Ann Shoket is the former Editor-in-Chief of 17 Magazine and the author the Big Life. Having seen the millennial generation grow up first hand, she knows what it takes to rock it as a millennial woman.


Ann Shoket is the former Editor-in-Chief of 17 Magazine and the author the Big Life. Having seen the millennial generation grow up first hand, she knows what it takes to rock it as a millennial woman. Click here to check out our interview.


In this episode, you can expect to hear….

What makes millennial women unique 👯🏾‍♀️
Why a side hustle is THE MOST important part of The Big Life 📲
What my own side hustle does for my life 👜
The true purpose of a side hustle (*chills*) 🌟
How a personal brand exposed what unites us all 👭
What keeps you going when working for yourself 💌
Ann’s biggest takeaway for millennial women 🎁

Join Ann’s tribe of women here:

Podcast Recording

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The replay of FB Live Interview


Transcript of Interview with Ann Shoket

Leah Gervais: Hello everyone. Happy Friday. Thank you all so much for tuning in. Those of you that are here live, and those of you that watch the replay, I would love to hear where you are tuning in from. My name is Leah Gervais, I am the founder and the creator of, and I am interviewing one of my biggest role models in the world, Ann Shoket. So, this is a very exciting time. We’re very lucky to have her here. So, we are going to get right into the advice she has for us. But I’m going to give her a bit of an introduction first. So thank you so much for being here, Ann.


Ann Shoket: I’m excited.


Leah Gervais: Good. Great. Okay. So for those of you that might not know, Ann has been at the front lines of a revolution in the media industry and in the lives of young women. I have heard her put it that she is the Jane Goodall of millennial women as a former editor in chief of 17 Magazine, Ann was able to lead editorial that was authentic to young women’s evolving values and push the boundaries of digital print and crop digital print andcross-platformm content. She has been named one of the most powerful us fashion magazine editors by Forbes. She is the author of The Big life, she leads a community of bad ass babes both on and offline. She works tirelessly to shape our conversation about the power of millennial women. I first met Ann at the Soho house here in New York about two years ago. Of all the networking events and book talks, and all the kinds of things I like to go to here in New York, she really just stuck with me. I was so impressed by her authenticity and relatability and inspiration. So, ever since I have really followed her, I love her book, The Big life and, Ann, as I said, you’re such a big role model to me. This is one of my big life moments. So, thank you so much for being here.


Ann Shoket: Well I am so excited to be here, and of course I remember meeting you. You’ve hosted a badass babes dinner, right? I skyped into one of your dinners, which was so amazing. You had all these women gathered around your apartment, like, women everywhere. So I am thrilled to do this for you and to be part of your big life and your bad ass babes squad.


Leah Gervais: Great. So yay, thank you all for watching as well, and tuning in. Please let us know where you’re tuning in from. I love hearing where everyone’s located. Okay, so Ann you were the editor in chief of 17 magazine for the better part of a decade, and so seeing all you did you know, what would, in a short answer, I’m sure you could talk on and on about this, but, what is so profound about millennial women in comparison to the generations about us?


Ann Shoket: So, when I was at 17, I started there in 2007, and so it was the year of Lauren Conrad and everyone wanted to be blonde and tan and drive their Mercedes SUV through Southern California. Then, we have a terrible recession, right. So suddenly, the Mercedes was a fantasy. Instead of like, you know, going out for frappuccinos we were making our cappuccinos at home and shopping in our closets, and it was a real drag. But, I became like, acutely aware that it was a defining time for this generation of young women. That young women who were just coming into their own when the financial rug pulled out from underneath them and their families. They reacted rather than sort of retreat or stick with the status quo or get lower paying jobs. They reacted to this moment with tremendous ambition and drive. It was it was a radical departure from where we’ve been right. We’ve been in this moment of

Lindsay Lohan and Paris Hilton, and the rise of the Kardashians that are in the early 2000s, right. I mean, it’s like, it’s so crazy to even think about it. Now, this so worship fullness of wealth and flash, right, in a way that we just don’t have now.


