We all are in need of mentors; women and men who have gone before, seen the patterns endemic within our spheres and come out with wisdom and (hopefully) a little extra kindness for those just arriving to the scene.

Ann Shoket is emerging more and more as one of “those voices” that we here at Darling want to be attentive to. Her book, “The Big Life,” has just hit shelves and she is immersed in her goal of creating a network of women who are ambitious, heartfelt and honest — three qualities the woman herself has long embodied.

From crafting her own online blog as a “side hustle” to sitting as Editor-In-Chief of Seventeen magazine for almost eight years, Shoket has seen (and heard) much. It’s hard to find mentors that tick so many boxes: feminist, empathetic, kind, smart, articulate and actually fun to be around. We hope you learn from and enjoy the thoughts of Shoket as much as we do.

Teresa Miller Archer: So tell us a little about what prompted you to write “The Big Life.” What’s the story behind it?

Ann Shoket: When I became Editor-in-Chief of Seventeen in 2007, it was the year of Lauren Conrad. Everybody wanted to be blonde and drive their car through Southern California with the windows down and just assumed they would be successful. It was the rise of the Kardashian era. Then the terrible recession of 2009-2010 came, and yet, rather than feel like their world was getting smaller, this generation of young women got laser-focused on career and ambition and success … and I could see it from where I was sitting. In a year, I got called maybe a dozen times to give speeches about how to get started in your career. Women were sending me non-stop messages of, “How do I get started? What do I need to major in in college?”

I said, “I know, I’m gonna invite some women over for pizza and wine and talk about relationships and sex.” I had six or eight women around my dining room table. I heated up fancy frozen pizza. I made a killer cheese plate and I opened up a lot of wine. We talked about relationships and sex for about five minutes. The rest of the conversation was about co-workers and toxic bosses, the phenomenal pressure to be perfect, to be “on” all the time, to be Instagramming. It was the most amazing conversation I’d ever had.

I’d been editor-in-chief of a major magazine for eight years and to have these women around my dining room table, women who grew up with me, and to hear the complexity of their challenges, the depth of emotion they felt and the hunger they had to make their mark on the world was eye-opening and life-changing. I knew I had to do that dinner again and so I did … and again and again and again and over the course of two years, I did two-dozen or more dinners.

That conversation is what became my new life. When I say I wanted to continue the conversation I had with this generation of young women, I mean it. It’s a conversation.


TMA: Can you describe what you mean in the book when you discuss having a “side hustle” and what women might gain from pursuing one?

AS: Whatever your job is not providing you, that’s what your side hustle should be. If you are not in a position in charge and you really want to be in charge, get a side hustle that puts you in charge. If you have a job that’s not giving you great meaning, get a side hustle that gives you deeper meaning.

Your job is what you do to pay your bills and the side hustle pays you in self-respect because — especially when you are young, hungry and ambitious and you have so many ways to make your mark you feel confused about where to go and what to do — the side hustle is a way for you to explore all of those opportunities and possibilities. And to see, to try it on for size, right?

I had a side hustle. I launched a website when I was coming up. It sounds like, “Oh yeah, everybody has a website now.” [This] was 1996: Nobody had a website. But it gave me entrée into meetings at my job job that everybody was like, “Who understands that Internet thing? Go get Ann! She understands.”

Suddenly, I was an expert in a realm that my bosses didn’t understand. By day I was an assistant, but by night I was editor-in-chief, and it gave me a greater sense of my possibility. I knew it was time to end the side hustle when my job was really engaging and demanding. But there’s a woman in the book who used to work for me who had a side hustle and she stopped working for me at Seventeen because her side hustle got more demanding and engaging. And that’s when she knew it was time to leave.

If you have a job that’s not giving you great meaning, get a side hustle that gives you deeper meaning.

TMA: What tendency or habit do women seem to have today that you think is extremely helpful for them finding what they want and which do you think could possibly hinder us if left unedited?

AS: Well, I think it’s both the same habit. I think this desire to move up and move around and cover a lot of ground and make your mark is an amazing quality of this generation, right? This hunger, this confidence that you can figure it out, that you will make it happen, you very quickly go from, “I don’t know anything … I can’t believe they hired me!” to like, “I know everything. This job is a breeze and I’m ready to move on and move up … I’m gonna go ask for a raise.” And that — probably like a nine-month learning curve — is the friction between this generation and their bosses.

Because you walk into your bosses’ office after nine months and you say, “I’m ready to move up. I’m ready to move around. Please promote me. Give me a title change and a raise.” Your boss is looking at your nine-months as a blip in her [own] career and it’s not in the budget, it’s not in the strategic plan and she doesn’t frankly have a corporate structure set up to give you a task force, to give you a think tank, to give you some project to work on, right?

It’s in that moment of friction where you say, “Ok, what do I have to do to get to the next level? Can you give me any other projects that will satisfy this itch that I have? And when? When can we revisit this conversation?” Then sit still until that ‘when’ happens. Get another six months, get another nine months, whatever it is. Pin her down. Because I don’t think you should sit still forever. I think that companies that are not moving you up, moving you around, giving you task forces, giving you reach projects, are going to lose you. And that‘s okay. You will find the place that you need to be.

TMA: If you could put a spotlight on a woman, known or unknown, who is making a dramatic change and she’s highly influenced you — who would that be?

AS: You know, I talk a lot about the squad I need to build and there’s a woman who wrote a book and her journey paralleled mine and we were introduced sort of early on in our book-writing process. She could have very easily felt competitive with me and not wanted to be collaborators. Instead, we went through the journey together. [We] traded notes and sent each other emails and emails, “Hey, did this weird thing happen to you too?” Or, “I’m having this weird scenario, can I ask for your opinion?”

Her name is Tiffany DuFu and her book is called “Drop the Ball.” I am so rewarded by her friendship and her support. Her book is aimed at sort of the next phase of women. It’s about when you have children and how that changes your life. It’s been such a rewarding friendship and partnership, and it’s also been so comforting to have somebody who’s going through all these complicated things alongside me.

Check out Ann Shoket’s book, “The Big Life” on stands now and online.

Images via Anne Menke



  1. Loved this!!! I’m definitely going to have to check out this book. Game changer: your side hustle can meet your passion and hunger when your day job isn’t! It’s about figuring out what works for you, not being content with “roadblocks.”

  2. LOVED this inspiring article. It was just what I needed to hear! It’s so easy to get discouraged when you’re fresh out of college and looking for a career path. I love the idea that she mentioned of the side hustle fueling our self-respect and ambition for life. Definitely going to pick up a copy of her book, too!

    1. Hi Victoria! YES, I actually am circulating the book around my interns in the Darling office, because it has so many great touch points for work ethic, self-respect, and planning your “work life.”

  3. I devoured this book in less than 24 hours. I felt like finally someone had put words to how I felt about my career (and realized most of my friends thought very differently). I also really appreciated that she covers a wide range of careers and not *just* creative/entrepreneurial ones – which I just can’t relate to.

    1. I so agree Jessie, there was a great variety of perspective in this book, very unusual for the “work woman”/girlboss books out there right now.

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