How I'm Skirting the Rules

I’m Helping to Change What It Means to Be Powerful

Ann Shoket, former editor in chief of Seventeen magazine and author of The Big Life, is guiding the national conversation about how millennials are transforming the world of work.

Headshot of Ann Shoket, author of The Big Life

Photo credit: Anne Menke

Ann Shoket had a dream about living the big life, and she made it happen for herself largely by ignoring the typical limits others try to impose. She went from interning at Rolling Stone to working as an editorial assistant at American Lawyer to helping launch CosmoGIRL before becoming the editor in chief of Seventeen magazine, where she got an inside glimpse at millennials’ hearts and minds as they grew up. Ann describes this generation as, “the game-changing, rockstar pioneers who inspire me, and who are re-writing the rules of work, life and love for everyone.” As a leading expert on millennial women who has appeared on Good Morning America and The Oprah Winfrey Show, Ann is continuing her mission to help women tap into and wield their power with her new book The Big Life: Embrace the Mess, Work Your Side Hustle, Find a Monumental Relationship, and Become the Badass Babe You Were Meant to Be. Here the boundary breaker shares her insights on how to find your side hustle, surround yourself with a sisterhood, and create a life on your own terms.

I am Skirting the Rules by revealing how young women are changing what it means to be powerful in the world. It’s been such an inspiration to talk to this generation of young women for the book, and they are more ambitious than any generation I’ve ever seen. Their challenge is balancing the other parts of life when career and ambition are at the center. Millennials’ paths are more customized rather than linear, and it frees up us all to think about work and career and success in a whole new way. The Big Life is about the idea that young women want to make their mark, work on their own time, have freedom from the office, and find partners who get excited by the things that get them excited. There has never been a greater opportunity to succeed at work or have the relationship that you want: You can get married to your high school sweetheart or wait and have kids on your own in your late 30s. There are no longer any clear-cut rules.

That being said, I think work-life balance, this idea that you are compartmentalized into work and life, is a total sham —especially when you’re young and hungry.  The truth is, you’re thinking about work at midnight, but you’re also thinking about your life at the office at 2 p.m. I think we need employers and jobs that recognize this is the new way of working. We have to stop thinking about this idea of balance as the ideal. Young and hungry is not about being in balance—you need to stay late at the parties, get up for the breakfast meetings, and say yes to the big opportunities, while also finding love if it’s what you want.

A time when I found the possible (a creative solution) within the impossible (against incredible odds) is when I was up to be editor in chief of Seventeen at 34 years old, and almost didn’t throw my hat in the ring for the job because I wanted to focus on finding a partner. I remember feeling terrified, and had a guy friend say, “You won’t have time for dating, and a lot of guys are intimidated by ambitious women.” However, a girlfriend reminded me that, for all the dating I was doing, I still was not finding the one, so I should just take the job.

I did, and was incredibly busy the first six months. After about 10 months in, I was finding time to go out with my friends again and happened to meet this guy at a bar. We did the casual New-York-City-dating thing for six months, but it eventually got serious and he became my husband. I think I needed something of my own before I moved forward with a partner. And I knew he was the right guy for me because he got excited about my accomplishments and really cheered me on rather than felt intimidated.

The point is, you have no idea what’s coming around the corner, so keep your goals in view with how you want your life to go, and keep moving forward.

An example of how listening to my intuition has helped me is when I turned this book—which started out as my side hustle—into my main gig because it became so meaningful to me. When I left Seventeen, I knew that I had something different to say to young women and could really talk to the generation who had grown up with me about how to be the woman you want to be. But I was also doing a lot of other projects, consulting, and meetings. However, the more I focused on it, the richer it became for me. I had a series of dinners with young women to find out what keeps them up at 3 a.m., and the more I talked them, the more urgent it became. At one point I had to tell myself to stop taking on other projects, this one has the potential to affect a lot of women’s lives.

What surprised me most is that, this generation that’s so rule-breaking and game-changing, still saw age 30 as the deadline to “have it all.” Young women are anxious about having kids and relationships even as they are not afraid to succeed in business and ask for raises at work. They are still holding onto these ideas of what womanhood should be, and couldn’t make the idea of motherhood and family jive with their vision for their careers.

My secret talent is that I’m a great dancer, especially when I’m dancing to YouTube videos in my living room. I love having a mosh pit with my two kids while listening to the Ramones.

A woman is most powerful when she is surrounded by her sisterhood, and when she feels supported not only at work, but also in her personal life. One of the things I think is so amazing about this generation of young women is how supportive they are of each other. I’m seeing groups of women helping each other to become the person they want to be. In my own life, my career and my book couldn’t have happened if it weren’t for my squad of women.

I think finding a woman you want to include in your sisterhood can start with a little spark of envy, somebody who has something you wish you had, such as confidence or  passion. Then try approaching her to find out how you can be helpful to her.

 What I wish I had told myself when I was starting out is, always remember to find the fun. I had a lot of fun being in media and coming up in the world in my 20s. I went to all the parties, I launched a website when nobody was launching a site, I chased every new opportunity. I worked hard, but I wanted to go to the events and meet the celebrities. For all the ups and downs of what life is like in your 20s, that idea of bringing in the fun really sustained me.

Life isn’t always fun and you don’t jump from one high five to the next, but, if you have fun in your peripheral vision, it gets you through the challenges.

My favorite skirt (a.k.a. life hack or life rule) is, because I come from a fashion and beauty background, to get a weekly blowout on Mondays so I don’t have to spend as much time doing my hair for the rest of the week.