Ann Shoket has always connected in a very real way to a generation of young women, from helping to launch CosmoGirl to becoming the youngest editor-in-chief of Seventeen. Now, she’s published a book for women growing into adulthood and searching for “The Big Life.”
Do you remember your first week in New York?
I moved from the suburbs of Philadelphia to go to NYU, just after I turned 18. I was looking at a few difference schools in the Northeast, but when I came to New York, I instantly knew this was where I wanted to be. I remember sitting down in Washington Square Park, just watching people go by and feeling so excited by the energy. I knew that this was where I had the greatest possibility to become the woman that I wanted to be. This was in 1990, so Washington Square Park was a little more edgy at that time. I still thought it was fantastic.
So when you actually moved here, did you feel like you’d made the right decision?
I was instantly overwhelmed! There was so much to do. I was living alone for the first time. NYU is actually a bit of a soft landing, if you're coming to New York for the first time. They really do a good job of making sure that you get some structure and feel connected to the community and you're not just left to your own devices. Of course, during the times when you are left to your own devices, there is a lot of trouble to get into! I just loved it, all the different people you could meet every day. I thought everybody had an amazing, fantastic, fun story and it was an exciting time to be in New York. Although, during that time in the early ‘90s there was a terrible recession. So when I graduated, I was of the mindset to get a job, any job.
What did you study at NYU?
I did a BA in English Literature and Creative Writing, with a Minor in Political Science and Latin.
And what was that first job you managed to get?
I got a job at The American Lawyer magazine. It sounds like a super boring job, but at the time I had applied everywhere and this was the job I could get. I had been to so many interviews, and the woman who interviewed me at The American Lawyer was looking for a replacement for herself. I saw a spark in her eye, and I said to myself, “I'm not going to stop talking until I’m convinced this woman is going to hire me.” And so I did—and she did. It turns out that The American Lawyer was actually a fantastic place to have a first journalism job. I didn't know that at that time, but I was tremendously lucky.
It was run by this legendary journalist, and the company was filled with very smart, dedicated and experienced reporters. It taught me how to be a very good journalist. I started out as a fact-checker, which was a bit boring but it taught me the rigors of journalism, the underpinnings, and how important it is to get it right—even down to the commas and the ampersands. It taught me how to write precisely. We’re in such a different stage of journalism now, I feel a lot of that gets lost. It was such a brilliant education for me. And, during my time there, the other cool surprise was that the OJ Simpson trial happened!
Wow, that’s perfect timing to work at a legal publication.
We were positioned at the right place at the right time. The company that owned the magazine also owned CourtTV, and this was really the first big moment for multi-platform journalism. It was an exciting time to be there. Who knew that my snoozy fact-checking job would turn into something that was at the center of a big cultural conversation?
It seems that throughout your career you’ve been on the cusp of the next big thing.
I'm driven by boredom. My entire career is driven by this fear of being bored. I don't want to sit in my office and do things the way they have always been done. I don't want to do the job the way the woman before me did it, or the woman before her. I want to tread into new territory and figure it out. I want to pay attention to where the world is going. I want to be a part of the change that's happening in the world. That feeling was awakened during that first job.
So when I went to work at the launch of CosmoGirl, it was during another big time of change for publishing. It was New York City in the ‘90s, so either you were launching a dot-com or you were going to work at a startup. Everybody was looking over their shoulders at San Francisco. At the beginning of CosmoGirl, we were basically four girls in a room over an overheated copy machine putting out a magazine. But we were on a mission, and that's what made it worth it. I often spent the night sleeping under my desk. It was rigorous! At the same time, we were still a startup for a giant company, so we did have a nice safety net.
Did that safety net allow you to push the envelope a bit more?
Maybe. But the main thing was that I knew my checks were going to get cashed, you know? I was supporting myself and I needed to get paid. I knew a lot of people who worked at startups and wouldn’t get paid. I wanted to make sure we continued to do it right. Every dot-com and tech company was launching something new and big and exciting, and there were a million huge, extravagant launch parties. After a while, though, it was like, "The bigger the party, the faster the fall."
I went to this one fabulous party at some warehouse space along the West Side Highway. It was packed with everybody who was anybody, but I couldn't find a single person who was there to talk about what the product was. Two weeks later, they announced the fall of that company. It taught me a really important lesson about putting my head towards the business, and being humble and respectful, and spending money in a smart way.
I was at CosmoGirl for seven years. I loved that magazine; I was part of the team that grew it from the ground up. I ran the website, created the digital platform, and came up with special projects. So when the job of editor-in-chief of Seventeen magazine opened up, I knew that it would be an amazing next step for me. But I wasn’t the first one in line for that job! In fact, I know that they interviewed maybe 40 other people before me.
That must’ve been a lot of pressure!
It was a huge step to take and naturally, it made me question my ability to achieve in that role and space. I think it's human nature to say, "Why me? Can I do this?" But I knew that I had a good idea, and I knew that I understood that generation of women. I knew how to talk to them about the things that mattered, because those things mattered to me, too.
I ultimately knew it was the right time for me to make the pitch and to step into that role. It was a really big deal. I'm often asked questions by young women who are thrown into management positions for the first time. They’re understandably nervous, just like I was. There are so many questions: How do I manage people who are my age, who’ve been my peers? How do I manage people who are older than me?
