How I Rebooted My Entire Career

Illustrated by Anna Sudit.
I stood in Gwyneth Paltrow's driveway, facing my biggest fear: Was I too late for my life? I was 30 years old, with a career history on a completely different track. Could I really start over now?

Let's back up.

Gwyneth Paltrow's estate marks a sort of cell service threshold in the chic and winding hills of Brentwood, Los Angeles. It's one of the wealthiest neighborhoods in L.A., yet not a single mill/billionaire has managed to install an effing cell tower. I got out of my escort's BMW, whipped out my phone, and frantically summoned an Uber.

Earlier that day, I had Uber'ed my way to a job interview at a famous director's Brentwood mansion. He and his producer wife were searching for a development exec. I'd nailed the interview, but when it came time to leave I awkwardly confessed that I couldn't get a return Uber due to lack of reception. The director's wife sympathetically offered to drive me to the Paltrow Service Portal. During the short trip, she all but told me I got the gig.

At this juncture, most people would do a victory dance on Gwyneth's gravel. Instead, I was terrified. It was a dream job with one hitch: it wasn't my dream.

After years in development back in New York, I'd recently moved to Los Angeles to pursue my actual dream: becoming a TV writer. I had made significant strides toward this goal: securing representation and packaging a pilot. These were positive steps, but nothing was paying yet. A serious problem when you're B.A.F. (Broke As Fuck).

So, I stood in Gwyn's driveway, considering my two possible paths. It was not unlike her Miramax-era cheese soufflé Sliding Doors: Was I going to be brunette Gwyneth and stay in my miserable career? Or, would I be blonde Gwyneth, turn down this easy money, and struggle to achieve my dreams (albeit sporting a modified pixie cut with questionably flowered Ren Faire braids)?

But, I wasn't in a position to settle. Last summer, Fate showed up knocked on my door and announced that I had won the Fuck-Me Sweepstakes, complete with a devastating breakup, job loss, and testicular cancer. Fortunately, I survived it all. And, dodging death puts life into new perspective. I'd moved to L.A. to chase my true passion, no matter how hard the struggle. I had to turn the money gig down. Blonde Gwyneth it is.

Struggle is often the first thing subtracted from success stories. But, look behind most "overnight" triumphs, and you'll find years of failure. No one knows this better than Gillian Zoe Segal, author of Getting There: A Book of Mentors. In her book, major visionaries share first person accounts of their struggles toward success. Matthew Weiner, Jeff Koons, Rachel Zoe, Anderson Cooper (you get the idea): Getting There's table of contents reads like the seating chart for Michelle Obama's next dinner party.

I spoke with Segal about the wisdom she gleaned from these luminaries, and our conversation was a helpful reminder that careers can be made at any age. If you ignore the latest listicle of "Top 5 Entrepreneurs Under The Age Of 5," you can pay attention to something much more valuable: yourself.

I know — it's easier said than done. So, for those moments when the universe tells you to quit, here's how to tell the universe to suck it.

More from Work & Money