemma.

Growing up is weird because one day you’re 18 years old doing dumb college things in a dorm room with some guys that you just met, and then you blink and those same guys, now your best friends, are moving away, getting married, and having kids.

And we were about to blink. We knew that realistically this would be our last year living together because I was moving to New York in a year, and he would probably get a place with his then-girlfriend (and now wife).

My reservation before embarking on travels was the other side of that opportunity cost: this might be my only chance to embark on a year of international exploration, but it was also the last time that I would be living with my best friend, only five minutes away from the rest of my friends.

Some of you, while reading this, might think, “Well no shit Jack, that’s how this whole thing works. Everyone grows up eventually.” And you’re right, but simply knowing how something works doesn’t make accepting that reality any easier.

Like Brad Paisley said, “There’s a last time for everything.” And I wasn’t ready for it to end. Not just yet.

So the summer before my travels began, this idea of “this might be the last time for ______” rarely left my mind. “Last time grabbing dinner with these friends.” “Last time going to this party.” “Last time hitting the gym with the roommates.” “Last time ________.”

I was experiencing a mental funeral for the life that I had come to know and love, and the more I tried to embrace it, to hold it, to make it slow down, the faster everything seemed to speed up. Life sometimes has a sick sense of irony, doesn’t it?

But, despite my reservations, I still couldn’t shake that wanderlust, so on August 24th, 2021, filled with a mixture of nostalgia, excitement, and a hint of sadness for the unknown future events I knew I would miss, I headed to the airport with a backpack and a one-way ticket to Spain.

Before I left, I had one stipulation for those I was closest to: we had to stay in touch while I was gone. While I might not be there physically, I still wanted to be as present in their lives as possible. My biggest fear was that distance and time would damage those relationships.

So for the next four months, from Barcelona to Prague to Edinburgh to Budapest, I would take a couple of hours each week to call my friends and chat about everything that I was doing, everything that they were doing, and stuff that our friends were doing. You know, typical dude stuff that would normally be discussed over the poker table, just from thousands of miles away.

In December, I returned home for a few weeks for the holidays (my grandma would have killed me if I missed Christmas), and on the flight back from London I grew a bit nervous. Yeah, my friends were still my friends, but would it be weird coming home after spending nearly half a year abroad?

Not at all.

I walked in my front door around two in the afternoon, and six hours later I was headed to a Christmas party pregame across town. We hadn’t missed a beat. By 11 PM, besides a few travel questions, nothing had changed at all. I was right back at home.

After moving to New York over the summer, I hadn’t seen all of my Georgia friends together until last weekend, when everyone was in Chattanooga for Chase and Caroline’s wedding.

The night before the wedding, Caroline’s father, Eric, showed up at the house where all of the groomsmen were staying, and he brought with him two things:

1. plenty of whiskey

2. his best friend from medical school (also conveniently named Eric)

Over the course of the night, as the drinks grew stronger and the two Erics’s stories grew funnier and funnier, I realized one thing: this stuff is timeless. These two guys, 30 years my senior, brothers forever connected through a chance encounter in their respective careers, were telling stories from their younger days just like we were rehashing our funniest stories from college. And it was awesome.

A couple of years ago, I believed that the only constant in life was change.

Everything was temporary, here for a moment then gone forever.

That belief influenced how I lived my life: I was so worried about not fully “experiencing” the current moment before it disappeared that I treated each day with a Carpe Diem attitude. This idea of, "I have to do this now or I’ll never have the chance to do it again,” ruled everything, and “growing up” terrified me because it signified the end of so many good things in my life.

But I was wrong.

Sure, change is a big part of life, but it is far from the only constant. The bonds forged between close friends and family and the stories behind those bonds are constant, impervious to change. Our shared stories cement those bonds in stone, allowing us to pick up where we left off after three years without missing a beat.

Yeah, circumstances change, people move, marriages happen, kids are born, and nothing last forever. But the good stuff that makes you dread that inevitable change? Those friendships and stories and countless good times? Those are timeless. Nothing can change them.

And change isn’t all bad. After all, our countless life changes just give us more new stories to share when we do reunite.

- Jack

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And PS: Cheers to the newly-wed Westfalls 🥂

Jack's Picks

• Morgan Housel’s latest piece on “Everything You Can’t Have” is a banger.

• David Perell interviewed Danny Miranda on Danny’s podcast two weeks ago (role reversal). Check it out here.

• Tim Urban, the GOAT blogger who writes “Wait But Why” has finally finished his book, and it’s coming out this month. Preorder What’s Our Problem? here.