This past weekend, I hung out with a terrific couple: a Shakespeare professor and an Art History professor, both in their 60s, both very successful. They have a beautiful home, great careers, an intellectually stimulating life, and disposable cash. They bet their livelihood on their own creative minds and they won. They are happy, healthy, and completely set for retirement.
I was undone by them.
When they were in their twenties, they chose career paths.
When I was in my twenties, I avoided choosing a career path as though it would give me an intestinal infection. I lived paycheck to paycheck. I never got ahead. It was uncomfortable, but I fooled myself into thinking it was better to live on hot dogs for a week than “sell out.” I wanted to be a wildly successful artist, and if I couldn’t be that, I’d be a starving artist, which had its own glamour. New York supported that choice. My actor and journalist roommates supported that choice. We didn’t want to slave, we wanted to LIVE.
But the truth was that I was a slave. I was a slave to my two-week paycheck. I was a slave to my “short-term-solution” job. I was doing nothing to empower myself for the long haul.
This is what I did in my twenties. This was my career track:
• Assistant editor at Departures magazine
• Flee to Mexico, live off credit card, buy 100 mesh bags to start “boutique bag business” with roommate, which consisted of playing Manu Chao music outside of apartment on a piece of blue Astroturf with bags on clothesline
• Sell 80 bags, become daunted by what it would actually take to run a business
• Waitress at sushi restaurant and local bar
• Boyfriend at the time says I would enjoy the intellectual challenge of working in a high-powered law firm as a paralegal; I agree to do it; I work for three years, averaging 4 hours of sleep a night, everyone else I’m working with is intending to go to law school, I could give a shit about law school, eventually resign because am exhausted
• Begin temping as a legal assistant and go back to cocktail waitressing at local bar
• Start a writers’ group that ends up being covered on ABC News, but never get my novel finished
• While waitressing at local bar, interview characters with roommate that will eventually become a play about the gentrification of our neighborhood in Brooklyn; the play is a success and garners two stories in The New York Times, I get a literary agent and two TV agents out of this
• Think fame will just come knocking at my door and so live off credit cards waiting for knock. Fame does not come.
• Crawl back to temping at law firm for same people who thought I was going to become famous
• Take job as assistant to head of Lower East Side Tenement Museum
• Stay at Museum nearly three years, start own freelance business which is a hodgepodge of 1) running a dialogue series on the Israeli-Palestinian conflict; 2) helping produce a series of launch parties for a German multimedia event called TRIP; 3) transcribing reality show transcripts for VH1; 4) writing about CFOs of independent schools for an association based in Boulder
• Take a “month off” to visit Boulder, end up falling in love here and keeping CFO gig as sole client
This looks like the resume of a schizophrenic person! It’s a resume of beginnings and loose ends. It’s not a resume I can walk into a “real” career job with. I picked up terrific skills along the way, but I’m still carrying them in a basket, and I don’t know where to set it down.
However, it’s also a resume of stories. And there are great stories in there. There were awesome moments, phenomenal friendships, incredible experiences, and fabulous Friday nights. In so many ways, I LOVED my twenties in New York.
But they came with a price. I am just now realizing the price, and it is sobering as hell.
Did I waste my twenties?