Ann Shoket: It was a total reset, and now we’ve replaced all of that. We’ve replaced it with worship fullness of success and power and influence. That this generation of young women got motivated to achieve and succeed. And, you know, there’s a lot of other pieces at play too, like the rise of social media. Where you have control over your message. Here you are at your side hustle, you’ve put together a business of women there, you have a platform to say what you want to say to the world, we didn’t have that in 2007, right? You like a post, it’s so crazy to me, when I see my Facebook, like, you know, the memories they show you. They are like, they show me memories from 2007, or 2008 or 2009. And my memories are like, um, like a text status update, like you couldn’t even put a picture, right?


Leah Gervais: Yeah, what are you doing?


Ann Shoket: Yeah, and it’s something crazy. So the all of those pieces came together to be this amazing, amazing ingredient for solution that is being led by women.


Ann Shoket: I mean, I have the honor of being the editor 17 at such an important time, and to be there talking about things that matter to young women, and to feed those dreams you had about how your life was going to be bigger and more meaningful and different than the generation of women who came before you. So that’s where the big life comes in. When I left, I knew I wanted to continue this conversation with young women talking about the things that matter in their life. So, I wanted to move into the next phase of your life. You know, I’d spent all this time saying like, here are your dreams, let’s work on them together. Then, like, this is the guidebook for getting those dreams. And that’s what The Big Life is about.


Leah Gervais: I love that. I love it. I love the book. That all resonates so much with me, with some PTSD from the recession of how our generation handled it. So, I want to pick out one part of The Big Life, the part that my platform is really all about, which is this piece on side hustling and our generation all about, you know, having multi-passions having multiple streams of income. So, I know you have a chapter in your book about it. I know you know how relevant it is, and I guess, what advice do you have about it? What do you see both as a you know, cheerleader for millennial women who you so badly want to succeed, and also a former employer, and do those contradict? I’d love to hear your take on it.


Ann Shoket: So the side hustle is like the most important thing that you can do. So when we get started in the world, you have to get a job, get a job, any job that’s chapter, I think that’s chapter two, right? Get a job, any job and you have to learn how the world works. You have to understand yourself, you have to learn like, do I like to work solo, do I like to work in an office do I want to have flexible hours? But, I much prefer to like, go to work, do my job, come home. You need to understand how work works. And so get a job, any job but, that’s just to pay your bills, right? To learn how the world works, and to pay your bills because you got to pay your bills and that student debt. But the side hustle fills in the blanks for what your job is not giving you and like, let’s be honest, we’ve moved beyond this idea that your job can be everything for you.

As much as we work on work and life coming together, it still can’t be everything, and so your side hustle fills in those blanks. What are you missing? Are you missing community? Than your side hustle needs to give you a community are you missing meaning? Do you have a job that just isn’t like you’re learning, it’s fine, whatever. But it’s not like it’s not speaking to your heart. Your side hustle needs to speak to heart. Are you not in charge in your day job, and you want to have something of your own? That’s what you’re side hustle is.

So when I was coming up in the world, we didn’t even have the term or phrase “side hustle”, though, I had a side hustle. I was an assistant at the American lawyer magazine. And so I filed reports and answered the phone, and ordered tuna salad for my boss, and tried really hard not to get fired. And I really was like, just like nuts and bolts of learning how to be a reporter actually, and it wasn’t very fulfilling. So it was actually the beginning of the internet, and I launched my own website. It was like this indie, cool, downtown website, and it was like, by day I was an assistant, and at night I was editor in chief. I’ll tell you the truth. The things that I learned by being editor in chief of my own side hustle in 1996, was, I know sounds like a million years ago.


Leah Gervais: Oh, no, no, no, I think it’s awesome that you were launching a website and everything.


