"So Why Are You in Business School?"

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"So why are you in business school?"

It is a question that I have received quite a few times over the last couple of months.

I was shocked, and I mean shocked, to discover that I was pretty much the only person in my MBA program who planned to write a blog for a living instead of pursuing something a bit more normal.

But on a serious note, it’s a valid question.

Broadly speaking, business school serves two purposes:

• It helps you advance in your career

• It helps you pivot careers

Because consulting firms, banks, venture capital firms, and startups all recruit from top MBA programs, business school provides a fantastic opportunity to land a competitive job. It is also one of the last high-probability ways to successfully make a major career pivot early in one’s professional life.

The thing is, business school probably won’t directly advance my career (though to be fair, I have convinced 50 of my classmates to sign up for Young Money), and I’m definitely not trying to pivot careers (this blog was the pivot).

So yeah, when folks around campus ask, “What are you planning to do after business school,” and I respond with, “Probably keep writing this blog,” it raises some eyebrows.

And then on top of that, I have a whole cohort of Twitter friends and other creators who don’t get why I enrolled in the first place.

So why am I in business school?

Because it was the next logical step.

I’m going to preface this part by saying that given my current career circumstances in October 2022, if I wasn’t already enrolled in business school, I probably would not apply to business school right now.

I write a blog and edit a newsletter, and I don’t really want to jump into anything else right now. Not exactly a textbook MBA candidate, right?

But I didn’t apply to business school in October 2022. Or October 2021. Or October 2020.

I applied in April 2019, during my senior year of college.

Columbia, Harvard, Stanford, and several other top programs had begun offering “deferred enrollment” options to prospective MBA students. In the typical MBA timeline, you work a few years, and then you apply to a program if the fit makes sense. Columbia’s deferred enrollment program allowed me to secure my seat when I was a senior in college on the condition that I work a few years before starting.

When you’re 22 and you get an acceptance letter to one of the country’s top business schools, it’s an awesome feeling.

At the time, my plan was simple: kick back and work in finance for 2-3 years, go to Columbia, hit the consulting/investment banking recruiting cycle hard, secure an internship, receive the full-time offer, then make bank after graduation.

There are few guaranteed ways to make $200k+ in your late 20s. An MBA from a top business school is one of them. The median starting salary + signing bonus out of Columbia was $180,000 last year.

When you are making $60,000 working as a financial analyst, and you have a call option to 3x your salary in a few years, why would you consider anything else?

The system works. An acceptance letter to a top MBA program is a golden ticket to winning “the game”.

As a 22-year-old just starting his career, I would have been crazy to even consider doing something different.

But craziness begets craziness, and the last few years have been anything but normal.

If Covid never happens and I spend the first two years of my professional career wearing dress shirts to the office instead of a red-and-black checkered nightrobe in my apartment, there’s a 0% chance that I deviate on my path.

But Covid did happen, and my priorities shifted.

So in August 2021, I threw caution to the wind and decided that I would spend one year traveling around and having as much fun as humanly possible before moving to New York. Because, you know, I was going to business school to land a high-paying job to make a bunch of money.

So I spent the majority of last year doing my best impression of Rolf Potts’s Vagabonding. And I wanted to make some money while I was traveling, so I applied for some writing gigs. No one hired me, so I started my own blog to build a portfolio of work. And then whole writing thing took off. A lot of people read my stuff now, and I can make money from it as a result. How cool is that?

But in December 2021, not that many people were reading my stuff, and I had to let Columbia know if I was planning to start school the next August.

The whole reason I had started traveling a few months earlier was to squeeze every ounce of fun out of a 365-day window before “getting my life together” in New York. That was it. The writing thing? I just wanted a remote writing gig that could generate some cash until school started. This was never supposed to be a career.

This was never part of the plan.

So when you have a blog that has like 1,050 readers and you haven’t made a cent from it, of course you tell  them that you plan to start school in August.

That was the plan, after all. It was the only plan I had.

And then the spring and summer roll around.

The blog is closing in on 10,000 readers. I haven’t “made it” per say, but I know how to “make it.” I have momentum, and momentum is the most difficult force in the world to stop.

So around May/June, I faced a crossroads. I had spent nearly a year abroad, on and off. I had visited friends all over the US, and I could still pull out of school and live anywhere I wanted. I could backpack Asia for a year. I could spend four months in Australia. A decade in Europe wouldn’t be enough time to experience everything I wanted to experience there.

I could move to an entirely new city and start from scratch. Around this time, I actually pitched two of my buddies on the idea of potentially moving to Austin, TX.

But in the back of my head, there was always this thought: I needed to stick to the plan.

The plan was New York City.

The plan was Columbia.

That was always the plan.

But what if I don’t want to stick to the plan? What if I want to go all-in on this vagabonding lifestyle I’d grown accustomed to? What if I want to do something entirely different?

It was a big struggle of mine, because I felt that moving to New York for grad school would limit my ability to travel. It would slow me down and hinder my freedom.