My advice is to be real and authentic and not suddenly step into some artificial role of what it means to be a boss. Be clear about your vision and about what you expect from other people. And don't change your mind! I think it's okay to say, "I don't know exactly what I want to see here, but let's work it out together." But it's really unnerving to your team if you say, "I want X." And they deliver X and then you say, "I don’t know, I think I want Y." It's the fastest way to lose the respect and loyalty of your team. I think it’s a muscle you have to learn how to flex, which is to be confident in your decision-making and how you communicate a message to your team.
What was the biggest change for you moving into that role?
It was a big shift to go from being number two at a magazine, where it was my job to execute my boss' vision, to being the person who had the vision and to figure how was I going to get a team around me to execute it.
During your time at Seventeen, there was another recession. How did you navigate that change when speaking to young readers?
When I first arrived at Seventeen, it was 2007. It was the year of Lauren Conrad—everybody wanted to be blonde, tanned, and drive their Mercedes SUVs through Southern California with the wind blowing in their hair. It was a year of conspicuous affluence.
Such a different time, but I remember it so well!
Fast-forward two years, and we’re in a terrible recession. The future that these young women had been promised suddenly felt really far away. But rather than let the rug be pulled out from underneath them, this was a generation of young women who took control of their destiny. I could see it from where I was sitting at Seventeen. I started to get tons of emails and messages saying, “What do I need to do now in high school? What do I need to do in college? How am I going to get started now?” Before this moment, success was assumed. Now, they were getting mobilized to make that success a reality. We pivoted the magazine around this idea. We launched a money column, we talked about girl power and how to think about success. This is a generation that couldn’t care less about having it all. They want to create success on their own terms.
Yes, these are Millennials. They grew up with me at Seventeen, and I also grew up with them in a way. Now, they are in their 20s and 30s and they don't want to sit still and wait to be promoted. They feel confident in their ability to get off the beaten path and to craft a job that works for them. They want freedom from the office, freedom from the old rules. The status symbol now isn’t shoes or bags, it’s a MacBook Air, because it means you are free to work anywhere, and on your own terms.
Watching this change led me to write The Big Life. I’d spent all this time fanning the first flames of these young women’s goals and dreams. I never understood why those conversations should stop, just because they grew into their 20s and their subscriptions to Seventeen ran out.
Do you stop talking about all of the complicated emotions around wanting something so big so badly? The stakes are higher when you're in your 20s. The decisions that you're making matter more. You're moving towards becoming the person that you want to be.
It’s interesting, though, because even though I’d been writing for Seventeen for so long, and talking to Millennials for years, I realized there were some things I didn’t know. We didn’t talk about sex and relationships at Seventeen, so I didn’t know much about that. I asked a group of women over for dinner, and thought I could pick their brains and then I would be able to write the book! This dinner was amazing—six women, frozen pizza, plenty of wine and some truly insightful conversation.
After that first dinner, I felt like my brain was on fire. I went downstairs and said to my husband, "Oh my God, I have to do this again!" And so, I did. Over the course of two years of writing the book, I had dozens of dinners at my kitchen table. Same formula: six or eight women around my table, fancy frozen pizza, many bottles of rosé, killer cheese plate.
The dinners became so meaningful to me. The conversation was richer and stronger and more powerful than I had ever imagined it could be. Many of the women who sat around my table became sort of “characters” in the book. It was a big shift for me in writing the book—the advice in the book became “me too” instead of “how to.” It was about creating a sisterhood of women who are sharing their stories to help other women achieve and succeed. I think there's someone in the book for everyone. I called the dinners "The Badass Babes Dinners," because those women are badass babes, right? They're the kind of women that you want in your orbit. They are strong, competent, and dynamic, and rich. Everybody needs to have their sisterhood around them.
The Big Life is not a book about Millennial women. It's a book for them. It's about their experiences and I'm experiencing those things, too. I have lived my life as Millennial as possible. I get my media online, I communicate to my audience through social media and I work at a coworking space. I love being free from the office and the traditional rules. The things I have learned from the women around my table are the things that I am trying to put to practice in my life. I am embracing the adventure of this new path, this new dynamic that Millennial women have set up for how a career can go. I don't know what's next, but I am loving every minute of it.
What’s the biggest lesson you've learned from Millennial women?
Their ability to replace competition with collaboration. There is this old, dusty idea that there was room at the table for one woman and you had to wait until that woman, like, fell over and died before you could get a seat. It's just not true anymore, because there's more room at the table for more women. And, because there is more room, women are helping each other get other seats at the table. Obviously, we still have a long way to go, but we’re getting there. Sisterhood is the key to success for everyone, and it's being driven by Millennial women.
What does New York mean to you?
I still have the same feeling of possibility in New York as I did when I first arrived. I don’t ever want to be in a place where I'm not looking ahead to what's next. New York is definitely a city that is conducive to that. It has given me so much. In fact, when my husband and I first started getting serious with each other, we basically shook hands and both agreed that neither of us would make the other move out of the city. [Laughs]
Order a copy of The Big Life here.