Ann Shoket: Um, yeah, the internet. We didn’t even have like, I don’t even know it was 1996. I don’t know.But the the things I learned are still things that I use today. Like, I learned how to manage a team. I learned how to motivate people, I screwed up how to motivate people, I always screwed up how to manage a team. I didn’t know what people were interested in reading, and I figured it out. All of those things that I learned by figuring out business on my own are still things that I to this day, use and frankly, it helped me get ahead in my business the same way you’re going to use your side hustle. Now, it gives you something more interesting to talk about it a meeting, right? Like, yeah, yeah, I really I did my work it’s excellent. But let me tell you about this passion project I have where I learned X, Y and Z or I have access to so and so. Or like, this thing that like, you know, is interesting to your company. But you can’t get them to let you do it. So now you just do it on your own steam.


Leah Gervais: That’s awesome. I love that definition of it. I couldn’t agree more everything you said.


Ann Shoket: I don’t know what your day job is, can you say what your day job is? Does everybody else out there watching know what watching what your day job is?


Leah Gervais: Yeah, my day job is, I I love my day job. I work in a nonprofit. I work with foundations in New York and we do a lot of work locally and nationally. We do a lot of professional development and I mean that’s why I’ve stayed there is because I actually love it which how often do you hear that in New York? You know? Not very much.


Ann Shoket: And so your side hustle lets you explore editorial, lets you figure out a new tribe of people that you want to work with. Let’s you be the boss.


Leah Gervais: Yeah, I mean, all of the above, I’ve had such a journey that has gotten me to where I’m at right now with it. And, you know, really growing it to where I make even more from it. Now, then I make from my day job, which was definitely not really thought it was going to be, I thought that I was going to kind of have this for fun blog while I was going through a confusing time in life. So seeing it grow. I mean, the whole reason I started it was because I wanted to start a platform for, you know, 20 somethings or 30 somethings that were going through what I call a quarter life trap, which is not where things are bad, you know, nothing’s bad. But it’s where things are fine. And how easy it is to get stuck in that just like Limbo and stay stagnant because you have a decent job. Because, you know, like I had, I had a boyfriend because I like living in New York, things weren’t bad. But I wasn’t really fulfilled. And I was so lost toward what that meant. I had no idea what I was going to do. I didn’t know what I wanted my career to be. So I quit my job and traveled for a while by myself, and kind of like, Eat, Pray, Love, if you will. And so I started my website to be a blog basically, to, to share with other people that, you know, they’re not alone. If they’re feeling lost, they’re not alone. If they don’t know what they want to do with their life. They’re not alone if they want to travel alone. And as I learned more and more how to make money online, how to, you know, have a gap in your resume, how to do all these things that basically I was told I shouldn’t do, and I sort of did anyway, then I started writing more about it, and then I started monetizing it. And so seeing it grow, and just seeing the, the need for what I originally, what I originally was suffering with, has been the most rewarding thing of my life. And for a while, you know, on the surface, the, what you’re saying about purpose resonates with me so much because I thought, you know, I work at a nonprofit that on paper is full of purpose. You know, it’s so easy to help people. But what I think is sort of my zone of genius, or what I love the most is helping people make the most of themselves, and that’s not what I do with my side hustle every day. So it’s just, you know, at first I was like, am I really going to, you know, work around my nonprofit, like just posting things on social media, you know, it can seem a little bit like, not as prestigious? But it’s so much more than that. And I just took me a while to really find that, that’s awesome.


Ann Shoket: I’m glad that it’s like, turned into like, a money making business for you. It’s amazing.


Leah Gervais: Thank you. Yes, it’s been absolutely incredible,


Ann Shoket: A side hustle doesn’t have to though. I don’t want everybody to think that like your side hustle has to be a business, right? I mean, it is great, if it does, right? It provides you with an off ramp. But the important piece of your side, hustle is not making money, it’s paying yourself and self respect.


