What I learned from leaving my job, taking the train across the country, and coming back
Early last December, I read about this strategic planning exercise from Larry Summers (here):
The Five Year Exercise
Imagine it’s five years from now and your company is a massive success. You’ve got a fantastic product, you’ve achieved market leadership, and everyone else is trying to catch up. What decisions helped you get there?
Now imagine the same five years have passed, but this time your company is struggling. You failed to live up to your original vision. Your product has stalled. You’re backed into a corner. What choices led to that moment?
During my first week back in New York, I struggled with framing my trip around the country, both for myself and in recounting it to other people. A few days ago, I found this exercise again and realized that the lesson had been in of me the whole time — I just needed the journey to realize it.
Drop it, and go
When I got back from Brazil in the beginning of January, I was antsy. In Rio, I came to peace with my decision to leave my job, but coming home, I didn’t have a great sense for what I wanted to do next. I had rough ideas, like joining another early-stage team or taking on consulting projects, but truthfully, I also had reservations all around. I was mentally a bit all over the place.
In an effort to ground myself, I went to visit my friends Sebastian Beckwith and Ana Dane at their tea shop. On my way over, I read these two essays by Andy Dunn and James Altucher. Andy Dunn talks about the early days of Bonobos — during which he’s pretty much constantly broke and under a ton of financial pressure — and the decisions that led him there. He put out two thoughts, challenges really, that lodged themselves in my brain:
The risk not taken is more dangerous than the risk taken.
If you can’t decide what to do, get on the road. You won’t find the answer. It will find you.
On the other hand, I’m not sure what my first reactions to James Altucher’s post were. A little over a year ago, he threw out most of his stuff and started living in random places. Recently, he decided to put down roots again and take on a lease, so his post shared what he learned from his experience. It was extreme, but really illuminating.
With my head full of these two stories, I went to see Sebastian and Ana, who have spent the better part of the last 20 years exploring the world in search of great teas. They quickly and easily convinced me to pack up and ship out again. (“You won’t have more time when you’re 50. Just do it.”)
I booked an Amtrak rail pass that night.
Just doing it
I didn’t plan much of my trip before I left.
I booked some tickets, messaged a handful of friends, and packed a few t-shirts. Everything else came together on the fly.
Traveling light is great. With only a few options for clothes, my mornings simplified. Unencumbered by rigid plans, I went where my whims took me. Equipped with only a laptop and notebook, I set up shop all over and made space to create.
In retrospect, my trip needed to unfold spontaneously. I’m pretty introspective, so I sometimes talk myself out of doing things. Winging it meant a lot of things, like occasionally not knowing where I was going to sleep until the last minute or how my days were going to go until they went. Once, it even meant wandering around LA until 5:30 in the morning, when I found a yoga studio that was open — then randomly deciding to spend the next ten hours there.
More important than any of that, though, winging it meant that I was on an adventure across the country rather than in my apartment still wondering about it.
First stop: Chicago
My first train ride lasted about 19 hours and took me from New York to Chicago. I had a lot of coffee that day, so I didn’t sleep much along the way.
Shortly after we pulled into Union Station, I jumped into an Uber and found myself sharing a ride and conversation with Troy Henikoff, a Managing Director at MATH Venture Partners and the Managing Director of Techstars Chicago.
Coincidentally, that morning, fourteen of Chicago’s tech leaders were riding around in Ubers offering free fifteen minute mentoring sessions. I requested a ride with no expectations and was legitimately shocked when a car pulled up and Troy invited me to hop in.
We covered a lot of topics very quickly, from his love of New Zealand and passion for developing the next generation of entrepreneurs to my newfound obsession with Wait But Why and current quest for perspective. Turns out, we both also really enjoy biking as a mode of transportation, even in the cold.
At the end of our ride, he left me with two pieces of advice: 1) Get and read Adam Grant’s Give & Take, and 2) Longer time horizons allow for better decision-making. Gratefully, I noted both, then hopped out and immediately went to pass out on my friends’ couch.
