I’ve Pivoted My Career So Much, I’m Pirouetting

In August 2014, I lost my freelancing job as the Director of Content at Grey, a global, 100-year-old advertising agency, often referenced in Mad Men. (It’s where Duck Phillips landed after being dumped by Sterling Cooper.) Because Grey slashed my short-lived position, a frequent mini-tragedy at ad agencies, I was searching for a new full-time gig. I became obsessed with joining one of the bright, shiny digital media start-ups in New York City, partly out of fear that if I didn’t work at a hot, tech-based company, I would soon become a dinosaur. I had studied journalism, and traditional media were on life support. As a Gen-Xer, I felt that my professional currency was quickly fading and I needed to switch gears so I could sparkle…or, at the very least, find a job.

I interviewed at a small hybrid PR/social media agency where a dozen under-30-somethings sat shoulder-to-shoulder on ergonomic chairs, huddled around an eco-friendly, reclaimed oak table. Macs lit up the room as an Irish Setter meandered down the narrow aisles, looking to be scratched. In a makeshift meeting room, the bearded Millennial interviewing me studied my resume on his laptop, refusing its paper version on ethical grounds.

“We like to save trees around here,” he said. I smiled and shoved my offensive wad of resumes and bios back into my bag. Old school, I invariably carry multiple hard copies to interviews.

“I see that you were a press secretary on Capitol Hill,” he began.

“Yes!” I exclaimed, excited that the hipster noticed one of my first jobs out of college. While in my early 20s, I worked for two Democratic members of Congress during the Clinton administration, jobs that I always thought were impressive and important.

“Well, the way we operate here is that we have good relationships with the media,” the Millennial sniffed. “Relationships are everything. It concerns me that you worked in politics. I mean, I wouldn’t want you slamming down the phone and pissing people off.”


Until now, my political experience had opened doors and given me a certain gravitas and credibility. The Hill was the Google of the Gen X generation, paving the way for big-time careers. After Capitol Hill, I worked at Dateline NBC, Fox and CNN. I’ve had a smorgasbord of interesting jobs, but this guy was put off by my political background from the mid-1990s.

“I’m not a character in Veep or House of Cards,” I said cheerfully. “I started as a 22-year-old working for a freshman congressman from Miami in a super crowded media market. I was begging reporters to cover us. I wasn’t hanging up on anyone.”

In a makeshift meeting room, the bearded Millennial interviewing me studied my resume on his laptop, refusing its paper version on ethical grounds.

As I slunk out the door, after grabbing a handful of kale chips and a coconut water, I realized that this struck at a bigger issue. I, a solid Gen-Xer, who came of age during Walkmans and the birth of Diet Coke, was more culturally disconnected from this Millennial than I had imagined. Now, walking down Fifth Avenue, I realized that my personal career pivot was going to be harder than I expected.  I needed to hone my story. I needed to re-package my narrative.

I needed to own my experience but re-position my pitch. I might even need to take a big pay cut and move backward before I could move forward again.

Big trends have a way of touching all of us. From tattoos to Birkenstocks to gay marriage, certain ideas, products and political movements have an uncanny ability to reach critical mass and then gain acceptance, folding into the fabric of our collective culture. Today, Silicon Valley is our cultural crush. It’s part mythology with its unicorns and part psychology with its change-the-world, disrupt-the-status quo, always-innovating ethos.

The celebrated start-up model of disruption that embraces failing fast and pivoting is not a typically female one. Women tend to be more risk-averse. We can over think our next move and not act until we’re 100 percent ready. We may feel like a fraud when we’re trying something new. Instead of being disruptive, women tend to be more disciplined. And we’re often not pivoting because we feel stuck.

So what if women embraced the start-up model? What if we had the confidence to take risks, even if we knew we might fail first? What if, instead of agonizing about which step to take, we leapt forward quickly? What if we could apply the lessons of iteration, engineering serendipity, failing fast, networking and strategic branding to help us redirect our path or transform our careers?

No surprise, but I never got the job at that startup media agency. And that depressing interview was followed by a few more increasingly frustrating ones. It seemed that every person who interviewed me during that chunk of time at the end of 2014 had graduated from college in 2009. That would make them 27 years old. I was 43.

Channeling Nora Ephron and her mantra that “everything is copy,” all of these experiences led me to write Fearless and Free: How Smart Women Pivot and Relaunch their Careers.

I say that I’ve pivoted so much that I’m pirouetting, and if I hadn’t “failed” as many times as I have, I would have never written this book or felt as fearless and free as I do.

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