What I’ve Learned From Risking it All by Taking a Chance on My Dreams

It’s another late night at work. Same old story: The girlfriend is at home and probably frustrated with me, again.

I hadn’t a clue what I was getting myself into when I became a business owner five years ago. The voice in my head wouldn’t stop pounding on my heart. It pushed me in this direction, whether I was ready or not (I wasn’t). Still, I jumped in, and there was no turning back. I pushed all my chips into the pot, cut the ropes behind me and started a restaurant 500 miles from home.

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I had fantasized about owning a restaurant since I was 11 years old. Suddenly, I was 28, and all those years of reverie had come to life. Two months later, I started my second business. Now, I was an entrepreneur. It would be nice if that was the end of the story, but it’s not. A few months later, my second business failed.

Entrepreneurs bring ideas to life in the form of products and services. Executing those ideas often deter most from giving it a shot. From gauging market conditions, to creating company culture, to marketing, product development and more, an entrepreneur’s to-do list is long. Still, we see potential and fundamentally believe that our idea can make the world a better place— so we take a chance. We risk our relationships, finances, pride and often our health, to bring the idea to life. We see it through, and do everything to make it work.

The world doesn't tell us how rewards come in a variety of flavors.

Hell, it’s risky, but potential rewards lurk on the other side. Unfortunately, the world doesn’t tell us how rewards come in a variety of flavors. Financial gain is just one reward of many. Sure, a successful business can provide financial well-being, and a comfortable life — but we can also have that while reporting to a boss and working a nine-to-five. Being an entrepreneuer has given me a different perspective: I see both wins and losses as lessons learned, and I see setbacks as another chance to get back in the game.

The ultimate goal shouldn’t be financial payoff — that’s a losing game. It’s losing, because once you start chasing it, you’ll never have enough and will always want more.

Most businesses fail. Failure leaves two choices: Pack your bags, call it a day, and pat yourself on the back for giving it a shot; or, you can ask yourself what can be learned from this. The latter mentality doesn’t pay the bills, and it won’t keep your spouse off your back, but it results in more knowledge for the next time around. As the brilliant marketer and entrepreneur Seth Godin says: "If I fail more than you do, I win, because built into that lesson is the notion that you get to keep playing. If you get to keep playing, sooner or later, you’re going to make it succeed. The people who lose are the ones who don’t fail at all, and get stuck, or are the ones who fail so big that they don’t get to play again."

I've learned, through experience, that in order to find the path to success, you must try different paths that don’t work. That's what it means to be an entrepreneur: Try and fail. Rinse and repeat. As Godin hints, we can earn just about anything back — everything except time. All over the world, the same story runs through the minds of men and women, who are on their deathbeds. The narrative is ridden with regret and the chances they could have taken. "What if?" is asked over and over.

Taking chances involves risk.

It also involves doing something that matters and is important to you. There is much pride in taking the shot— knowing you could have watched from the sidelines with everyone else. Entrepreneurship has taught me a lot of things, but most importantly this: It is supposed to be hard. That's what makes it meaningful. That’s what makes me feel alive.

How does that Kelly Clarkson song go, “What doesn’t kill you makes you stronger”?

I’ve won. I’ve lost. I’ve learned. I’ve been made stronger. My next restaurant is still on the horizon somewhere. It could fail and that’s okay. I will keep playing this game — it’s a fun one. And even if I fail, it’s better than sitting on the sidelines.

— CHRIS HILL

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