Escaping The Meatball | #242

October 7th, 2023: Greetings from Bali. We took a short trip to one of our favorite places since it’s pretty close to Taiwan. I spent six weeks in Canggu, Bali with my friends Jay and Jonny in 2019 and it changed almost everything about how I saw my path and what was possible. I am planning on sharing some reflections on how I approach travel next week so feel free to send any questions!

---

This issue is sponsored by Foster

For those on a Pathless Path, writing well is a superpower. I’ve been shocked at how things I’ve written have spread online and changed the direction of my life—introducing me to new people, opening up new opportunities, and giving me the confidence boost I didn’t know I needed.

I’ve taken and helped facilitate multiple workshops with Foster and I really love their deeper, more human approach. They are launching their next “season,” a one-month facilitated experience designed to help you discover your voice as a writer, get unstuck from patterns of perfectionism and doubt, and hit publish on something you’re deeply proud of.

They’ve titled the experience A More Beautiful Question which makes me think of the writing of Charles Eisenstein, one of my favorites. The deadline to apply for their next cohort is October 13th.

---

June 2008, Boston MA

I had spent the prior year working at GE Aviation, in a finance leadership training program. I was supposed to spend two years doing four rotations in different departments of the company but only lasted two. My first was in Cincinnati, Ohio, and looking back it seems that I got to experience the final days of the organization man reality. I had a 30-minute commute, a mandatory 8 a.m. start time monitored closely by a boss named Carol, a cubicle in a massive room with 30-foot ceilings that only let sunlight in at the top of the walls, and lots of pressure to talk and perform in certain ways to be seen as a good GE person because it was obvious from the people that had been injected with the Jack Welch Kool-Aid in the 90s that I would want to spend the rest of my life working for that single company.

But I felt a sense of doom. I had gone from being excited to work at GE in my first internship there in 2006 to becoming convinced that this company was not heading in the right direction and that I was a terrible fit for a company with hundreds of thousands of people. The successful path for people in my program was to join something called corporate audit staff, where I would continue rotating to different GE businesses around the world for at least 3-5 years. After that, I’d be on the “fast track” to become a CFO of a division sometime in my 30s. I realized that to follow this path was to devote myself to GE above everything else and to move wherever the company wanted me to go. Some people loved this environment and thrived in it but the more I heard from people fifteen years ahead of me, the more I was convinced I didn’t want to devote my twenties to life inside the “meatball” as people half-jokingly called GE.

The meatball

Even at that time, I had a default skepticism toward work taking over too much of my life. While the hours at GE weren’t crazy, I realized that letting a company determine where I lived was a major sacrifice and that I didn’t really want to let a global talent strategy and my ability to be a good GE citizen dictate where I would be spending my twenties. This became quite clear in my second rotation at GE when I moved to Jacksonville, Florida as the only member in that location of my eighteen-person program. While it was pretty cool to be moving to warm weather in the middle of January, the excitement of the move faded quickly when I realized I had no one to hang out with. My manager was four years ahead of my path but had a family and was pretty dedicated to his work. But for him, he was on the right path as LinkedIn tells me he became a CFO about two years ago.

The apartment complex I lived in was called Paradise Island and it was the first and still only time I have ever lived alone in my life.

Paradise Island

But instead of a paradise, it felt a bit more like a dystopia. This was about a year before the housing crisis and if I had been better at putting the pieces together maybe I would have realized such a vast complex of hundreds of apartments should have more people.

Most days I would come home from work, work out at one of the four gyms on the campus, wander around the empty parking lots and trails, and then head home, parking myself at my DESKTOP COMPUTER so that I could talk to my friends still in college on AIM, begging them to come visit me. It’s clear that I was drifting into a low-grade depression and a couple of months into this routine, I was pairing my nightly computer sessions with one or two Busch Lights. I had already felt a bit down about my life after seven months at GE but at least in Cincinnati, I had a good group of post-college friends who were down to party most weekends and we could pretend we were not actually spending the rest of our lives in cubicles. I did make a few earnest attempts to meet people in Jacksonville and even filled out a dating profile on Yahoo! Personals (yes, really) but ultimately gave up after a couple of months and more or less committed to quitting my job and moving to Boston with or without a job at the end of my rotation that July.

And once I made that decision I started dropping the ball on my work at GE. I did the minimum necessary, stopped volunteering for committees, and studied less for the exams that were part of our program. I would go home from work even earlier and sit at the computer, still trying to convince my friends to come visit (some eventually did come!) and spending all my time searching for jobs. At one point I had no idea if I was going to find a job and I decided that I should take advantage of the fact that I had no social life, and signed up for the GRE. I studied intensely for about two weeks, doing practice tests by the pool. I got a solid score, one that I thought was good enough for several engineering schools in Boston and I figured that was a good enough narrative for starting my life over when I was going to walk away from GE.

As I was writing this I was curious if I had any pictures from this period. I have vivid memories of sitting at the going to the gym each day watching the trainer that was training the divorcee while always hitting on her, sitting by the pool reading my GRE book, and having lunch by myself at work because no one I worked with “took lunch.”

But for some reason, there are no pictures. The first picture that pops up from that year is me sitting at Fenway Park, grinning with excitement at my second chance at launching into the real world.

