Feel-Good Fridays: On What Entrepreneurship Really is

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Hey folks. How’s your week been? How’s your month been turning out so far?

Let me tell you, guys: 2013 is shaping up to be, perhaps, the first year since just after college where I have absolutely no idea what the next 12 months have in store for me. It’s simultaneously liberating and intimidating, and I’m sure you can relate.

In the two years Inc. Well has existed, I’ve gone from co-running it with the very lovely and talented Carlise Newman and realizing that I, too, was an entrepreneur as a freelance writer to being completely enmeshed in the startup culture and community. Having 1871 as a home base helps reinforce that on a daily basis.

I’ve noticed, too, that in my clique here (which includes fellow Inc. Well blogger Jill Salzman) and many new, great friends that there can be a tendency to sometimes get discouraged about the trajectory of your career.

I’m here to tell you that this is completely, completely normal. This is pretty snooty of me to quote, I suppose, but Aaron Sorkin said this in a 2012 Syracuse University commencement speech: “Develop your own compass, and trust it. Take risks, dare to fail, remember the first person through the wall always gets hurt.”

It’s that last part I think we so often forget: “The first person through the wall always gets hurt.”

And from there, what distinguishes us is how we deal with getting hurt. Do you stay down and give up? Or do you dust yourself and press on?

I was talking to Salzman this week about a meeting I had that went surprisingly well — I mean, I was expecting it to go well, but it blew me away with the possibilities it would yield. When you’re an entrepreneur, though, you are conditioned to sort of not believe things are going to go through until you sign the contracts or see that first check.

I said, “It’s both exciting and daunting — specially with bills to pay.” Jill said, “Totally. But that’s true entrepreneurship, which just means ‘ass broke and optimistic.’”

I responded, “I prefer to think of it as arrogantly betting on your success against all odds.”

And so, as we are about to wander off into another weekend, I just wanted to drop in your ears this: Keep betting on yourself. It’ll pay off eventually. Take solace in the support and comfort your friends and family give you — and definitely savor the successes you have as they are meted out.


Feel-Good Fridays is a new thing I'm trying out. If you have a nugget you want to share to encourage other entrepreneurs with, give me a shout on Twitter.

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.

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