Ask Before You Jump

Are you ready to take the leap into entrepreneurship?

Within a span of 24 hours, I had taken two of the biggest leaps of my life: one metaphorical, the other literal. On Friday I decided to leave behind my job as a project manager at a company I loved to pursue my own social enterprise, The following morning, I jumped out of a plane—my first time skydiving. Two huge bounds—but only one comes with a parachute.

Just as looking out the door of the airplane from 11,000 feet, the wind violently flapping your cheeks, is scary, so is being at the crossroads of your current job and your entrepreneurial passion. Eventually, though, the time comes to make sure your parachute is on tight and jump. Just as you wouldn’t leap before your parachute is in place, here are three crucial questions to ask yourself to make sure you’re ready to start your own entrepreneurial story.

  1. Do you have a support network in place? Though many have come before you, and countless will come after you, starting the entrepreneurial journey can feel quite lonely. It’s easy to imagine that no one has ever faced the kind of unique dilemmas as you. So many things felt this way for me—including trying to conquer Quickbooks—which millions of users had already figured out. Make sure you have both entrepreneurs and non-entrepreneurs with whom you can surround yourself. I found advice and comfort from talking with fellow social entrepreneurs and joining networks of like-minded innovators through programs like StartingBloc. But it was also crucial to know that my parents believed in what I was doing, to have friends willing to do whatever they could to help me succeed, a girlfriend always there to lend an ear or a shoulder, and a cofounder to be my partner in this amazing journey.
  2. Will people buy what you’re selling? Don’t let the Hollywood narrative of the overnight dotcom success story mislead you. Being a successful entrepreneur takes more than a great idea; it takes execution. For every kid in a dorm with an idea for a social network, there was still only one Mark Zuckerberg who actually made it happen. The life of an entrepreneur can be wonderful, but before you take the leap, look both ways to make sure you actually have customers. Research your target market. Run a pilot or beta test. But before you commit 100 percent to your startup, be certain that your mom isn’t the only person interested in your product.
  3. Are you ready to fail? Here’s where the skydiving metaphor ends. Failing in skydiving means death. Failing in entrepreneurship means it’s Tuesday. I’ve probably failed more since launching my venture eight months ago than I had in my entire life. The key is to let the mistakes become lessons; that’s what being an entrepreneur is all about. Failures come at all levels: From realizing you just used the word excited seven times in a two-paragraph email (guilty) to mistakes that directly impact the quality of your service to customers. The real test of entrepreneurship is how you react to these failures. And that’s what makes all the difference.

As the free fall from the plane began, I felt a rush that is hard to describe, my body hurtling toward the ground. But eventually, I the released the parachute and sailed over the hills back toward Mother Earth. As soon as I landed, I turned to my buddy and yelled, “let’s do that again!”

May your entrepreneurial leap feel the same way.


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