Adios, Business School.

There went two years. What's next?

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After a brief two-week hiatus, we are back. The last couple of months have been hectic as I was juggling business school and a new job, but I graduated from Columbia on Saturday, and now I’m wrapping up my first week in the office with no class interruptions.

Now that I am, for the first time in like 5 years, on a somewhat regular schedule, I’m going to resume publishing a new blog post every Thursday, as well as my monthly recaps and content roundups. For today’s piece, I wanted to reflect a bit on my last year in business school.

Let’s get started.

A pattern that is common in our lives:

  1. One stage of life is really, really good.

  2. Committing to that next thing, whatever it may be, marks the end of your current stage.

  3. You don’t want to close the door on your current stage, so you rationalize your indecision.

I experienced this pattern in my business school journey a few times. Two examples:

1) I remember wondering in May 2022 whether or not I even needed to go to business school. For context, I had, on a whim, quit my job and decided to backpack around the world for a year in August 2021. After eight months, I’d figured out how to make a living writing online, and as a 25-year-old with a rusty grasp of the Spanish language and a lot of SkyMiles, life was good. People enjoyed my writing, I was quickly building a sizable following, and I could do my job, which consisted of writing blogs and editing a newsletter, from anywhere in world, so why would I confine myself to New York for two years?

I told myself that my hesitation stemmed from me questioning the economic value of an MBA as my writing was taking off, but quietly, I knew the economic value was obvious. I was writing about finance. An MBA from Columbia would, if nothing else, increase my credibility as a writer. Beyond that, I knew NYC was the center of media and finance. Everyone who is anyone either lives here or visits frequently, and I would be crazy not to maximize my exposure to as many valuable connections as possible.

My hesitations about business school had little to do with Columbia’s value prop and more to do with my reservations about moving on from the vagabonding stage of my life. The digital nomad thing was pure, unadulterated fun. I could move from hostel to hostel every few days, in Spain today and Sweden tomorrow. If I wanted to visit friends in Austin, DC, Los Angeles, or London, I could rent an Airbnb for a week. When I wanted to improve my Spanish, I spent two months in Buenos Aires. I had tentative plans to visit Australia. Thailand. South Africa.

School would, for at least two years, ground me in New York, limiting my ability to live abroad, and part of me wanted to keep the party rolling. But I knew, in the back of my head, that moving to NYC and starting school in August 2022 was the right move.

A big reason that I enjoyed my year of travel so much was that it felt like an adventure. But adventures are only adventures as long as they have expiration dates. If you remove that constraint, an “adventure” simply becomes your life. In my case, forgoing business school would have meant I was no longer a thrill-seeking vagabond. I would have been a drifter.

I didn’t want to be a drifter.

So I paid my deposit and moved to New York.

2) I remember wondering, in school, whether I needed a real job. I didn’t recruit for a summer internship in Year 1. I had my blog and Exec Sum, the newsletter where I served as editor. I valued my independence, and that independence served me well in school. I went on trips and visited friends as I wished, I didn’t have to stress about networking events and coffee chats, and I was still generating income as a student. More importantly, I understood the long-term financial upside behind what I was doing.

However, as Year 2 began, I faced a crossroads. Was I going to parlay business school into a full-time job, or would I keep rolling as an independent writer and creator? The upside of independence was obvious: flexibility and control. However, independence also came with a cost: business school is a convenient time to explore other career opportunities (that is, you know, the point of going to business school). If I doubled down on the independent creative path, it would have been much, much harder to go back later. I told myself that I needed to be cautious about giving up my independence, but really, I was quietly more worried about locking myself in to the next stage, whatever that happened to be. Writing my blog and working somewhere else weren’t even mutually exclusive activities. It was just a different version of the school vs. travel debate: the right answer was obvious, I just told myself it wasn’t.

Ultimately, I realized that my most valuable outcome would stem from leveraging my experiences as a writer and editor with my time at CBS to land an otherwise hard-to-reach job. After exploring a few different opportunities, I accepted an offer to join Robinhood’s media venture, Sherwood.

Life is nothing more than a series of stages, one after another. Our problem is that we often enjoy a particular stage so much that we’re hesitant to move to the next one. Each chapter should be enjoyable, yes, but each chapter should also prepare you for a new chapter that you could only reach by experiencing your current one. And you do, at some point, have to make that leap to the next stage. Ideally, you should make that leap before you feel ready to move on to the next stage, because if you wait until you are ready to move on, you’re late.

Imagine, for example, that I had decided to postpone business school and keep traveling for another year. Then, 7 months later, December 2022 rolls around. I’m tired of traveling for weeks on end. I want to move to New York and start school. But at this point, I would have had to wait until August 2023.

What if I hadn’t taken a job, kept rolling as an independent worker, then realized, in September 2024, that I needed something more stable? The “entrepreneurial business school student” would have had much better luck recruiting than the unemployed graduate. If you know you’re ready, it probably means you’re on a decline. You’re late. Momentum is a real thing, and you need to strike when the iron is hot.

Don’t get me wrong, a little nostalgia for the past and sadness that the current thing is ending is a good thing. It means you did it right. You had good experiences, you formed strong relationships, and you don’t want to let that go. But enjoying an experience doesn’t mean that you should stay there forever. The finiteness of everything is a feature, not a bug. It’s what makes it valuable.

- Jack

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Jack's Picks

  • Ryan Holiday wrote an excellent blog post about the value of building your own platform, choosing “alive” moments, and not worrying about taking credit for everything.

  • I enjoyed this Oliver Burkeman piece about why AI will struggle to replace creative work.

  • Beehiiv CEO Tyler Denk’s newsletter breaking down his journey as a startup founder has been excellent. Big fan of this recent piece on some of his founder struggles.

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