As kids, my father often told us “We may not be the smartest, but we’re the hardest working.” As an awkward and shy fourteen year old, I took those words to heart and taught myself how to design web pages. I learned how to hustle, well before Rick Ross glamorized the virtue. This work ethic carried me over into my finance career, where I was promoted to Managing Director at 31. This had to be the culmination point. And it felt really damn good, until I realized that the only person who cared about my new title was my mom (who physically collected all of my business cards and taped them to her desk). Two months later as the high wore off and the grind resumed, my rocket ship came back down to earth. I still couldn’t be present in front of my wife and little girl, the two people I love the most. That deeper sense of purpose and meaning were still absent. And those deeper fears, anxieties, and insecurities — many of those traceable back to my fourteen year old self — were still part of my daily being, Managing Director or Not.
So I quit. (Well, three years later.) Initially, I thought that the missing piece of fulfillment was entrepreneurship. After all, being a founder is glamorized as the silver bullet for those trying to find meaning. But I quickly realized that this desire was the continuation of a lifelong behavior that held me back. I had always asked a lot of little questions, but never created the space to ask a few big questions. What change do I want to see in the world? What’s my personal definition of success?
It sounds so straightforward, but it’s not. Because when you ask those questions, those fears, anxieties, and insecurities come racing back to the surface. Our egos default to traditional markers of success, external benchmarks such as money, recognition, or appearances. And we’re taught our entire lives to repress, contain, and ignore our fears. But like our shadow, we can’t outrun them or contain them. We must learn to just be still with them.
And ironically, that is where I found my joy. I never was much of writer in my life, my language was numbers and computers. But I became determined to attempt the age old question, “What does it mean to live a whole life?” A question that has vexed humankind since the beginning of time and has birthed scholars such as Lao Tzu, Marie Curie, and DJ Khaled. I applied the rigor from my investing career to explore and synthesize the teachings from fields including positive psychology, sports science, religion, pop culture, and self-help.
But the floodgates opened when I gave myself permission to share both vulnerably and authentically. This ran counter to my fourteen year career in finance, where the prevailing culture is one of “wearing a mask.” I initially told these personal stories on my blog RadReads and now write regularly about self-knowledge, career, and relationships, as Quartz’s Entrepreneur-in-Residence.
And I’ve come to realize that happiness, just like physical fitness, is a daily practice with no end goal. I used to treat happiness as the residual or the left-overs of my daily corporate hustle. But now, I’ve set clear intentions — prioritizing family, creating the space for deep introspection, building a community centered around compassion, and continuing to share authentically. That’s my practice.
Originally published at medium.com