Halfway Through My Professionally-Acceptable Two-Year Experiment

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10 months ago, I published a blog post on why I decided to go to business school, despite my not-so-traditional career path. Believe it or not, the blogger —> M7 MBA —> ??? is not a well-established career arc.

The tl;dr of my thought process was that business school would 1) give me a two-year window to experiment with and build out my own “thing,” broadly defined as writing and exploring various revenue-generating activities online, 2) force me to commit to living in NYC for at least two years, as I knew in the back of my head that this was the right move and 3) provide me with a social group of interesting and ambitious friends around my age.

And so far, all three of those reasons have proven to be true. But as I’m rolling into my second year of business school, the stakes feel a little bit higher because a lot of things that felt so far away are no longer all-that-far away.

In 2021, I told myself, “Travel for a year, then do business school for two years, then you’ll have it all figured out.”

In 2022, I told myself, “Now you’ve traveled for a year, but you have two more years of business school to figure it all out.”

Well now it’s 2023, and it feels like the time that I have to “figure it all out” is going by more and more quickly. (This feeling likely stems from the fact that several of my friends are now receiving return offers for full-time jobs at the conclusion of their summer internships.) Last week, the weight of “figuring out the rest of my life” hit me, and my mind wouldn’t stop racing.

Don’t get me wrong, I enjoy the niche that I’ve carved out as the “blogging and running a finance newsletter for a meme page” guy, and I’m making more than enough money to support my lifestyle.

But still, I couldn’t help but wonder if what I’ve been doing at 24, 25, and 26 is the same path I want to be on at 28, 29, and 30.

And if it’s not, well… I probably need to figure that out. Soon.

Pre-business school, I thought this whole process would be black and white (Note to self, nothing is ever black and white). The plan was simple: I would keep writing and growing the blog, I would keep editing Exec Sum, and I would charge more for ads as my following grew until I was making some significant but undefined sum of money from said ads.


But as I continued down this path, my plan grew more complicated. A few observations that I have made over the last year or so:

The ad market doesn’t go straight up over time, and I wondered if it was too risky to burn the ships and go “all-in” on the blog.

What if my writing would benefit from me having a more traditional job, on top of the blog? If nothing else, it would give me relevant material to pull from.

Even if I didn’t pursue a more traditional job, would it benefit my personal branding and make me a more credible source if I began writing for a more established media company as well?

People also give you a longer leash to “figure it out” and “do your own thing” when you’re a full-time student. That leash quickly disappears after you walk across the stage.

Building on the last point, a lot of “post-MBA” opportunities disappear once you are in your “post-MBA” life.

There are plenty of valuable ways for me to leverage Columbia, both in promoting my own endeavors and in making me a more appealing candidate for other jobs, but it’s much easier to do that while I’m still a student.

The “idea” of doing your own thing sounds exciting and adventurous, but the reality of not always knowing when and where your next paycheck is coming from can be terrifying.

“Doing my own thing” does, however, give me leverage and far greater upside. Working for someone else, especially if it comes at the expense of building my own brand, following, and email list, could be a short-term decision with long-term ramifications.

All these realizations, and more, have been on the forefront of my mind lately, making it difficult to discern what exactly I should be optimizing for at this point. Thankfully, my blog and my general internet shenanigans have been doing quite well, and I’ve been approached with multiple business and content-related opportunities over the past few months.

But weighing prestige and success and freedom and leverage and money and risk and time commitment and everything else to make the correct decision has proven to be quite difficult in my quest to hit “escape velocity” before graduation in May.

So that’s where I’m at right now. Maybe this process ends with me accepting an offer to write an opinion column or newsletter for a larger media company. Maybe I launch a podcast. Maybe I dabble in a regular job, or maybe I say “screw all of that” and triple down on Young Money. (Though regardless of the path that I choose, Young Money will be a part of it.)

So here I am halfway through my two-year business school experiment, and I have no idea what this next year is going to look like. This blog is my attempt to put my scrambled thoughts into words and navigate where to go next. Thank you for sticking along for the ride so far.

- Jack

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