Being My Boss – A reflection

December 11th, 2006 • To be filed

I’ve recieved many emails from you about the Being My Boss series. My original intent was to publish 101 interviews with entrepreneurs and stop there but after 10 amazing interviews, I don’t think I ever want to stop. Speaking with these people, has been incredibly uplifting and gives me a strong sense of purpose as I continue hunting for stronger stories and entrepreneurs.

The idea of working for oneself, and being happy doing it is incredibly enchanting. Just this morning on my way to work my cab-driver stuck up a conversation with me. It was early and I was still slightly groggy from staying up late last night to finish Season 4 of 24 (my newest addiction) But when someone so willingly opens themselves to you, your only choice is to sit up and listen. My driver was 47 years old and had just quit his job as a leaking specialist with a manufacturer or large vaccum furances. A job he lucked into because even though he had a full scholarship to an esteemed college in Philadelphia, he dropped out after 6 months because he just wasn’t comfortable in teh company of rich, privileged kids.

I asked him if he was in-between jobs and he hesitated a little before admitting that he’s never been happier and quitting that job has allowed him to pick up on educating himself. He doesn’t know how to use a computer and ‘I’m too poor to own one," but "I know how to use the catalog computers at the library," he said. His voice lilted with pride when he said he was learning everything he could about cognitive sciences and brushing him his literature. As we turned onto the curb, he quietly mentioned that he wants to be a writer and now he has the time. So heartfelt. I could only give him a fat tip but if I was a millionaire, I’d have bought him a computer. It is stories like these… I don’t know if he’ll grow to become the next Gladwell. But I do know that some of us spend a lifetime not realizing that quitting someone else’s dream to follow your own is what it takes to find contentment and happy-ness.

This guy, was happy. So happy that he felt the need to spread the gospel about his new life to random strangers who perhaps wouldn’t judge him and would share his pride.

I looked at all our Linkedin profiles and realize that it’s not who we are that defines us, it’s what we do. Our profession, our affiliations, those ivy league schools, THE job…..and if what we do will define us, why not do something we believe in?

I think there’s an entrepreneur within each of us, only a matter of bringing him/her out. One of you asked if it’s easy to approach these entrepreneurs and have them agree to do an interview. My answer – you’ll be surprised.

It never is easy, from what I hear. From managing personal relationships to the business, weighing choices between spending more time with the kids or flying cross-country to seal the deal, being your own boss is perhaps the most difficult job. So far, I end my interviews by asking "What’s the best thing about being your own boss,?" Begining today, I’ve added one more question, "What’s the worst thing about being your own boss?" I didn’t want to protray the grit of it initially but with almost 10 stories down, we are well-aware being your own boss has some wonderful merits. The time now, is right for the second side of the coin to be rightfully displayed.

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