Dot Complicated: Untangling Our Wired Lives (2 page)

I dumped my work bag on the ground heavily. I felt a sudden kick from the baby.

“Great job today,” he continued. “Really huge props. It was awesome and everyone’s talking about it. I can’t believe you did it in two weeks.”

That’s when it happened.

“Mark . . .” I began slowly. “This was the best day I’ve ever had at Facebook.” I paused for a moment, trying to work out what to say next. And then I was off on a roll.

I blurted out to him that this was what I loved doing. This was how I saw the future of live programming—reaching millions of people with amazing content produced for the web, produced for another generation. That all those days and nights working for this moment had shown me what my true passion was, and that it was something that went beyond my role at Facebook, or even Facebook itself. The entire media landscape was changing—how we got our news, how we experienced live events—and I had to be part of it. I needed to pursue my passion, all the way.

Words tumbled out of my mouth, too fast and unprepared.

“I want to leave.”

The words hung in the air. I stopped, suddenly self-conscious and horrified with myself. I had never said any of these things aloud. I didn’t even know I truly felt this way until I had spoken the words. I stood there in my entrance hall half wishing I could put the words back in my mouth.

Mark stared at me. Beast stared at me. I resisted the urge to giggle. Beast is too shaggy and adorable to be part of any serious conversation.

If Mark was fazed, it didn’t last for more than a heartbeat.

“Are you sure?” he asked calmly, as if he had been expecting it.

I hesitated for a moment. I thought about all the people, all the moments during these past five and a half years on the crazy roller-coaster ride that was Facebook. For a moment, my mind raced through a hundred different memories and emotions.

There was a reason I had said the words I never thought I would say and why I felt so restless. These ideas and feelings had been brewing in me for a long time.

I was going to miss Facebook, but I wasn’t afraid to leave. It wasn’t the first time I had taken a chance to follow a different path.

The Beginning of the Adventure

I was born in 1982 in Dobbs Ferry, New York. I grew up in a perfectly normal (well, sort of) upper-middle-class family. I am the oldest of four siblings; after me came Mark, Donna, and Arielle, the youngest. Both my parents were doctors: my mom, Karen, a psychiatrist, who had Mark and me while still in medical school and somehow managed the crazy overnight hours of residency while also raising two screaming toddlers, and my dad, Edward, a dentist, whose office was located on the ground floor of our house (how’s that for a commute?).

Our town was a quiet suburb about forty minutes north of Manhattan, consisting of 1970s split-level houses laid out along quiet, tree-lined streets, on which minivans carrying soccer-uniformed children drove by. It doesn’t get much more typically suburban than Dobbs Ferry, New York.

For most of my childhood and teenage years, right up until college, I led a wonderfully normal life. In the winter, we went skiing. In the summer, my parents shipped the four of us off to summer camp. I begged my parents to take us to “splinter park,” a park made entirely of wood, even though every visit consistently resulted in hours of painful tweezer removals. I brought home the chicken pox, and I graciously shared it with the entire family—even Arielle, who was only six months old at the time. And I attended the local Ardsley public schools, dutifully singing the Concord Road theme song every morning, until I switched to Horace Mann School later on.

I guess you could say that I was always a bit of a go-getter. I took piano lessons and somehow negotiated to spend the majority of my lessons singing, while my teacher played the piano. I ran cross-country and had my parents drive our car alongside me on the street so I could feel the pace I needed to run to make the varsity team. I acted and sang in school plays, community plays, summer camp plays—in any show that would have me, really. In high school, I expanded my interests. I became really passionate about studying and singing opera, and I joined the varsity fencing team, where I eventually became captain. I studied really hard in school, got good grades, and in 1999, despite having no special connections or advantages, became the very first member of our family to attend an Ivy League college, when I was accepted to Harvard University. To this day, I remain the only member of our family who has actually graduated.

People always ask me, “How was it growing up with your brother? Could you tell he was going to start a huge company back then?” The answer is a plain and simple no. We were a totally normal, happy family. Besides, don’t count the rest of us out yet. I have a feeling we’ll all be working for my youngest sister one day.

