Overview

This story is about failure as much as it is about success. It’s a story of life’s ups and downs, its twists and turns, its ebbs and flows. This is a story about how I got rejected from college, started a band, and then found myself sitting across from the world’s top CEOs. I didn’t grow up rich, I didn’t go to an Ivy League school or get an inheritance, and either despite or because of that, I became an executive at a multinational corporation by 35 anyway.

I’m not supposed to be here. My story is about how to get lost and found and then lost all over again — again and again and again. It’s about how to find your own path and get closer and closer to naming what it is you truly desire in life while learning about yourself along the way. At many different times and under many different circumstances throughout my life, the number one question people have always asked me is, “How did you get here?” This is that story.

When I was in high school, I only cared about three things: leaving the suburbs, moving to New York City, and meeting cute boys at cool parties. I couldn’t imagine much of a life for myself beyond that. I grew up working-class poor and didn’t see any future beyond the immediate present. One afternoon during my junior year in Mr. Wilson’s history class, he was trying to teach us about World War II or something, and my best friend and I were just sitting there daydreaming about moving to New York City — imagining our cool life in the cool city with all these cool people. Our fantasy was nothing like our lives at the time. Not like the boring, dreadful old suburbs we’d been trapped in for so long. It was life of artists and excitement and adventure — what a dream that would be!

I didn’t have very many happy memories of my childhood, and so leaving the place where I grew up was the only thing that ever really motivated me. I applied to only one college, NYU Film School, assuming I would be accepted and my real life would begin. But life had other plans for me. All of my friends had already gotten their fat acceptance packages, and I ran home to check my own mail. After I saw that slim envelope, I cried and cried as I drove to my after-school babysitting job, the one I had taken specifically so I could save money for college. People kept telling me things like, “When one door closes, another one opens,” or, “Everything happens for a reason,” or, “What doesn’t kill you makes you stronger,” or insert some other variation on the same theme here. In my senior year of high school, I had just been rejected from the only college I’d applied to, my life was ostensibly over! What would I do now?! I had lost the only thing I cared about, the only thing I had ever dreamed of doing.

I eventually did make it to art school in New York City, but it happened in a really roundabout way. First, I moved to Boston and then I transferred to New York a year later. I got into fine art and politics, and explored all that the city had to offer. I spent my post-college years working on art projects, going to parties, and teaching filmmaking to underrepresented youth in the projects. I wanted to remember what it was that I loved about storytelling in the first place — something I’d always been drawn to — and give kids something they could escape to, as art had been an escape for me growing up. I didn’t have a “real job” until I was 30. I made art and traveled and curated shows and parties, and mostly made work my lifestyle.

Cut to around 2007. I had just broken up with my boyfriend of six years who I lived with and spent most of my 20s with. I had thought we’d get married and start a family, but it turned out that wasn’t in the cards for us. I was trying to figure out what to do and where to go when I had an idea I pitched to my brother, “I’m going to teach myself how to play the drums and sing, and we are going to start a band.” And my brother shook his head and replied, “Jess, you just aren’t good enough to be a musician.”

And so out of a sense of sibling rivalry and to prove I could do anything I wanted, I taught myself how to play the drums and sing, and we started to play around town. That was the birth of what would become our band, This Frontier Needs Heroes. We went on to record three albums, start a record label and travel the world playing shows. It was an amazing experience, and one of the ones I am most grateful for in my entire life. We’d be playing at big festivals in the U.K. to 5,000 people, and the other bands would be like, “Who are you? What label are you on? How did you even get here?” With some hard work and a DIY ethos, we were able to sneak in doors no one else could get into without an agent, without a manager, and without even a label.

On my 30th birthday, three years later, I found myself broke from a recent European tour with the band. So broke that I had to ask my mom for $100 so I could go out to dinner with my friends for my birthday. Everything I owned was in boxes in a basement somewhere. I had sublet my room in my apartment, and was literally sharing a bed with my best friend at the time. While we laughed at our late-night slumber parties, we also referred to that time as “the winter of our discontent.”

It was 2010 and New York City was still reeling pretty hard from the 2008 recession. I had always been a freelancer working in film, and I’d never had a hard time drumming up some new work. But this time things were different. I pleaded with a friend to get me a job, any job, and he said he could introduce me to someone at Vice, where he had been working, the next day. I went in for a quick meeting, said I thought their work was an interesting mix of politics and culture and started a few days later as a video editor on their soon-to-be-launched music channel, Noisey. I thought I would be there for two and a half weeks, and I ended up there for two and a half years. I went on to story produce and work on some of the other content channels covering art, news, and politics. I even developed my own show, and at a certain point, I just felt like I had done everything I could do there. Everyone told me not to quit, but I did anyway. After I left, I called five friends to see if they knew about any opportunities, and by way of that phone call, I got connected with a small social impact start-up called Purpose. A friend said to me, “Do you want to produce something starting tomorrow?” And I said, “Sure,” and started the next day. After a year of working there on freelance projects, I got an incredible opportunity to work on gun violence prevention and help launch former NYC Mayor Mike Bloomberg’s Everytown initiative.

