How I Know I Will Be A Successful Entrepreneur

04.11.11 | 7 notes | Bob DylanJean GiraudouxKatie CouricSteve Jobsmediocrerejectionwidgetsminutiae

I used to be afraid of not having job security, not having a regular paycheck, not saving for retirement. Now I’m more afraid of gnawing my teeth off by working for the man for the next 30 years. I used to feel that not appreciating a “good job” made me an ungrateful Generation X-er, that my parents and grandparents settled for less, stuck with jobs for decades, so I should hunker down and work for the man. But, then I realized that society is wrong for making us feel like searching for more means we’re lost. Maybe we are just searching for more. Maybe there would be no vaccines, no iPhone, no Internet, without people that were scared of the mediocre. Maybe that makes me a snob. I don’t care. I’m liberated by the recent revelation that I don’t care what people think of me. I care if I respect myself and do good work. I respect myself for wanting something bigger and not just for the money, which buys freedom, but also for the goals and potential impact a bigger goal could have on the world.

You can’t please everyone, and you can’t make everyone like you - Katie Couric

I think I thought moving back to Boston would change things. I expected too much from Boston. But after the disappointment, the longing for NYC, the acceptance that most people I know in Boston live inside the “American Dream,” I realized that the life I’m experiencing now is what I needed to realize that I’m ready to acknowledge that the American Dream is dead and even if it weren’t, I wouldn’t want for it. Because if I have to live alone in a rental, drive a 15 year old car, and eat frozen vegetables for 10 years to find that big idea that will sell, for which I’ll be able to afford freedom and travel, then I’ll do it. 

In America, we are programmed to think there is a right way to live—high school, college, job your parents can brag about, marriage, baby, bigger house, minivan, kids go to college, etc. All of that must come to avoid the pity look and it all must come in that order. And yet all of that often comes with adultery, divorce, and debt.

All the truth in the world adds up to one big lie. - Bob Dylan

Recently I’ve become tired of people telling me I’m single because I’m picky, that doing my job isn’t deserving of a thank you more than once a year, that we should all be happy to belabor the minutia at work when there are so many things going on in the world, when the minutiae is really not worth our time when considering the bigger picture. But I guess that’s when I realized I no longer want to avoid discomfort or fear or ignorance.

Only the mediocre are always at their best - Jean Giraudoux

If you’ve reached a point in your life where there’s no personal struggle, no angst, no yearning for more hours in the day, no a-ha moments, then you’re complacent. Quite frankly I was never OK with being another normal but now I’m just strong enough to say it. Imperfect and constantly growing personally and professionally yes, but normal or average, no. But maybe that’s just all in the perception.

Working for an organization in a seemingly stable, comfortable job is worthy of respect. In the end, most of us are making widgets, whether tangible or not. Maybe not the President but even Steve Jobs, he made widgets. Widgets that were highly valued and that changed the way we consume media, but widgets nonetheless. And we need people to keep making these widgets—I just want to create a new widget and hire others to make them. Is there something wrong with that?

I’ve been rejected by probably 100 companies, about four men I was in love with, and many former friends - because maybe I wasn’t right for them. And that’s OK because maybe it wasn’t going to be a lasting match and other opportunities and loves surfaced, ones from which I was able to grow and learn. Companies, men, and women have the right to say ‘no’ I’m looking for a better match. One day when I was living on East 23rd street in NYC, I got rejected for three different jobs, by phone, snail mail, and email. I just laughed. What else could I do?