Fast-forward to April 2003. I had spent the majority of my time at Harvard studying psychology and singing with my beloved a cappella group, the Harvard Opportunes—and now my time at Harvard was ending.

My friends and classmates showed how it should have been done. In those final frenzied weeks after spring recess, every lunch, every party, every dash through Harvard Square was filled with happy, excited people—people with plans,
lots
of plans. And all those lofty ambitions and epic next steps could be summed up with names: McKinsey, Goldman Sachs, JPMorgan, Deloitte. It seemed everyone was heading to Wall Street or K Street to work in banking or consulting. Conversations with friends had become little more than summaries of future résumés.

At some point, the conversation would turn to me. “So, where are you heading, Randi?”

I would smile and look apologetic. “I haven’t quite decided yet. I’m thinking of something in the creative industry.”

Often these words produced only blank stares. Most of the on-campus recruiting at the time was done by consulting and investment-banking firms, so perhaps it hadn’t occurred to my classmates that other types of work existed and that one might even find those other types of work rewarding. (The shock!)

In any case, I wasn’t deterred. I had no interest in quantitative analysis or statistics, and the idea of gazing at spreadsheets all day bored me.

Several weeks before graduation, I began hunting for openings at advertising and marketing companies in New York. At one point, my dad excitedly told me that one of his patients worked for J. Walter Thompson advertising agency and was going to recommend me for an interview. It was really sweet; my parents, both doctors, clearly wanted to help me with my desired career path, but they had no direct connections whatsoever to marketing or advertising. Still, they were eager and excited to be able to help in any way possible.

A few weeks later, I walked into J. Walter Thompson and greeted my interviewer with a firm handshake and the necessary amount of confident yet friendly eye contact.

My interviewer beamed at me. “You’ve come
highly
recommended,” he said.

I beamed back. And I was just starting to feel assured of success when I read upside down the Post-it note attached to my résumé lying on the table. “Dentist’s kid. Courtesy interview. Thanks!”

I didn’t get the job.

Several unanswered résumés later, I landed an interview for the data and statistics team at Ogilvy & Mather, a Manhattan advertising firm. Yes, I know what I just said about statistics. But I did love acting, and I figured maybe I could carry off a convincing impression of an undiscovered prodigy in mathematics.

Needless to say, I completely bombed the interview.

Questioning complete, I began gathering myself to leave. As I headed for the door, a friendly looking man appeared in the doorway. It was the hiring manager for the entry-level program.

“Well, Randi,” he said. “Clearly your passion isn’t statistics.”

I decided to abandon my Oscar-worthy performance and murmured my agreement.

“But,” he continued, “you seem creative. A position recently opened up in the client and creative side. Let me just make a few phone calls.” A few more interviews, and a few days later, it was official. I had a job.

I had envisioned myself taking a few weeks off between graduating and starting a job, but when Ogilvy called, asking if I could start immediately, I didn’t argue. The Monday after graduation, I started working.

At first, I lived at home and commuted to work on the train. It was surprisingly fun and nice being back with my parents and my youngest sister, who was still in high school. But the long commute quickly started to wear on me. Besides, I was eager to start my new life in the city. After a few months of saving up as much money as I could, I decided it was time to move to Manhattan. I was ready for a new and glamorous adventure.

At Ogilvy, I was placed on a fairly new team called “interactive and digital media.” Of course, I had imagined myself in the far more exciting surroundings of TV sets and magazine photo shoots. Later, in retrospect, it turned out to be a hugely fortuitous placement. As the power of the Internet grew, my team and my responsibilities grew exponentially, while my friends who had been staffed in the more glamorous jobs were still going on coffee runs. But at the time, I didn’t realize how lucky I was.

It was also clear that this was not the creative role I had hoped for. The days were long and mostly spent photocopying, binder filling, three-hole punching, staple removing, and spell-checking memos drafted in legalese.