Two years later, at the height of my job at Purpose, I got a phone call that my father had died unexpectedly that morning from a heart attack he had at his home. After the memorial, I laid in bed completely numb for about three weeks. My father was incarcerated for most of my life. I hadn’t seen or spoken to him in years and now he was gone forever. I couldn’t go back to New York, I couldn’t go back to work, I couldn’t do anything really. I slept and then woke up and watched TV and then went back to sleep again. When I finally got back to work, Purpose offered me a full-time position, but I decided to turn it down. I couldn’t work at the time, and while I was grateful for the offer, I knew I needed time to think and reflect.

I took six months off. I went on a solo trip to Hawaii because I had always wanted to go there, and I knew that Joan Didion had done a lot of her writing there. I went to a meditation retreat, and drove around staring out the window. I listened to songs on repeat for hours. I didn’t talk to another human being except for this amazing Japanese woman who told me to leave New York and never look back. I almost moved to L.A. I thought New York was over for me — that it was time to say goodbye to all that. I slept at my friend Olivia’s bungalow in L.A. for what felt like a million weeks. I was so depressed, I didn’t want to do anything. Half a year later, I eventually came back to New York but after a year, I got laid off during a company reorganization. I had never been laid off before, and I was hurt that after all of my dedication and hard work I would actually lose my job instead of being rewarded for it. While it was difficult at the time, I later realized that I was learning something valuable — that layoffs are a normal part of modern work life and what is now an ever-evolving landscape of constantly merging industries. You can be prepared for them and accept them as a part of life, or you can let them take you by surprise and spiral. I learned then to always be interviewing, always be meeting people, and always be learning about new opportunities. Never rest on your laurels.

One month later, I got a phone call from a friend that would change my life forever. RYOT, a social impact media startup who had evolved into a Virtual Reality documentary production company, had recently been acquired by what was at the time Huffington Post, and they needed someone to come in and start the NY office. I would have to become a virtual reality expert overnight and would be traveling around the world talking about the future of media.

My first day on the job was the day of the Orlando Pulse nightclub shooting, and I had to learn on the fly how to make a piece of breaking news coverage around a traumatic event in a Virtual Reality format I had never used before. Then I had to make it go viral. Somehow we figured it out. From there, and in a short amount of time, I went on to build the global creative agency, with 16 offices around the world, for all of what was to become Verizon Media.

Given my non-traditional career path, people often ask me to give a talk on the secret to my success. At a recent Verizon Women in Tech conference, the first question I got asked after my keynote was, “Have you ever thought about writing a book? Your story is so inspiring.” And that’s what brings us to this. People have always told me they’re inspired by my accomplishments. Once while I was on tour with the band, a couple in New Mexico offered to make my brother and I tacos if we talked to their kids about how to follow their dreams. Friends have even admitted that they’ll often ask themselves, “What Would Jessica Do” when contemplating big life decisions they need to make. On Halloween last year, I ran into a girl I used to work with who was very drunk and stopped to tell me she followed me online and was so inspired by everything I’d accomplished. And just last week, a friend wrote to tell me how grateful she was to have me in her life as a mentor and career coach. This is my humble attempt to make sense of all that.

I’ve had a million lives, a million setbacks, a million horrible, traumatic things happen to me throughout my life. But somehow I’ve continued to amaze even myself with what I’ve been able to accomplish. I read somewhere recently that life is not about finding yourself, but creating yourself. Perhaps a life well-lived is the most creative thing one can ever do. My mother always taught me that I could be anyone I wanted to be, and that I could do anything I dreamed of. I believed her. She grew up on a farm in South Carolina and dedicated her life to letting me dream of being whoever I wanted to be. This is for her.

This book is not about me — it’s about you. I don’t have any of the traditional pillars of success — I’m not married, I don’t have kids and I don’t own a home— and I’ve had an amazing life anyway. Some people will say that I don’t know what I’m talking about, or that I’m a white kid from Connecticut who has been able to use my privilege to my advantage or that I’m not all that successful anyway. They might wonder, “Who is she to know anything about anything?”All of which is true, and not true at the same time. More than anything, I believe that our lives — all lives — are worth sharing. And worth documenting. And that talking about the human experience is pretty much the only thing worth spending your time on.

In the end, I will tell you this — I’m just like you. I’m just an ordinary person who started off with no help from anyone, no money in my bank account and with no industry connections who set out to lead an extraordinary life. I’ll share with you everything I thought I knew then, and everything I know now; everything I learned, by trial and error, by figuring it out myself, without anyone pointing out the way. There are some secrets you can learn, like how to build your network, how to transition across industries, how to exude confidence and play a room, how to use fear from within to cultivate power, how to stop thinking so linearly and transactionally, how to steal from the best, how to hack the system, how to learn to work like a man and how to unlearn working class narratives. Mostly, though, it’s about following your heart, believing in yourself and having the courage to fail — before you succeed. Because when you follow your heart, the rest just falls into place. I hope this book inspires you to live your dreams, whatever those may be, or wherever they may take you.

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