Lessons Learned from Poverty and Wall Street

“There are no real rules, so make rules that work for you.” –Seth Godin

Six months after graduating from Princeton, I found myself sitting in the office of one of New York’s elite private equity headhunting firms. It was the seventh firm I had interviewed with that month. Waiting for the interviewer to enter the room, I silently practiced my dry, rehearsed pitch. My thoughts drifted. How did I end up here? Why am I doing this?

In answering those two simple questions, I uncovered a simple, but profoundly important distinction: there is a critical difference between defaulting into a smooth narrative of success and choosing to create and live a narrative that works for you. And starting with why helps us consciously choose the more fulfilling path.

To understand how I uncovered this idea and the important implications for your life, let’s start from the beginning.

Show Me the Money

I grew up in Orlando, Florida in a single parent home. On the whole, my childhood was riddled with challenges. From navigating the world without my biological father to changing elementary schools three times, things were rarely easy. Every morning, I checked the cereal box hoping that I wouldn’t find sugar ants or cockroaches in my breakfast.

While I found these circumstances unpleasant, what bothered me most about my youth was the constant economic struggle. In short, I hated living in poverty. Of course, having little money taught me to be resourceful, persistent, and grateful. However, the financial scarcity was something I always wanted to change. From a very early age, I cultivated a relentless focus on improving my economic circumstances to eliminate this source of pain in my life.

The first logical step towards improving my circumstances was getting to a top university. To that end, I put all of my time and energy into excelling in academics and athletics. After a lot of hard work, support from a wonderful mentor, and raw luck, I was admitted to Princeton on full financial aid, which amounted to $250,000. For me, this was just the beginning. I knew there was still a long road ahead to financial security.

Chasing Wall Street

My relationship with Wall Street began shortly after I arrived at Princeton. A week before heading to campus, my now-deceased friend and mentor, Howard Sherman, bought me my first suit and taught me how to use chopsticks at a local Japanese restaurant. These are two of the most valuable things anyone has ever done for me. In my first two weeks, I went to a sushi restaurant with classmates and attended a JP Morgan networking session. My baggy, pinstriped suit at least allowed me access to the elite bankers.

That JP Morgan event was my first real exposure to the world of finance. I had no idea what investment banking was before the event. What stood out at the time was how everyone at the event seemed so successful. Crispy suits. Animal print ties. Polished sentences. Sign me up. I scurried back to my dorm both anxious and exhilarated. Do I belong here? They make HOW much? Are these the “doors” that graduating from Princeton opens?

Shortly after the event, I haphazardly decided I should begin my career in investment banking. Wall Street sounded cool and prestigious. Most importantly, it was the quickest and most predictable path to financial security. This decision strongly influenced my entire university experience, from selecting courses to deciding my concentration.

After hundreds of resume reviews, months of technical preparation, and dozens of networking calls, I landed an investment banking internship with Barclays in New York City after my third year.

It was perfect timing. I took out a small loan to pay for my summer housing and to purchase a few cheap ties. My checking account balance dipped below $250. I lived on street vendor food and held off on doing dry cleaning until I got my first paycheck.

The 10-week internship was my first real exposure to the world of living with more than you need. I was making good money, learning about a new industry, and wearing a suit every day. I received an offer to return full time after graduating. The $10,000 signing bonus would enable me to stop checking my bank account every week. That was a level of comfort I had never had before.

How could I turn that down? I accepted the offer.

The Allure of Private Equity

Approaching my start date, I geared up for a challenging start to my career. The investment banking industry is known to grind new analysts. Fifteen hour days and weekend work are expected. The promise of this intense culture is the ability to work on billion-dollar deals, a tangible set of skills that provides attractive “exit opportunities,” and large performance bonuses.

My first day on the job was an uninspiring set of welcome speeches. What I found most interesting about that first day was the palpable and universal desire to “escape” investment banking. It seemed that the entire incoming pool of 200 analysts was more interested in transitioning as quickly as possible to roles outside of banking than in starting a meaningful career at the firm.

