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"These are the times that try men's souls."

I can think of no other way to describe my friend's situation than to steal from Thomas Paine. May he forgive me. And may my friend -- whom I'll call "Tom" in honor of Mr. Paine -- have the courage of his new namesake.

My friend Tom is the kind of person who sends me stuff like this recent piece in USA Today about how it's okay to fail as many times are necessary to succeed if you're doing what you really love -- in this case, entrepreneurship.

• P.T. Barnum filed for bankruptcy, and then he started his circus.

• John Henry Heinz's company filed for bankruptcy in 1875. The next year he invented a nice little condiment — known as ketchup.

• Henry Ford's first car company filed for bankruptcy, and his second car company failed. His third business was the Ford Motor Company.

Lots of people are inspired by the entrepreneurial spirit, but even when they stumble upon an as-good-as-it-gets opportunity, they back down. I'd say that, given the opportunity, Tom is more likely than most to not back down, to stand up and take a shot at the dream. Well, we're going to see what happens this first time around...

Tom will soon graduate from college, and it's high time he decides what's next. Of course, he can do anything. The possibilities are infinite, as they are for you, me, and everyone else. But when Tom cut through the BS in a recent conversation, he revealed the two final options. Will he...

(A) take a highly coveted position in a company everyone is in love with? Pros: Interesting work, hefty starting salary, smart colleagues that work hard and play hard, no risk because they company is kicking butt, and congratulations/admiration from everyone he meets for being on the "fast track." Cons: He might end up thinking "I wish I were one of the founders" more than thinking about his work.

OR

(B) become the second team member of a start-up technology company you probably haven't heard of? Pros: Technology development is already good and done and just waiting for someone to be a sales/marketing wizard to generate buzz for the company and cash out through an acquisition, Tom would make a pretty penny from his stock at the sale, chance to drink from the firehose and test everything he believes about himself, and chance to altogether skip the sick game that is "the fast track." (2 important pros I forgot to include initially: Tom has no debt from college, and it's likely that he could cover his living expenses with his salary from this start-up.) Cons: He could fail and be sad that he passed up option (A), which was completely safe.

I won't speculate upon what I would do or what Tom "should" do, but I will share two predictions:

1. If Tom's true to the rhetoric he spews (no way of knowing if this is the same as being true to himself), I think he'll choose option (B). And it will be seen as a very bold move by everyone, even if it seems very natural to Tom.

2. If Tom takes option (A), no one will bat an eye. Though I'll wonder if he's happy with the decision.

Still, I know that Tom will have to go through hell to choose option (B) -- the start-up. As much as he can say he embraces failure and point to stories about great entrepreneurs or other great ones from all walks of life and how they had their share of failures, he still doesn't want to fail. No one does.

But Tom's fear of failure is really strong, because he hasn't failed yet. I haven't either. Chances are that you, too, haven't failed. Sure, we've failed to do little stuff, like writing a good-enough paper that still got an "A" instead of writing the exceptional paper we knew we had in us. We've fallen a bit short of major goals of ours. I didn't win a state wrestling championship in high school. I won third and fourth place medals. You may have not been admitted to Harvard; instead, you went to Northwestern. Darn.

I'm talking about really "failing." I'm talking about stuff old women and newspapers gossip about like dissolving companies, going bankrupt, getting divorced, and going to jail.

If you graduate from high school and you graduate from college, you're sparkling in our society. And then there's this huge pressure to not fail and just keep building your pedigree. For what reason, I don't know. Putting one more well-respected, well-known name on your resume might make it easier to get hired in five years by someone who has the same name on her resume. But it won't make you happier. It won't get your butt out of bed in the morning.

It's not what we did in the past that lights our fires. It's what we do now, and what we do next.

I'm excited for Tom, because however difficult a decision he's making, he's exactly where he has long dreamed of being. And if, in fact, his heart and gut tell him to go run the start-up and he goes for it (even if he ends up failing!), he's going to feel what so many people never feel -- the greatness of chasing your dream, even if everyone else thinks you're crazy.

Posted by Ian Ybarra on 25 May 2005

Comments

Posted by: Neville Medhora at May 27, 2005 04:14 AM

Posted by: Michelle at May 27, 2005 01:05 PM

Posted by: Cap at May 27, 2005 06:26 PM

Posted by: Matt at May 28, 2005 04:16 AM

Posted by: Ian Ybarra at May 28, 2005 09:08 AM