Leah Gervais: I love that, and I couldn’t agree more. That’s beautiful. And that takes the pressure off of it because what’s so great about having a side hustle is that you, you know, you have a day job, you’re not needing to make money, you’re not relying on it. So that desperation doesn’t come out and you like it can a lot of young entrepreneurs. So that’s what’s so I think incredible about the opportunity. There’s low, you know, overhead costs, and you have your day job money. You know, I know, it’s not the easiest thing to juggle it all. But like, it’s not like, you’re not going to know where your next paycheck is coming from. So you have this room to experiment with yourself with your business with what you’re interested in. That’s just remarkable. And especially when you’re young, and you don’t have a mortgage or kids. I mean, I think that everyone should take this opportunity.


I want to ask you a question a little related to this, I know that you didn’t, you know, start the big life while you were editor in chief of 17 magazine. Your progression was quite different than people starting a side hustle and making it their full time job. But do you have any advice or things that you want to share about that transition of a very structured nine to five, you know, 17 is a big organization within a big organization to now you’re a full time entrepreneur.


Ann Shoket: Yeah. So, the biggest personal thing for me was to recognize that I had something to say, and I didn’t need a brand to say it, right? But that being at 17, it was always about what’s right for the brand and what’s right, and that was my job. That’s I mean, that’s a tremendous honor. But that separate from 17, what I brought to the conversation, the way that I envisioned that magazine and shaped that brand for so many years. I needed to figure out what pieces of that were me and what was 17 and it took me a minute. But the thing that was so grounding for me, and that was so clarifying was what unites us are these universal feelings of wanting to make our mark on the world. Wanting to do something so big, so badly, and not knowing where to start that, to read it, to know that you have the power inside yourself, and to not be able to figure out how to have that expressed to the world, particularly when I hear from so many young women, that they that they see obstacles in their way, right. They see people who don’t support them, bosses who aren’t interested in like moving them forward, people who see them as transactional cogs to just fit in the wheel of work, rather than see them as human beings with something amazing to contribute and to nurture their growth in the world. And beyond career, also, the way young women see life and love and money and sex differently. So first of all, it was very freeing for me to be able to talk about life and love and grown up things about sex. That was kind of like a base. That was like, a nice thing for me to be able to grow with you into the next phase of your life.

But the shift from being a big brand to being a personal brand is different. It’s different. It’s I don’t know how to say it. There are great benefits to both, right? There’s a lot of benefits to be the big brand. But it’s so rewarding to know that I have a direct connection with my audience and with my tribe and my bad aspects. Are you all, is everybody who’s watching signed up to be a badass babe?


Leah Gervais: Would you like me to drop the big Facebook group or the email sign up below this?


Ann Shoket: Sign up for the newsletter, sign up for the Facebook group.


Leah Gervais: I love her newsletters every Friday. Um, okay, awesome. Yeah, I’m sure I’m sure it’s, you know, completely different. And you’ve kind of had the extremes of both where you’ve really had a personal brand and where you really worked at a huge tense. So I’m sure you’ve seen the contrast. But I think that it can feel, you know, I think that that the difference is sometimes bigger than we give it credit for, especially for younger women who haven’t been in a career as long they might think, Oh, well, it’s not going to be all that different. I’m just going to work for myself. I think that the difference is a little more dramatic than we might think.


Ann Shoket: I mean, so it’s funny, like, all the things about working for yourself that are different are, you know, like, you have to build your own tribe in your own community. You have to find the people around you. It’s not kind of built in, who are the people who work with you and work for you, right? You know, you have to be rigorous about your time and your attention and your energy, which is so important, right? You could find yourself completely tapped out in the wrong direction, because your days are your own. But I find that the thread that’s so important to me is that I have a mission and a mission when I was networking team, but I have a mission. Now a mission is to help young women find their power and to make the world recognize it, too. I am of service, right? It’s not that the peak of what I’m doing is not just about like, oh, it’s make sure I can show right that I am of service to my audience, my tribe, and that’s what’s so important in the conversations that you and I are having the conversations that I have in my newsletter, and that we have in the Facebook group, that’s deep, important stuff. It’s not like, I’m not coming in and saying, Hey, you guys, like, I totally have this stuff figured out. Let me just tell you how it goes, right? Like I’m saying, we are in this together. I have some perspective, and a little bit of distance from some of from some of it, but I feel the changes that are happening in the world just as acutely as you do.


