Mitt Romney and Conan O’Brien Revel in Their Unemployment

by Greg Pollowitz

I’m sure there will be Romney defenders who say this is no big deal, but when a multi-millionaire jokes with an audience the he is “also unemployed” is an issue for me. It’s just politically stupid.

Another, and more annoying to me, figure playing up his recent bout of unemployment was Conan O’Brien while giving the commencement address at Dartmouth College.

I’ll admit, most of it was quite funny but I didn’t like his ending — his real message to the class of 2011. O’Brien goes on to tell how his dream had always been to host the Tonight Show. And when that dream disappeared, thanks to Jay Leno, he hold the graduates:

Now, by definition, Commencement speakers at an Ivy League college are considered successful. But a little over a year ago, I experienced a profound and very public disappointment. I did not get what I wanted, and I left a system that had nurtured and helped define me for the better part of 17 years. I went from being in the center of the grid to not only off the grid, but underneath the coffee table that the grid sits on, lost in the shag carpeting that is underneath the coffee table supporting the grid. It was the making of a career disaster, and a terrible analogy.

But then something spectacular happened. Fogbound, with no compass, and adrift, I started trying things. I grew a strange, cinnamon beard. I dove into the world of social media. I started tweeting my comedy. I threw together a national tour. I played the guitar. I did stand-up, wore a skin-tight blue leather suit, recorded an album, made a documentary, and frightened my friends and family. Ultimately, I abandoned all preconceived perceptions of my career path and stature and took a job on basic cable with a network most famous for showing reruns, along with sitcoms created by a tall, black man who dresses like an old, black woman. I did a lot of silly, unconventional, spontaneous and seemingly irrational things and guess what: with the exception of the blue leather suit, it was the most satisfying and fascinating year of my professional life. To this day I still don’t understand exactly what happened, but I have never had more fun, been more challenged—and this is important—had more conviction about what I was doing.

How could this be true? Well, it’s simple: There are few things more liberating in this life than having your worst fear realized. I went to college with many people who prided themselves on knowing exactly who they were and exactly where they were going. At Harvard, five different guys in my class told me that they would one day be President of the United States. Four of them were later killed in motel shoot-outs. The other one briefly hosted Blues Clues, before dying senselessly in yet another motel shoot-out. Your path at 22 will not necessarily be your path at 32 or 42. One’s dream is constantly evolving, rising and falling, changing course. This happens in every job, but because I have worked in comedy for twenty-five years, I can probably speak best about my own profession.

His message made sense: what your dreams are at 22 will be different at 32, 42, etc., but I suspect O’Brien’s life-crushing loss of his dream job and his time “adrift” was made somewhat easier thanks to ginormous size of his savings account.

Let me reiterate, O’Brien’s message was spot on, but it would have been better delivered by someone whose had to make some financial concessions as he chose the next path in his life.

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