'Do More of What You Enjoy' and Other Lessons I've Learned Starting My Own Business

If you want to make the jump, but you're fearful about what's going to happen, just know that it's both natural and also completely irrational.
04/18/2016 02:09 pm ET Updated Apr 19, 2017

When to Jump is a curated community featuring the ideas and stories of people who have made the decision to leave something comfortable and chase a passion.

If you want to make the jump, but you're fearful about what's going to happen, just know that it's both natural and also completely irrational. That's a little both-and philosophy for you--a type of logic in decision making where you choose both. Like a family member or friend that annoys the crap out of you, but whom you still love unconditionally. It's clearly different than either-or logic, where you must fall to one side or the other in making a decision.

The world operates on both logic systems. I'd prefer a precise mode of thinking when it comes to flying airplanes and a more abstract approach when it comes to reflecting on my passions. Embracing ambiguity and both-and thinking helped me to make my jump--starting a psychedelic activewear company--for three reasons:

1. I was less fearful when I saw that making the jump didn't boil down to passion vs. stability.

Two and a half years ago, I carried around an enormous amount of anxiety because I wanted to do something creative but couldn't fathom leaving my stable job in finance. How would I pay the rent? Eat out at two and three dollar sign restaurants at Yelp? Date? But I was viewing the world in black and white, through a lens of extremes. Is it truly plausible that the vast majority of people who pursue their passions end up penniless?

My anxiety slowly subsided when I read biographies of people who did their own thing. Most creatives, entrepreneurs, and others who go on their own path faced this problem of an initial decrease in cash flow. When I peeled back the layers of this supposed dichotomy, I realized it was a solvable problem, not a choice between two extremes.

2. I was forced to be creative in attaining stability.

By working under the philosophy of both-and, I assumed that pursuing my passion and attaining some level of stability were both possible. But I had to get creative to make it happen. I moved to a cheaper apartment, prepared food at home, and rented out a spare room on Airbnb. I researched ways of receiving unemployment benefits (New York has a great program called SEAP that helps those who want to start their own company).

It still can be difficult at times, but it works. You have to get creative, you have to hustle, and you have to make sacrifices. But if you truly want to make the jump, that's a very small price to pay. So work from the assumption that supporting yourself is entirely within the realm of possibility. Then Google the crap out of "how to save money" and "how to have side income."

3. There is no right path, so I might as well investigate the ones I like.

Starting a clothing company is thrilling and horrifying; I bear full responsibility for its success and failure. Working for a corporation is stable and risky; the paycheck is always there until the company needs to downsize to maximize shareholder return. Traveling the world is liberating and lonely; freedom comes at the price of maintaining relationships. As I began to operate under the philosophy of both-and, I started to see that every choice and every path comes with the good and the bad.

So I decided to try doing the things I enjoyed.

And I think that's the real key. More than any system of logic or framework or textbook advice, I'd say follow that basic concept: do more of what you enjoy. It doesn't have to be a big jump, it can just be a hobby, or an extracurricular. Take the time to think deeply about what piques your interest. Maybe you stayed longer at the rock climbing gym than you thought you would, or you can't ever seem to stop reading about artificial intelligence. Making the jump doesn't mean you have to quit your job and climb Machu Picchu--to me, it means that you're exploring the things you enjoy doing. And ultimately, in making a jump, that's what counts the most.

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