That grin was one of relief because I had indeed landed a job and smoothly executed a mini-reinvention of my life only 12 months after graduating from college. It was actually this experience that helped me realize that we have more freedom in our lives than we can imagine and it might be worth thinking about that and taking action on it every once in a while. It’s always amazed me how much people complain but then do nothing about their complaints. In my twenties, I used to annoyingly propose action steps to other people who were complaining but I’ve since realized some people just like to whine. I’ve always been incredibly impatient with myself when I slip into a whining state and instead of continuing I start dreaming up ways to find an escape hatch or a third door that no one told me about.

In my first week in Boston my all-time favorite sports team, the Boston Celtics, won the NBA championship, something that had not happened in 22 years, and I took it as a sign from the ghost of Red Auerbach that I was meant to stay in Boston and that I was on the right path. I was living with friends, had a job I enjoyed in an office that still remains the best place I’ve ever physically worked, and a city I was excited to explore over the coming years. I really felt as if I was the luckiest person on the earth.

It was also a dramatic change of pace and looking back it’s clear I was getting an early preview of the new economy. At GE, I worked only with people in my physical office, relying on in-person meetings and printed paper reports that we would pass around and fill in with pen. Our entire campus in Ohio was about 70% empty, with the campus’ glory days in the 70s and 80s long behind it and most of the manufacturing having been outsourced to suppliers around the world.

At McKinsey, I worked in a global team with colleagues in India, Europe, Costa Rica, and many places throughout the US. We were told to work from home if we needed to and were given state-of-the-art equipment to make that happen. Our team was even early to embrace video calls, having a morning huddle every morning at 9:30 to connect and share our latest client challenges.

A couple months into working at McKinsey I went to New York City for a week for training. This was where I met Josh, who would introduce me to many people in Boston where he also lived. He had gone to Stanford but seemed to be a master at playing the games that people need to play to land a job at places like McKinsey. I thought I was good at such games but when he told me that he had been working on trying to break into strategy consulting since his freshman year of college and had known about the industry in high school, I realized I had entered a new world.

But this is not why I’m telling you about Josh. I’m telling you about Josh because he introduced me to Ravi, one of the most interesting people I encountered in 2008. I shouted out his reflection meetup last week and was planning on finishing this personal reflection last week but ran out of time. He called himself an entrepreneur and at the time, he was legitimately the first person doing such a thing that I had met in my life. He had a small company called athleague and he was running it out of his apartment with a few other people. They had this loft in the Downtown Crossing neighborhood, a place that people didn’t want to live at the time but is now prime luxury real estate, and had all these working areas set up in the place, including multiple whiteboards. I did a quick search online and found a post from this period. Here is Ravi in 2009:

I was so intrigued by what he was up to but he and his friends were all UPenn, or Stanford, or MIT graduates. They seemed to know more about the world than I did and of the coming tech revolution that would sweep through cities like Boston. But I never even thought once that I could do things like them. I thought I cared about different things.

It’s clear that I was attracted to the obvious freedom that Ravi and his friends had. They could work on what excited them and spend their time how they wanted. But because I had just made a dramatic pivot in my life, I don’t think my brain had any space to consider going deeper. If I could give myself advice at that time, it might be to follow the people that I wanted to be like, not what I desired.

I recently caught up with Ravi and it made me think, what if?

What if I hadn’t landed that job at McKinsey and had to bet on myself earlier?

What if I had followed my curiosity about entrepreneurship earlier?

What if I had been exposed to unconventional paths earlier in life?

In almost every chapter of our lives, we can decide to keep going or shake things up. I’ve often decided that I should shake things up and have always been happy that it seems to lead to much more learning, adventure, and aliveness.

But even if you are actively shaking things up, it’s impossible to avoid the conclusion that there are infinite paths that you didn’t take and that your current path is one of many possible realities you could have reasonably ended up in. This is why this image from Tim Urban is so powerful:

The implications of this are profound and many people choose to ignore it for if we always knew how many different possibilities were in front of us, we would struggle to make any decisions at all. But change is information and I think at the margins more people should look to experiment in their lives. The elders I look up to that seem to have gotten the balance right between exploration and commitment in their lives and as they age they are able to loosen their grip on life and soften into who they are meant to be. I find such people really inspiring and it’s something I hope to get right as I get older too.

---

Thanks For Reading!

I am focused on building a life around exploring ideas, connecting and helping people, and writing. I’ve also recently launched a community called Find The Others. There are weekly writing sessions, monthly “find the others” (literally) virtual meetups, and general supportive vibes.

• You can join Find The Others if you want to hang with us too, or if you are already a subscriber, get access here.

If you’d like to support my journey, the best ways are to:

• Buy or listen to my book, The Pathless Path (or message me if you want to bulk order at a lower price)

• Want to reach 15k+ curious humans? I’m looking for sponsors for 2023 for this newsletter or podcast. Please reach out or book a package here directly.

• Subscribe to my podcast and leave a review.

• 🤳Want To Get Started on Youtube? Friend of the newsletter Ali Abdaal (and his amazing team) have just launched their self-paced course and accelerator program on creating a thriving YouTube channel.

In addition, I recommend all of the following services (affiliate links): Collective for setting up an S-Corp in the US (recommended >$60k revenue), Riverside.fm for HD podcasting, Descript for text-based video editing, Transistor for podcast hosting, Podia or Teachable for courses, Skystra for WordPress Hosting, and Circle for running a community.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.