As entrepreneurs or business owners, we’re all guilty of it. The 60–80+ hour workweeks must have made me delusional, because working at my former company in financial services never felt real or truly fullfiling. It was a dream I couldn’t believe, or a spinning wheel I thought I couldn’t leave. Sometimes both. That’s the financial services industry and startup world, right?
Do something you love, never work a day in your life — that’s how the saying goes, right? And I loved my work. Truly, I did. But never working a day? The highs were high, the lows were low, it was nothing but work. I didn’t know something could be so tumultuous. Salesman & saleswoman in finance are great at what they do. I mean shit, I was sold so fucking hard it wasn’t even funny at 22 years old and fresh out of college.
It was good. It was bad. It was toxic. It was exhilarating. And because I held on, it was also never ending. Friends and family told me repeatedly: let go of it. They didn’t understand; how could they? Or were they empathizing with me? When you’ve invested so much of yourself into something, it’s easy — natural even — to develop a sort of tenacity and will yourself to stick it out. After all, you’ve come so far why quit.
Was it healthy? Probably not. At least I had health, nutrition and wellness as a top priority and value in my life. But goodness, isn’t it nice to believe?
“Sleep is for those people who are broke. I don’t sleep. I have an opportunity to make a dream become a reality.” — Eric Thomas
I lived for financial services. I lived for the stress. If you weren’t stressed, you weren’t challenged. And if you weren’t challenged, you weren’t going anywhere. That’s the kind of mantra I fed myself and was fed by others for a couple of years.
The first time I had meetings and work on a Saturday, I complained about it halfheartedly to my friends and family. I joked and said it was a business seminar I was going to. Internally, I was thrilled at being important enough to be called to work and the seminar.
Wow. They need me. They depend on me! Or was I simply jaded? How naive. For an ambitious person like me, it was weirdly addictive. The high was overworking.
I pushed myself to always be better than everyone around me. I took pride in how early I thought I woke up, in how many different things I could successfully juggle, in my workouts, in how busy I was being busy. Hustle, hustle, hustle. I initially felt I was made for the rat race. Then again, I was also foolish enough to believe I could beat it and win — aren’t we all at some point? To work 40–45 years of our lives and end up dead someday is bullshit. Something had to change. And guess what, it was me.
Lost in the ‘What If’
There were a lot of things I genuinely loved about financial services. Many individuals are financially illiterate so educating friends, family and colleagues was rewarding at first. And for a while, it sufficed to keep me tolerant of all the things which truly bothered me about the industry. It was the fear of missing out, of losing out on something great, of screwing up a good thing, that slowly dissolved any intent I had to change the situation.
It always got better too. Every time I considered moving on to something new, my role grew. Amidst high turnover (churning & burning), I outlasted some of my competition. Responsibilities on top of more responsibilities. Independence and studying on top of calling hours, training and more meetings. I caved each time, and I stayed. It was easier. Or at least I thought it was…
That didn’t stop me from daydreaming, though — fantasizing, if we’re being completely honest — about quitting and disappearing into the sunset of Hawaii. In hindsight, I should have recognized that as a bad sign. One that should have never been justified. But hey, they say good judgement comes from experience, and a lot of that must come from bad judgement.
I was caught in a place where I didn’t feel good enough to thrive in my role, but crippled by the thought that I was not qualified enough to find anything remotely close to what I was doing — which I considered an ongoing, growing opportunity too golden to let go of. And whether it was self-doubt that echoed the sentiment, negative self-talk or the atmosphere that reinforced it, there was always a voice in the back of my mind reminding me:
Unhappy? Check your privilege. What if — No. Don’t forget, you’re lucky to be in this position. But what if — No, you should be more grateful… You’re not even qualified — you didn’t even deserve this.
I became a shell of who I once was, feeding more and more of myself to my job, in many desperate attempts to prove my worthiness. I couldn’t remember why I was trying so hard, or who I was doing it for. All I knew was: keep going, keep working, keep pushing, keep showing up.
I clung tightly to the ‘workaholic’ badge like a life raft — it was my salvation, confirmation that I wasn’t drowning.
In trying my hardest not to be average, I had become exactly that. Just another rat in the rat race. Fucking pathetic. Again, I knew I had to change and raise my standards.
Lost In ‘Who Am I’
Could this, be it? Am I just a one-trick pony? How awful would it be if I’m still telling stories of that one time I was a Chief Financial Officer (CFO) at some bank or startup at a college reunion. Is this my peak?
My identity was rooted in finance and toying with working for another financial startup. At some point over the course of 2 years, it had completely taken over. I allowed it. Slowly, I forgot why I wanted to detach myself. And eventually, I just didn’t know how. Some days, I woke up lethargic and drained, without the energy to even get up. I spent those mornings just contemplating life.
How did I get there? What did I want? If this could be considered success, it certainly wasn’t all that cracked up to be. Maybe I had it all wrong — I’m young, I could let go of my ambitions and go backpacking or something. Was I unreasonable for not appreciating what I had?
I hate looking back to that part of my life, even if it was only a few years ago. I had burned out and I couldn’t even see that. It’s funny because, despite the internal turmoil, my work performance had not been affected too much. I was loyal to a fault, so I just kept at it. For my “team” and “colleagues”, I would tell myself.
It takes a moment of extraordinary clarity to walk away from someone, something, someplace that you are intrinsically attached to. It takes even greater discipline to keep moving forward and resist turning back. Especially when the road ahead remains unclear yet people still believe in your financial skillset and future role as a fiduciary.
Clarity struck me at a meeting when a colleague asked my opinion on potentially leading a joint case. I shrugged my shoulders lightly and said it didn’t matter to me, my team would be able to support whatever decision that was made. It was a somber, sobering realization: I didn’t care.
It didn’t matter whether I tried, or how much I tried. It didn’t even matter whether I excelled, whether I was highly engaged, whether I was complacent — it was simply not possible to get ahead in the lifestyle that I led. I couldn’t win; there were no victors. So, I was always adequate.
Adequate. That just wasn’t good enough — not when I wanted happiness and future success. With clarity and conviction, I stopped pursuing financial planning close to the end of 2017.
“Courage doesn’t always roar. Sometimes courage is the quiet voice at the end of the day whispering, I will try again tomorrow.”
As I’m sure most can tell, this was an interesting piece for me to write. I debated whether it was too melodramatic, yet it needed to be written and posted. Because we persist, we live and we always learn. To this day I’m still working in financial services for an insurance and technology startup in Manhattan, New York. There are more good days than bad so that’s a plus!
Nevertheless, I will always continue to keep myself busy with daily reading, financial guidance from my former rugby coach who lives and works as a fiduciary in Pittsburgh, lifting and working out with plenty of friends here in Philly, business pursuits, writing, traveling, as well as entrepreneurship as I come to the 2-year mark in owning my own business and much more. If you have a similar story, please share it with the world. Honestly, I would love to hear it and I’m sure others would too. Don’t keep it bottled up inside, that when troubles surface!
My Very Best,