“I spent the first 28 years of my life as a f**k up and a failure"

Jennifer Romolini’s media career has been impressive, but before her success at Yahoo and other companies, she moved to New York as a self-proclaimed “awkward 27-year-old misfit,” the skinny, long-limbed daughter of a working-class Philadelphia couple. Her new book, "Weird in a World That’s Not," which is part memoir and part career guide, begins, “I am not supposed to be here. I spent the first 28 years of my life as a fuckup and a failure. I failed and I failed and I failed.”

How did she get to the point where she wrote a book about professional success? Through one struggle after another.

“I had a miscarriage at four and a half months — a week before my wedding — and I went through with the wedding anyway, even though I knew I shouldn't,” she told me on "The Lonely Hour."

“We stayed married for three years. We moved around quite a bit because he was a hotel manager and he worked in different hotels, some of which we lived in. The night that I decided to leave him, I decided that I was going to start to really get control of my life.”

She had to find herself, and then trust herself.

“I wasn't refined. I still had this lingering Philly accent, and I just had not hung out in the worlds that everybody else had seemed to hang out in. But the adventure was thrilling to me, and I think that was enough. I rented a U-Haul that I had to drive from Boston to New York and it was fucking terrifying; I had to stop every half hour because I was having panic attacks."

But I got that truck to New York and I unpacked my shit, and then I sat in my tiny little shitty room in Brooklyn," she continued. "The feeling of accomplishment filled me up. It curbed my loneliness.”

Listen to find out where Romolini is now.

The Lonely Hour is a podcast that explores the feeling of loneliness — and solitude, and other kinds of aloneness — at a time when it may become our next public health epidemic. The show is co-produced by Julia Bainbridge and The Listening Booth. Julia, the host and creator, is an editor and a James Beard Award-nominated writer.