The moment money stopped feeling like freedom

Sun. Warmth. Vacations. Swimsuits. Fireworks.

Many consider Summer to be the best season of the year. Investment bankers especially. If you walked into any Goldman Sachs’ office, the analyst bullpen would probably tell you they’ve been counting down the days. Though, junior investment bankers don’t just prefer Summer for the backyard BBQs. In banking, it’s called bonus season. Most banks on Wall Street pay their analyst and associate investment bankers their annual bonuses sometime in the June to August window. The bonus is paid in cash as a lump sum usually equating to 50-100% or more of their total annual salary, often pushing total compensation for mere 22-year-olds to over $200,000. For example, a first-year analyst’s salary could be $115,000, add their annual bonus of $100,000, and you get their total compensation package of $215,000. You can see why this would indeed be an exhilarating time for a kid straight out of college, barely knowing how to type an email.

Nonetheless, the monetary incentive is usually what makes this lane of business so enticing to the young bucks, myself included when I entered the IB task force. Grinding through finance modeling workshops, banking info sessions, honors classes, technical interviews, superdays, all on top of getting an absurdly high GPA just to get your resume past every bank’s grim reaper (the paper shredder). Though, looking back, getting the job turned out to be the easy part. There were plenty of banks hiring from all over the country for entry-level banking positions. The true “Survivor reward challenge” was what everyone had warned me about: 2-years of investment banking analyst hell. A “pledgeship” of sorts to enter the world of finance. The esteemed bankers that came before you tell you to do your time, and you’ll be thankful when 2 years from now you’re in you’re in the promised land: a cushy private equity seat, making more money while working way less. The optionality from there will be endless, you’ll be able to pick any high-paying, finance job you want.

Enter me, a 23-year-old kid, a fresh IB analyst on the street who just wants to make as much money in as little time as possible, no matter the cost. I was tired of having an all but dried up bank account for the full extent of my collegiate career. So it began, I put my head down and got to work. I wore a suit and tie daily. I did what I was told, often times the “grunt” work. I stayed up late, often until 2:00 or 3:00am. I printed all of our pitch decks and double counted each page. I made mistakes. I built entire financial models for new clients. I once had a director tell me, “Do not move from your desk.” Mind you, this was 11:00pm the day before my grandfather’s funeral. I missed dinners and evenings with friends. I spent every Sunday in front of the blue screen fixing my bosses “comments”. And I regretted every morning I had to go up to the 64th floor again. I did what it took to survive. So, when July came around the following Summer, you bet I was looking forward to the big payday. Finally, the day that would equalize all of the hardship I just went through for the last 12 months. The director in our office, my boss, calls me into his corner office and I finally realize this is the big moment. As I’m walking over, I’m pondering how I’m going to hold back a big smile and remain professional, like I’ve done this before. Yet, I don’t feel like a smile is about to crack. I step through the door. Sitting down on the other side of his solid oak desk, I wait for him to take his eyes off the computer. He rambles on for a few minutes about how we’ve done some good work this year, and how I’m making a ton of money. He tells me my bonus is $65,000. A lot of money, no doubt, though I felt…nothing. I politely said, “sounds good”, shook his hand and headed back to my desk with a completely blank expression on my face. I sat there, still and emotionless. I was now the richest I had ever been in my entire life, and it meant genuinely nothing to me. I was promised a lie. All this money brought me was pain and handcuffs. I was tied down to a job I hated and a life path that wasn’t me.

My identity began to crumble. Having worked my entire educational career to get to a “good” job; then work a gruesome 12 months in the banking trenches, only to find out that money alone wasn’t the answer. The one thing I was after from the beginning. The realization nearly broke me. I quit my job 5 months later, and left for Hawaii, the most remote place I could think of that was still relatively reachable. I spent a few weeks beach bumming, hiking, and surfing, but most importantly getting my head straight. A mid-20s life crisis I called it. Asking myself questions like, “What does my ideal Tuesday look like?” and “What does wealth really mean to me?” I began to imagine all the different scenarios. If I go back and get a finance job, where will I be in 5 years? If I go try to find a less intense corporate job, but still earn a reasonable salary, will I end up enjoying it? In every scenario, one intrusive thought kept returning: money wasn’t the freedom I was actually chasing.

Eventually, something clicked in my mind. Real wealth was optionality. And I’m not just talking about a bunch of high-paying PE job offers. Money of course helps, but it isn’t the root of freedom. Money expands optionality, but it doesn’t create it. For example, you can have money and still be trapped by a job you hate, a city you don’t want to be in, a lifestyle that owns you, obligations you can’t escape, the list goes on. On the flip side, you could have very little in the bank, but have a flexible life design, low recurring expenses, portable skills, or multiple small income streams. If your obligations trap you, then throwing more money at them won’t fix the problem. In the case of a traditional career path, as the career ladder is climbed, more money is earned. However, most often, as more money is earned, the higher expenses rise, thus the tighter the “golden handcuffs”. So, not only will money not fix the problem, but it may make things worse.

Did I make the right decision to leave my high-paying corporate office job? Financially, no. But I wouldn’t trade the realizations I made in my early to mid-20s for anything. My life is no longer a pursuit of money. It’s the pursuit of structure, choices and skills that enable my freedom, my optionality. It’s what I wish someone had told me back in my early days. It’s what I’d tell any 22-year-old before they venture out into the world. Reverse engineer your ideal Tuesday. Know that if you build a life with low overhead, even a modest income can give you tremendous freedom. True wealth is having choices. Money just widens them.

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