But New York just made the most sense. I had built a huge network of writers, creators, investors, and operators over the last year, and pretty much all of them either lived in New York or visited frequently. I know remote work has been beneficial for many (myself included), but in-person connections are exponentially stronger than those that only exist online. Moving to NYC and turning my Twitter friends into real-life friends would be a 10x move for my career as a writer.

And what about Columbia?

Even in May when I had built some momentum, there were risks to my plan. What happens if the economy really takes a nosedive and ad revenue dries up? What if I burnout and no longer want to do this every week? What if I need a pivot?

Business school would be a two-year window for me to experiment and test things out while still having the option to secure a good, more traditional job at graduation if needed.

And it’s not like business school would hurt my writing career. If anything, an MBA from Columbia would increase my pedigree as a finance writer, especially in the eyes of those who aren’t as internet-savvy.

I would have an opportunity to take a variety of classes taught by some of the sharpest professors in the world.

But the biggest benefit of Columbia to me was the social aspect. Being from Georgia, I didn’t have many close friends in New York. Making adult friends is hard because everyone is so invested in their own lives that it’s difficult to form those same bonds that we do while we’re in college.

The best way to quickly make friends in a new city?

Go back to college.

Business school is interesting because the social dynamics are similar to college in that you have a super diverse group of people from all over the place now living, working, studying, and hanging out together in a tight community for two years.

But instead of the collection of people being 18-22 year olds trying to figure out where they stand in the world, it’s ambitious ~25-30 year-olds who have a stronger understanding of who they are and what they want to do.

And of course, they still like to throw down and have a good time as well. Rugby team happy hours on Wednesday are undefeated.

So moving to New York would level up my game as a writer, while business school would hedge my bets, improve my “brand”, give me a chance to learn from some really smart professors, and provide me with a built-in friend group of some really interesting people.

The tradeoff at this point was binary:

Did I value all of this stuff over pure, unadulterated freedom?

Business school is a two-year commitment that would someone limit me geographically. Can’t spend February and March in Buenos Aires when you have a valuations exam in Manhattan!

And this idea of a two-year commitment scared me until I read this piece by David Perell: Hugging the X-Axis.

That article resonated with me.

When I started traveling, I had a simple goal: I wanted to do as much fun, new, different stuff as possible before moving to New York. My life during this period looked chaotic, but it was quite intentional. Every night spent in a hostel in Prague, every last-minute train across England and Scotland, every adventure in Argentina was a part of this goal.

But there was no intentionality behind this freedom that I was debating now.

I wanted freedom for freedom’s sake. I was worried that I would lose the ability to go and do anything anywhere whenever I wanted. But this new desire for freedom wasn’t driven by commitment to a goal, it was driven by a fear of commitment entirely.

And that’s when I realized I had freedom entirely wrong.

Freedom isn’t valuable because it liberates you from the burden of commitments. Freedom is valuable because it allows you to choose what to commit to.

The key, of course, is that you do eventually have to commit to something.

Having an abundance of freedom but a scarcity of commitment is like making millions of dollars and failing to spend any of it: a waste of a valuable resource.

And at some point I needed to commit to something. I needed to go all-in. Would vagabonding for another 12 months, hopping from city-to-city on an undetermined path, really be the best way to spend the next year?

Part of what made last year’s travels so important is that I knew they had an expiration date. When you start with the end in mind, you are far more intentional about the present.

(That’s good life advice, by the way. Working backwards from the “you’re gonna die” part is an effective method for figuring out what direction you should take in your own life. Shoutout to Dr. Jim Jackson for the advice.)

Remove that expiration date, and suddenly exploring becomes wandering, and the vagabond becomes a drifter.

And there was an expensive opportunity cost associated with not making the New York move. The people not met in-person, the conversations not had, the relationships not nurtured.

That matters.

I needed to commit to moving to New York, but my one “fear”, if you can call it that, was my lack of social group in the city.

Business school would force me to commit for at least two years while giving me the social group that I desired. So after weighing the idea in my head for a few weeks, I decided to commit.

And you know what? Despite the gauntlet of mid-terms that I’ve had this week, this was the right decision.

I’ve already met more interesting individuals from the online content space in my two months in NYC than I had in total before this. My classmates at Columbia are awesome. We have startup founders and military veterans. People who worked for Goldman and people who worked for the government. Some of my best friends are from New York, Philly, Colombia, and India. And everyone is just a ton of fun. It’s like all the good stuff from college, minus the cringe aspects of being 18 years old.

And of course, I’m learning a lot too!

So why am I in business school? Because without it, I wouldn’t have been able to “commit” to my craft for the next two years. I wouldn’t have moved to New York, and I would have missed out on everything and everyone that the city has to offer.

So yeah, traveling is fun. Living out of a backpack is fun. Doing dumb stuff in other countries is fun.

But you know what? Being a business school student in New York City is pretty fun too.

- Jack

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Jack's Picks

• Derek Sivers was a guest on the Danny Miranda podcast a couple of weeks ago, and the episode is jam-packed with gems of wisdom. Check it out here.

• Business Insider published a funny, but fascinating piece on the biggest charlatans in financial markets over the last couple of years.