Ann Shoket with Jessica
Culture Life

Takeaways from an Evening with Ann Shoket

You may not know her name, but you definitely know her work.

Ann Shoket was Editor-in-Chief of Seventeen magazine from 2007 to 2014, and is at least partially responsible for you being the young woman you are today. I mean, where else would you have found tips for getting a cute butt without exercise AND getting into college?

Her latest achievement is becoming the author of “The Big Life: Embrace the Mess, Work Your Side Hustle, Find a Monumental Relationship, and Become the Badass Babe You Were Meant to Be”. (I dare you to say that five times fast!)

Ann Shoket Book Covers

And that’s what led me to meeting her at an informal discussion of her latest work at a funky bookstore with lots of personality in Coral Gables called Books and Books. There were close to 30 women of all shapes and ages ready to learn from Ann how to embrace their mess, work their side hustle, and everything else the book and signage advertised.

These are their stories. BOM BOM. (I’m kidding.)

But here are my takeaways from an evening with Ann Shoket!

Ann Shoket, Alicia Menendez

Had to snap a pic with Ann Shoket and the talk’s moderator (and my colleague) Alicia Menendez!

“That feeling of possibility goes away.”

Not exactly the feel-good sentiments I expected, but it grabbed my attention.

Ann began her discussion by breaking down the very real truth about what getting older feels like (“what am I doing with my life?” sprinkled with the occasional “this isn’t what I want to do with my life!”) and how the “shoulds” of life are actually causing us to chase after an ideal that doesn’t necessarily exist anymore.

Want proof? Just listen to this mother/daughter pair discuss both of their lives at age 27. LOL at being married for five years.


So what did Ann Shoket do? Naturally, she wrote a book—her impetus being that this generation is so different from previous ones (“Your possibilities are more!”) and as such, there aren’t many established paths for what love and success look like for us.

“Work-life balance is bullshit!”

Many of Ann’s quotes are the human equivalent of the clapping between every word emoji and make for great Instagram captions.

Her explanation for why the common phrase is BS is because life and work are put in competition with one another so much so that we can’t even come up with another turn of phrase to encompass a life that is truly balanced. And if women’s representation in media is an indicator of anything, let’s talk about how women always get the short end of the work-life balance stick. Work all day to work at home during the “double shift” with cooking, cleaning, child rearing, etc. right?

“It’s a privilege if your work feels like your life.”

As a result, millennials have perfected the art of the side hustle. Because let’s face it, how many of us are doing exactly what we want, feeling fulfilled, and being paid for it?

But Ann made sure to differentiate between earning extra income (driving for Uber, baby sitting, etc.) and being strategic with a side hustle in order to get more.

According to her, a side hustle provides someone with the things she’s not getting from her work. Think you’re not being challenged enough? Put yourself in charge of something. Feel like your occupation isn’t providing you with meaning? Give yourself a purpose.

As lovely as this sounds, is there a time when your side hustle can become your actual hustle?

“When it becomes more vivid for you.”

Ann Shoket, The Big Life

Do your due diligence

One thing I appreciated about Ann’s discussion was that she didn’t pretend that things will work themselves out on their own and she didn’t encourage everyone to quit their day jobs in order to achieve their version of millennial success.

“Before you go for it [and] if it’s too terrifying, it might not be the best moment to just jump.”

But that’s not to say she had answers to everything. During the Q&A session, I asked Ann about whether her book was intersectional and relatable to women of color/working class women and, unfortunately, her initial response was less than stellar.

“I want to make The Big Life for everyone, not just the girls who were the ‘It’ girls or the ones who always raised their hands in class.”

I was disappointed but didn’t press the issue.

Ann Shoket

Final thoughts

Later on, Ann and I had another moment to speak as she signed copies of her book. I approached where she was seated and she joked about the degree of difficulty of my question before her tone turned serious as she clarified her words.

“I want this book to be for everyone, not just women who look like me. Everyone is into the notion of being the boss of their lives.”

Based on the night’s discussions, casually stalking the web for reviews, and thinking about my future, I do plan on reading her book.

Nothing is perfect and I want to give The Big Life a shot. But most importantly, one of Ann’s quotes has particularly resonated with me.

“You have one life and it has to be big. And it has to be the way you want it to be.”

She’s right. And I’m working on it.