Making The Decision to Explore On My Own

I distinctly remember staring into the mirror at age 15, wondering what life would be like in ten years. What type of career did I choose? Was I happy with my job? What city am I living in? There were so many unknowns. I had no idea what the next ten years would bring and how they would shape my life.

I remember that moment like it was yesterday, and here I am – 12 years later – wondering what 15-year old Steve would think about how things ended up. Would he be proud? Disappointed? I’m still not sure of the answer. However, he’d certainly be surprised to discover that five years into my working career, I’d make the decision to leave my job without anything lined up.

So why this? And why now?

Looking back at my career, I made two critical decisions which led me to where I am today:

1. For my first job, I spent ten months as an Investment Banking Analyst at Moelis. There, I learned the importance of doing work that makes you happy, so I left early in search of a job that would bring me happiness.
2. In my second job, I spent 2.5 years as a Product Manager at Scopely. During my time at Scopely, I realized that there’s more to life than just being happy, so I eventually left in search of an opportunity that would bring me fulfillment.

My search for fulfillment ultimately led me to San Francisco, where I joined Ever, an early-stage productivity startup. We were a small, scrappy team that was super passionate about helping people rediscover their life’s memories and I took that mission to heart. We tried a ton of things over the following year but despite our best efforts, Ever didn’t work out the way we wanted and the company had to pivot.

The pivot signaled an end to another chapter in my career, but this time I was at peace with the outcome. My experience at Ever taught me first-hand that the benefits of pursuing a fulfilling life existed both in doing fulfilling work and also in embracing the journey it takes to get there. Sometimes things don’t work out, and that’s okay. Life has many uncertainties, but I’ve found the greatest joy and peace of mind in being true to the process of finding my loves and testing my loves. To me, this is living a fulfilling life.

After Ever, I moved to a Founder-in-Residence role at Atomic Labs, the venture studio that incubated Ever. I stayed for ten months before transitioning out of Atomic to explore new ideas and projects on my own, a decision based on something that felt right in my heart and I decided to run with it.

Steve Jobs describes this process of decision making, saying:

You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something - your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life

I left without another job waiting because it was the ultimate unexplored dot – an experience I thought would never become part of my story but became more and more of a reality with each passing month, as I increasingly desired freedom of exploration and discovery. Eventually, by the end of my time at Atomic, it seemed like the only logical choice I could make.

More than anything, I wanted to discover where I would end up if I were entirely on my own, without any job or responsibilities. With all the time in the world, where would my interests, skills, passions and curiosities guide me? I’m fortunate to be able to support myself temporarily without a paycheck, and I want to make the most of this opportunity. I’m hoping to start by spending more time reading, traveling, meeting new people and exploring my curiosities about how the world works and how technology can help people live better lives.

I’ll be the first to admit that I’m nervous, scared and excited all at the same time, but I’m trusting my heart on this one. I have no idea where this journey will lead, but I can’t wait to look back and see how this dot ends up connecting with the rest in the future.

As I embark on this next chapter of my life, I’m reminded of the following words by F. Scott Fitzgerald:

For what it’s worth: it’s never too late or, in my case, too early to be whoever you want to be. There’s no time limit, stop whenever you want. You can change or stay the same, there are no rules to this thing. We can make the best or the worst of it. I hope you make the best of it. And I hope you see things that startle you. I hope you feel things you never felt before. I hope you meet people with a different point of view. I hope you live a life you’re proud of. If you find that you’re not, I hope you have the courage to start all over again

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