Know What You Don’t Want To Do

I grew up in relatively high-pressure environments where I was surrounded by peers who seemingly all knew what they wanted to do with their lives. My high school was insanely competitive – 50 boys to a class, and in my class, 9 of the 50 were accepted early decision to Harvard. With the exception of a couple of athletes in that mix, I think the remainder all knew they were vying to get into Harvard as soon as I had met them in 7th grade.

The same was true in college at Princeton. Most of the kids I went to school with had a plan. They knew they wanted to work on Wall Street so they pursued majors in Economics or Financial Engineering. Or they wanted to get into consulting and had already been brown-nosing to get to someone’s parents who might get them a cushy summer internship. Then of course you have the doctors and the lawyers who were already planning ahead for graduate school.

I think there is a bit of a danger in having your heart set on something, especially at an early age. In the same way I encourage people not to have too much conviction in their own ideas (like their political beliefs, for example), the same is true for your wants and desires. You always need to be open to the possibility that you are wrong and that the way you feel about something may not be directly aligned with what is actually best for you. At the end of the day, we are not our feelings, and putting all your eggs in a basket that may disappoint you is all the more frustrating when you have not hedged your bets in any way.

Perhaps my saying this comes from a place of bias. After all, I think I have lacked intentionality throughout much of my life because my de facto character is to be more laissez-faire. My mindset has always been that I am determined enough to “figure it out” as I go. That was certainly the case in both high school and college. And while it is certainly true that getting into Princeton would be deemed an accomplishment by many people, I never had my heart set on it when I was in high school and quite frankly, in retrospect, the rationale for my decision was ultimately a bunch of hogwash and confirmation bias I developed after just having a good vibe about it when I stepped foot on campus.

When I got to college, my initial intention was to work in finance. It’s embarrassing to say this today, but I honestly don’t think I fully understood what that meant at the time. I just knew that a lot of my friends did it and that it was probably lucrative. Midway through my sophomore year, I had an epiphany that I was selling out. I did not enjoy any of the work I was doing in school and I did not feel compelled by the type of career it would lead me to. I did not like all of the social climbing that my friends seemed to be engaged in for the sake of landing seemingly important internships in New York City over the summer. I didn’t like needing to pretend to like people that I didn’t like.

I remember very suddenly dropping my Economics major and declaring English as my major instead. To top it all off, I pursued Certificates in French and in Creative Writing. For the remaining two and a half years at Princeton, I spent a lot of time reading all sorts of literature, watching films from all over the world, and doing a ton of workshopping on short stories with authors like Joyce Carol Oates and Edmund White. My friends made fun of me and joked that there was not really a viable career path for me, but I didn’t really care very much.

My senior year of college, I applied for jobs all over the spectrum. I applied for jobs in sports because I had worked in sports (we’ll get to that later). I applied for teaching jobs, and received several offers. I also applied for consulting jobs and was laughed out of the room when recruiters came down to campus and asked me to perform thought exercises like “How many pennies do you think there would be in a mall?” That spring, I wrote my creative thesis, How Boys Learn, which I later adapted into a published book in January of 2024. The book got rave reviews from my thesis advisor, Edmund White, and the other literary titans that were on the faculty.

I wound up in tech sales. The reason I ended up in tech sales was because the job description said, “The harder you work, the more money you’ll make.” It actually wasn’t the money that spoke to me. It was the control. I liked the idea that I was directly responsible for the outcomes in my job, my career, and my life. I had learned through previous experiences that not being in control often scared me. I have not looked back since, and the communication skills I gained from my education have gone a long way for me, but also in the books I have written and the thought leadership content I have shared for many years.

In taking that tech startup job, I turned down a role with the Pittsburgh Pirates. Growing up, I had been a die-hard baseball fan. I would watch every single Red Sox game and I knew everything about every player. In high school, I got an opportunity to start working on the Grounds Crew. At first, this seemed like an awesome job. And it kind of was for awhile – I got to see the players around and I could go to any game I wanted. But it was also a minimum wage, physical labor type of job that required over an hour commute each way, very early mornings, thankless grunt work (like cleaning dugouts and bathrooms the morning after a game), and occasionally shifts that were as long as sixteen hours.

The summer between my junior and senior year, I landed an internship in the front office. As a kid, I wanted to be an athlete, but as I got older and realized this dream was unrealistic, I transitioned to wanting to be a sports executive. I figured this job in the front office would be a great steppingstone for that as I was working for the late Larry Lucchino who was CEO of the Red Sox at the time. The job was interesting and I got to do some pretty cool things, but I also had a major takeaway from the experience: the prevailing sentiment in sports jobs is that many people would kill for those jobs, so the employers don’t need to go out of their way to make you happy. This means you end up with kind of an average experience in terms of compensation and culture and so on outside of the “coolness” of working in sports. Once the aura of sports had worn off on me, working in sports did not seem so appealing any more.

I’m glad I had that experience because moving to a brand new city like Pittsburgh to work for a team that had been very bad (and continued to be very bad) would have been pretty challenging. Considering how low my pay was going to be and that my job was to sell tickets, there is a very good chance I would have convinced myself this was my dream job only to find myself looking for a brand new job and place to live after 90 days. 

In the early stages of my career, I sold into the higher education space. This actually was a very good thing for me. I built myself into a bit of a thought leader in my space on the topic of location-based social media. Fifteen years or so ago when this was going on, you just had the advent of location-enabled applications on your mobile device. Back then, I was predicting that ride-sharing apps (Uber, Lyft, etc.) and dating apps (Tinder, Hinge, etc.) would become popular, and that social applications (Foursquare, Gowalla, etc.) would go extinct.

I enjoyed being in this space because I felt for awhile that I was contributing, adding value, and building a great network. Eventually, I left that space. It wasn’t until after I left that I realized how bad I had had it. Selling to buyers who did not come from the higher education space was a million times more enjoyable. There are a lot of reasons for that, but the most important one (which really trickles down to all the other reasons) has to do with (what I perceived as) a sort of smug and condescending attitude people have in the higher education administration space. This condescension informs the way they treat people. For example, it was not until I left that industry that I realized that it was, in fact, rude for a buyer to just not show up to a meeting. Decision-makers in marketing roles had no actual background in marketing but were instead just graduates of the university they worked for, some weird type of nepotism where you are rewarded for paying tuition or going to a graduate program to get a degree in Higher Education Administration. All the while, these same decision-makers insisted on buying billboard ads instead of advertising where their prospective students were: the internet. All these types of things were common in that space, even as schools continued raising hefty tuition prices and others shut their doors due to poorly executed business plans. 
When it comes to figuring out what you want in life, I think one of the best things you can do is figure out what you don’t what to do. A lot of times the things you don’t want to do can help inform what you want. If you learn that you cannot be in a pressure-cooker of a professional environment from a specific job, it does not just rule out that job – it rules out many other jobs that have the same type of environment. Through every bad or negative experience you have, you learn something that helps you make the next one better. It doesn’t mean we don’t keep making mistakes – of course we do. But hopefully the questions we ask and the way we form our decisions improves significantly along the way.