From there, I looped around the country, stopping in New Orleans, Tucson, Los Angeles, and San Francisco and passing through Houston, San Antonio, El Paso, Denver, and Omaha before returning to Chicago and, finally, New York.
I flew a few legs: Chicago to New Orleans, Los Angeles to San Francisco, and Chicago to New York. The rest of the trip happened by train. Unsurprisingly, many routes had poor cell coverage and cross country trains don’t wifi yet, so I spent most of my time — about 126 hours — sitting, sightseeing, reading, writing, and reflecting.
Somewhere in the Southwest, I suddenly realized that time felt different. The feeling threw me back to Brazil — moments danced by, slowed down, then sped back up, but I never lost track of hours. Without access to the outside world, I had no distractions tugging at my attention. Every action became a conscious choice. Limited to what existed within the train, I started to understand how little I needed and what little I truly wanted to focus on.
When we got to Tucson, I spent my hours rigorously shedding all of the things that stopped me from being mentally, physically, and emotionally present. A lot of that time went to unsubscribing from everything in my inbox. The rest of it went to appreciating just breathing and being.
A minute is a minute, but having agency in how you spend it is incredibly powerful.
(I’ve since re-added myself to a handful of newsletters.)
Connecting the dots
Throughout my trip, I was constantly amazed by how interconnected everything and everyone is. We talk about this a lot in many contexts, but it was incredible to unpack firsthand.
For example, it turns out that Troy Henikoff is also my best friend Matt Weiss’s entrepreneurship professor at Kellogg. His class, which only runs once a week for five weeks, happened to meet the day after our Uber encounter. Matt and Troy figured this out, and I found myself in Evanston the next morning for a lecture on SEO.
These coincidences came up everywhere.
Just before class started, I found myself sitting behind Libby Koerbel, a friend of Matt’s whom I met once a year earlier. Unprompted, she connected me to her mom, Jane, who offered to host me in her home in Denver, one of the cities that I hoped to visit.
In New Orleans, I stayed with Marion Martin, a teacher I’d met just weeks before on the beach in Copacabana. Wanting to go swim, my friends and I asked her in broken Portuguese if she would watch our things. When we returned, she was also with friends, one of whom was my neighbor in Brooklyn. Another shared a boss at the UN with my roommate in Brazil.
When I got to San Francisco, I went to a pop-up dinner where my friend Jason Marder sat me with our classmate Felicity Yost. Overhearing my interest in helping early-stage companies grow, Felicity pointed me to her friend Sara Cullen, who was working in VC in New York, to learn more. Weeks later, as Sara and I sat down to coffee, we realized that we’d texted once a year earlier to exchange tickets to a Moon Boots show at Output. Another time, she attended a party at my apartment while I was out of town.
Setting out on this trip, I never expected any of these things to come up. On the surface, every one of us seemed like such different people leading such different lives, but in actuality, we had so many bridges between us just waiting to be uncovered. Finding these connection points led me to the places where we really did differ, giving me access to varied perspectives and approaches to life that I might not have otherwise encountered.
Eating the dog food
I’m lifting the title of this section straight from Chris Deutsch, who sat down with me for breakfast and lunch during my second stop in Chicago.
When I packed up my bags and headed to Penn Station, I didn’t know what I was looking for, much less what I might find. I ended up finding a lot more than I ever imagined.
It’s hard for me, even now, to say that my trip was life-changing because so many things, now that I’m back in New York, feel familiar. But, in many ways, it was. While I was on the road, I grew and learned, and my perspective on life expanded. The last piece, at least, counts for a lot.
In California, my halfway point, I found this line in a Medium post by Geoff Teehan, and it so perfectly described how I felt: “I didn’t change — I sloughed off the things that changed me, and it revealed more of what makes me who I am.” One of the most amazing things about travel is that it forces you out of your routine and, in that, you find opportunities to reevaluate your truths and examine them in new contexts.
For me, that meant taking a step back, looking at my motivations, and doing the homework to figure out what really matters to me. Without the influence of other peoples’ expectations, what do I want for my life? I don’t have all of the answers yet, but here’s what I know so far:
- People matter. Being with my friends makes me happy. Making new friends makes me happy. Connecting people makes me really happy. Hearing everyone’s stories, sharing delicious food, getting into mischief, staying up late to debate ideas, wandering around together, and just generally hanging out is awesome and real, and I’ll always have and cherish those memories. They’re now a part of my story.