Even worse, I had a mean boss. She consistently referred to me as “her project” and would do bafflingly cruel things. Once she invited me to give a big presentation to the department head at 2:30
P.M.
the following day. I was so excited. Now was my chance to shine! I stayed up late that night practicing my presentation. The next day, she showed up at my desk ten minutes before the meeting.

“Randi, where have you been? The meeting started twenty minutes ago!”

She had moved the meeting and told everyone except me, giving her a chance to reprimand me for being late and irresponsible in front of the department head and bolster her tough-as-nails image. It was the most humiliating experience of my life. (Tip: If you hide in a restroom stall, you can muffle a quiet cry with a courtesy flush and no one’s the wiser.)

But I do have her to thank for my Naked Cowboys.

The Naked Cowboys was a tight-knit group of entry-level staffers to which I belonged. We had adopted the cowboy moniker as an homage to the strange, long-haired guitar player who wandered around Times Square every day wearing nothing but a pair of white briefs and cowboy boots. He made a living posing for photos with tourists and raked in a ton of money. He was obviously a secret genius marketer, and he inspired all the shadeball Elmos and nightmare SpongeBobs that haunt Times Square today. It seemed fitting to honor him.

The purpose of the Naked Cowboys was to take on an actual marketing campaign for a nonprofit, above and beyond our daily duties. It was part of a prestigious career-development program within Ogilvy for new(ish) hires, which my boss had recommended me for. It was a win-win for everyone. The nonprofit got a free ad campaign, we got invaluable experience, and Ogilvy got us to work late every single evening for three months, as we were required to work on these campaigns on our “own time.” It was grueling finishing a full day of work and then starting another session that lasted until ten or eleven each evening. After we were assigned an ad campaign for the Special Olympics, we worked even later, usually past one in the morning. But the work was fascinating, and I enjoyed being part of a crew. All those late nights and intense sessions together inevitably made us the best of friends.

There were also my other friends. I had taken to life in the city like a duck to water. I took the Craigslist gamble and found a room in a Hell’s Kitchen “converted” four-bedroom apartment, which meant I was living in a portion of the living room fenced off by a sheet. So, the apartment was a little sketch. But I loved my roommates, and they became part of my crew. I now had enough people to have fun with. And, boy, did we have fun.

During that time, in the courtyard outside Ogilvy & Mather, I shared a bunch of margaritas with a wonderful guy (and Harvard classmate) on an amazing first date. I didn’t know it yet, but he was the man I would end up marrying: Brent Tworetzky.

It was 2003, and I was twenty-two years old. The city was hot and vibrant. I was living paycheck to paycheck with no savings to speak of. But I was young, surrounded by friends, and making my own way in New York. I was happy.

Against this backdrop, I was dimly aware that Mark had started working on a new project: Facebook. Or as it was known back then, The Facebook. The site had gone gangbusters at Harvard and had started to spread to several other U.S. colleges.

Occasionally, I would ask my colleagues whether they had heard about The Facebook. Everyone my age was familiar with it, but no one over twenty-four seemed to have a clue.

Still, Mark was clearly on a roll with the site. He had just flown out to California to secure funding for his company. He asked me if I wanted to come work with him.

Despite my misgivings about corporate life, I politely declined. I hadn’t given up on New York just yet. But as time passed, I continued pondering my future plans.

So, that was my life as a New Yorker. I assumed the experience was uniquely mine, that all the joys, ambitions, worries, and dilemmas were special to me. But of course they weren’t. All these things would be instantly familiar to young professionals who have ever dared to strike out on their own in the big city. The experience of being a newcomer in New York, despite growing up so close to the city, is one shared by tens of thousands of new grads, interns, and struggling-artists-cum-hipsters every year. I lived a life that was no different, no more exceptional. But that’s the thing about New York. The unexceptional thing about most new arrivals is that they all want to be exceptional—and that was certainly true for me.

I didn’t have a lot of money or connections. I didn’t have the dream job, the dream apartment, or the dream career mapped out. But I still had a dream, as vague and ill-formed as it was.