Leah Gervais: Right, right. I have a money question. Do you have advice for people that are nervous about going from having a consistent income to then not knowing how much they’re going to make each month or each week? I think that that’s one of the biggest reasons people don’t jump from their side hustle to their full time hustle, because that’s so scary. How do you make it less scary?


Ann Shoket: Okay, it’s scary. You got to pay your bills. And you need the safety. There’s no making it less scary. That’s why you need that safety net. Like, what do you want to do? Like, move home with your parents or like, ask your boyfriend? No, we’re not doing that. That’s not how it goes. This is you and your dream and your career and your pendants. And so you leave one job that pays a lot of money to go to something that doesn’t pay a lot of money unless you have a lot of money in the bank. Right?


Leah Gervais: Right. Right. Yep. This very simple answer. But I think what you said is so important about you know, it’s still going I think, and what I’ve even seen from friends in New York that have done this is even when they have six figures in the bank, it can still be scary. So recognizing from the beginning that the fear isn’t going to go away, you’re always going to feel that pressure and trying to move forward with it. Instead of waiting to no longer be afraid because that’s never going to happen and then you’re never going to quit your job or really do anything.


Ann Shoket: I did a talk recently with a woman who I really respect who founded stash wealth, Priya Malani. She’s an investment advisor, right? And she’s young. She talked about building that safety net and working on things that are important. I’m not playing for business, I don’t know anything about her business. But I listen to people who are super dialed into that piece of the finance equation. And that, yeah, that the money that you are making and demanding equal pay, frankly, or that, who cares if it’s equal, just demand a lot of pay and that money is freedom, right? It’s not about it’s not about buying handbags or shoes or anything. It’s freedom to know that your rent is paid, right? Your bills are paid, your student loans are paid, and that you have space in your life to do the things that matter to you. Because other because that’s not taking care of you can’t you have to do the things that matter somebody else?


Leah Gervais: Right, right. Great. Okay. So we only have a couple minutes left in this has been amazing. But I want to ask you a final question to make sure we get it in. So I guess what’s the number one piece of advice you’d give millennial women. And in my bias, especially those beside hustlers you’ve given us so much. But if you have like one big takeaway, or I always like to ask what you would have told yourself 10 years ago, or 20 years ago, however long you want to go.


Ann Shoket: Forget about the things that you should do, and focus on the things that you want to do. You said it in the beginning about this path, right? You said that you’re on you’re on a track. And it’s easier to be on a track it feels like some decisions are made for you. Or at least the decisions are narrow down to two choices, this or that. East Coast, West Coast, big company, small company, but the things you should do or somebody else’s idea of what it means to live the big life and the big life is life on your terms. It’s about crafting a vision and going for it and putting the pieces together and strategizing around it. Most importantly, finding a tribe of women, a sisterhood of women who are going to be in it with you and we’re more than just supportive and encouraging we’re going to help you work through the nuts and bolts of moving ahead in the world and so forget about the should’s is the most important piece the best message.


Leah Gervais: Incredible great alright well thank you so so much. Do you have anything you want to leave us with or I think that that’s pretty much what the mic drop is.


Ann Shoket: You know I would love to stay in touch with everybody who’s watching please sign up for the badass babes. Facebook and I would love for you all have your own copy of The Big Life. I’m excited, I love this book. I love talking about it. It’s really when you tell me that it resonated with you and that maybe I went with you on vacation or on top of your nightstand or that there are women who can message me and say they read the book more than once and go back to passages they’ve underlined. think there’s nothing more amazing than that. And so I thank you for that. But I would love for everybody. Spread the word. Life on your own terms.


Leah Gervais: That comment said they reread it all the time.


Ann Shoket: So thank you.


Leah Gervais: All right. Well, thank you so much. And I hope you have a fabulous weekend and everyone that’s watching you can find her group and what I posted and as I get off I’ll post her website as well so you can sign up and I will see you guys in her facebook group. Thank you so much Ann.

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