Styled Between Structure and Spontaneity

“Fortune befriends the bold.” – Emily Dickinson.

When I was in undergrad, I double-majored in English and Political Science, sure, no, certain that I would become a lawyer.

In my senior year I studied for the LSAT.

That summer, I received acceptances to Northwestern, George Washington, and Howard University's law schools. I was waitlisted at Columbia.

By fall, I took a gap year.

The following year, I decided I would no longer pursue law.

And it's funny, because on the entrepreneurship journey I find myself feeling very similarly to how I did then, at 21, when I chose to take that gap year. Because in that post-graduate feeling that followed, there was a lot of freedom.

There was a lot of space.

Freedom and space that I was not mentally prepared for.

It's the freedom you expect to have as an adult when you're a child. It's the freedom that comes from you having to determine the "next steps" for the first time, when before, for the first 21 years of life, there have been clear steps perfectly planned and laid out for us to follow.

Yet, entrepreneurship thrusts me back into that realm of uncertainty. It's a space where the promise of something monumental looms on the horizon, but the journey between this moment and its manifestation is fraught with space, freedom, and time. And it's in this expanse that fear or anxiety (and often both) take root, not because of its emptiness, but because of the unknown.

Some of the best advice I have ever received has come from a mentor of mine, who told me back when we worked at the same company, that the only job I had was to have fun.

This advice echoes in my entrepreneurial pursuits—the only job is to have fun.

Fun.

A seemingly simple directive, yet profoundly daunting when juxtaposed against the backdrop of a life accustomed to schedules and routines. How does one reconcile the terrors of fun when a familiar plan, when a schedule, when a routine has been the guiding force for so long?

Reflecting on my past aspiration of becoming a lawyer, I draw parallels to my current entrepreneurial odyssey. Both paths demand a courageous confrontation with the unknown, a departure from the safety net of predefined plans, and an embrace of the liberating freedom that comes with charting one's course.

Amidst the uncertainty, the essence of growth reveals itself. The interim space, the transitional period between what was and what will be, becomes a fertile ground for self-discovery and innovation. It's a canvas where the brushstrokes of aspiration redefine success on individual terms.

Until I was waitlisted at my dream school, I had wanted to be a lawyer. More school. More steps. More plans.

Until there wasn't.

Now, as I navigate the unpredictable landscape of entrepreneurship, I am reminded of that pivotal moment when I chose to deviate from the plan, from the path, from the schedule.

The realization that there are no predetermined steps, no neatly outlined plan, can be both liberating and paralyzing.

Entrepreneurship, like that gap year after college, thrusts you into the vast expanse of the unknown. It's a journey filled with ambiguity, where every decision is a step into uncharted territory. The comfort of a predefined roadmap is replaced by the need to create your own. It's an exhilarating prospect, but it comes with its own set of challenges.

The advice to "have fun" in this entrepreneurial journey is a beacon in the uncertainty. It's a reminder that amidst the chaos and unpredictability, joy and fulfillment can be found. Yet, embracing this directive can be daunting. Fun feels incongruent with the seriousness often associated with building a business. The weight of responsibility and the fear of failure can cast a shadow over the enjoyment of the process.

I grapple with this paradox often, and with these moments I am forced to reflect on the parallels between my past aspirations of becoming a lawyer and my present pursuit of entrepreneurship. Both paths demanded a willingness to confront the unknown, to step away from the safety of established plans, and to embrace the freedom, the space, the time inherent in forging one's own way.

Perhaps, in these moments of uncertainty, lies the true essence of growth. The space between what was and what will be becomes a fertile ground for self-discovery and innovation. It's a canvas where we can paint our aspirations and redefine success on our terms.

The journey of entrepreneurship is a continuous negotiation between structure and spontaneity. It's about finding the delicate balance between adhering to essential business principles and allowing creativity to flourish. The lessons learned during that gap year – the value of autonomy, adaptability, and the courage to redefine one's path – echo in my entrepreneurial endeavors.

In this space of uncertainty, I've come to appreciate the beauty of serendipity and the unforeseen opportunities that arise when we allow ourselves to explore the uncharted. Every detour becomes a lesson, every setback an opportunity to pivot and refine. The unknown, once feared, transforms into a playground of possibilities.

As I celebrate this entrepreneurial journey with the culmination of 2023, I recognize that the true fortune lies in the boldness to embrace the unknown. The freedom, the space, and the time are not adversaries but allies in the pursuit of something extraordinary. It's a reminder that sometimes, the most significant leaps are taken when we relinquish the need for a meticulously planned roadmap and simply allow ourselves to have fun in the journey of creating something uniquely ours.