In fact, I did not meet one person who was legitimately excited about building a long-term career in investment banking. The majority of individuals were hoping to land a gig in private equity, an adjacent industry that promised fewer hours, more impact, and bigger paychecks.  

Within four months of starting the job, the private equity recruiting process became a central focus. Private equity firms hire headhunters to find top candidates for their associate hires. These headhunters contact analysts in well-regarded investment banking teams across Wall Street. They ask for polished resumes and introductory meetings before analysts have even closed their first deal.

Before I even understood how to build a proper financial model, the private equity buzz was everywhere. My peers were sneaking away in the middle of the day for calls and interviews with the headhunters. Elevator talk centered around private equity recruiting unless a more senior banker was around. I began to think, I should do this too, right?

With all the buzz, I decided to participate in the private equity recruiting process. For the next 3 months, I honed my resume, covertly scheduled meetings with headhunters, and spent weekends learning about financial leverage and debt modeling. And that’s how I found myself waiting in a headhunter’s office in late December.

A few days after that meeting, I woke up early on a Sunday morning to review my 500-page pile of interview prep material. After a few minutes, I asked myself the essential question that completely changed my understanding of the right path forward: Why am I doing this?

Start with Why and Create Your Own Narrative

“I’d tell men and women in their midtwenties not to settle for a job or a profession or even a career. Seek a calling. Even if you don’t know what that means, seek it.” – Phil Knight

Investigating the why of my decision to recruit for private equity was an enlightening exercise.

On the surface, a career in private equity offered a compelling and smooth narrative: a challenging and prestigious profession, smart colleagues, unparalleled compensation (upwards of $300,000), and connections to top-tier business schools.

Growing up, this is exactly the narrative I was taught to praise. And as someone who spent their life trying to escape poverty, the level of financial security and stability was incredibly attractive. Private equity aligned very well with my uninformed vision of what my personal narrative should look like.

But there is a problem with this line of thinking: in pursuit of the smooth narrative of success that private equity offered, I failed to dig deeper into why I was pursuing this path and how I even felt about it.

Instead of asking myself the difficult question of what I want to spend my limited time on in this short and unpredictable life, I defaulted to the comfortable narrative. I chose comfort over courage. I failed to ask myself why I was doing what I was doing.

And in doing so, I risked going on a potentially dangerous path. The dangerous path is the one that checks all the boxes, but feels miserable and unfulfilling 6 months in. It’s the path that champions how other people will perceive you instead of how you genuinely feel about what you are doing. It’s the path that leaves you wondering what you could have accomplished had you taken a leap of faith.

Once it was clear that I was pursuing a narrative of success, rather than something that drove me on a more fundamental level and got me excited in the morning, I immediately chose to opt out of the process.

Of course, making this decision was scary and felt risky. At the time, there was no clear alternative path and certainly not one that offered the same level of financial security. But in asking myself why and making the decision to pursue the unknown, I felt a huge relief. For the first time, I started listening to how I felt. I was no longer chasing the money. With a small layer of financial security, I was now thinking more consciously about what I wanted out of a career. This was empowering.

And things have worked out pretty tremendously since then. I ultimately decided to drop the cubicle and suits and work remotely for a startup. With the increased flexibility, I have spent the last year and a half traveling to over 25 countries in South and Central America, Europe, and Asia.

In the process, I’ve uncovered a whole set of additional passions that I had no idea existed. One of those includes my commitment to living a conscious and intentional life and helping others to do the same.

In the end, there’s no one correct path for anyone, including me. However, in asking yourself why you do the things you do and being very conscious about the decisions you make, you will get closer to a way of living that genuinely excites you on a daily basis.

Life is not about a smooth narrative where you tell the world 20 years from now that your life was a success because you accomplished a, b, and c. That’s not how we create and feel meaning. We find meaning in the person we become throughout the uncertain journey we all live. To that end, it’s important to stop worrying about what you want to tell the world and start listening to what you actually want to do and who you want to become.

Live a more conscious and intentional life while you still have the opportunity to do so. Start by developing a deep understanding of why you do the things that you do. And relax a little. If you can understand your why and accept that there are no real rules or things you have to live up to, you can start creating the world that you want to live in.