- Things don’t matter that much. Obviously, I have basic needs: clothes, food, shelter, etc. But now, I realize how happy I was having just a fraction of the things I own. This morning, I spent 20 minutes rummaging through my sweaters before picking the one I wanted to wear for the day. Did it matter? Not really. Any other one would have been fine. I’d rather have the time back.
- Money matters, but also not that much. Interestingly, I’ve never thought about my “number,” so it was always just some nebulous large question mark that floated around and occasionally gave me grief. Thinking about it was actually really liberating. It reaffirmed that I don’t need much to be happy. I like to travel, I like to see my friends and family, and I like to eat out sometimes — I don’t need extravagance. Recognizing that helped me say no to bunch of opportunities that just weren’t the right fit for me when I got back.
- Travel is important. Actually, I’m going to throw anything that expands my mind in here, like books, conversations, improv, podcasts, etc. Being open to discovery and having a learning mindset is such a great way to live.
- I want to make the world a better place. Making some sort of meaningful contribution is really important to me, whether it’s touching one person, a hundred people, or a million. That can mean so many things, I know — but bringing people closer together through technology and experiences so that we can share, learn, understand, and grow together is what I’ve landed on for my how for now.
- Time is super precious. This is it. You don’t get to go backwards, only forward. Knowing that, I want to spend all of my time thoughtfully, exploring my curiosities and doing things that I care about, rather than being pulled around by notifications, expectations, or fear.
In every place I visited, I found inspiring people whose determination in pursuing their goals and passions pushed me to uncover mine. From Stephen Torres and Mike Gulotta in New Orleans, who are doing badass work in the food scene there, to my buddy Garrett Loh in San Francisco, who’s trying to shorten the drug development cycle, I watched people pick apart their insides, push past the uncomfortable, and propel themselves forward.
As I made my way around the country, I found myself evangelizing being radically candid about whether fear or growth drives our decision-making and opting only for choices that stem from the latter. Somewhere near Gold Hill, Nevada, I finally admitted that I didn’t want to strike out on my own out of fear of failure. Back in Chicago, over breakfast with Chris, I decided that would no longer be the case. Today, I eat the dog food. It’s pretty scary, but I’m in love with it.
Getting back to Larry Summers’ exercise, we spend a lot of time analyzing the products we build, being thoughtful about the companies we grow, and evaluating the career decisions we make. But it shouldn’t stop there. Why is strategic planning limited to our professional worlds? Shouldn’t we also think about what our future lives look like holistically? Knowing what’s important puts you in a place to get to success and fulfillment. Not doing that homework means failing to live up to the original vision. Stalling. Being backed into corners.
When I first got home again, I was antsy. I loved the dynamism of constantly moving and changing things up. But over the past few days, since I’ve found this exercise again, I’ve realized that I’m ready to stay put for a bit and get to work. I know what makes me happy, and I know what my next step is — so now, all that’s left is to take it.
I’m grateful for this trip, and I’m grateful for all of the people who have been a part of it. I’m going to close this out with another line from Geoff Teehan because he just says it so well: “My appetite to do amazing things has never been so ravenous. I’m excited to see what happens next because it will be me, making it happen.”
Today is the beginning of the rest of our lives.
So was yesterday, and so is tomorrow.
- I have no business editing videos, but if you’re curious about what the trip looked like, I stitched together some of the videos I took along the way here.
- I’ve recommended Give & Take to at least one person every day since I’ve been back. If you haven’t read it yet, get it.
- When I got back to New York and finally put down my own roots again, I texted the number on James Altucher’s blog to say thank you. He responded!
- Rock climbing is an oddly excellent analogy for life.
- Inspired by my friend Julia Murphy, I started using 1 Second Everyday to document my trip. I now have two months full of videos. It’s a wonderful exercise in gratefulness.
- New Orleans is awesome. Go. Now.