A Conversation with Wendy Sachs

It seems appropriate to kick off this New Year with stories and words of empowerment. My dear friend from college, Wendy Sachs, has written a book Fearless and Free: How Smart Women Pivot--and Relaunch Their Careers -- to be released by AMACOM on February 7th -- with the aim of emboldening women and infusing them with confidence as they navigate the workplace and their personal lives. With the Women's March on Washington happening this weekend, it could not be more timely!

You can read our conversation below, in which she offers some great tips and tools that you can apply right away. I hope that any readers might also consider passing this along to your female counterparts!

WENDY SACHS is an Emmy award-winning network television producer, former Capitol Hill press secretary, editor-in-chief of Care.com, media relations executive, and the author of Fearless and Free: How Smart Women Pivot and Relaunch their CareersThe book will be published by AMACOM in February 2017. 

Wendy is also the author of the critically acclaimed book on balancing career and family, How She Really Does It: Secrets of Successful Stay-at-Work Moms (Da Capo, 2005). 

As a media executive, Wendy has represented companies ranging from tech start-ups to NBC Universal. Through the lens of smart storytelling, Wendy effectively connects with audiences and grows the awareness of an individual, a business or a brand.

A journalist and blogger, Wendy is an expert on work/life issues and has appeared on dozens of radio and TV shows including: NBC's "Today" show, ABC's "Good Morning America," MSNBC, CBS, FOX News, CNN's "Headline News" and others. She is a contributor to CNN.com and the Huffington Post and has written for the New York Times and several magazines.


Karin: How did your new book 'Fearless and Free' come about? 

Wendy: So I've had ten thousand jobs, so that's what really inspired this book. I just keep trying to stay relevant. I mean, the whole point of my book is that I've been hustling, because as the media and technology have disrupted careers over the past five years, it's really blown up everything; so many people in media and traditional media lost their jobs. It's all about social media; everyone's really young with millennials entering the workforce now and everyone being so much cheaper to hire than me. I have been interviewing, going into social media firms, looking around - what's hot, what's growing. Just trying to stay in the game and also realizing everyone who's interviewing me is 29 years old. It's the craziest phenomena; everyone for an entire year, every interview I had was by someone who graduated from college in 2009. And I kept doing the math, and I was like, what is with that?

So all of this had been marinating my head. What do we need to do to stay relevant? How do women, particularly the Gen-Xers - women who've taken themselves out of the workforce and are trying to get them back in - what can we do? How do you get a job? And how do you stay current and do something that is still marketable? How do we re-brand ourselves?

Where did you go to find the answers?

So I started looking at technology. I'm very into technology and the Silicon Valley companies that blow up and get huge. What are the secrets there? I started looking at lessons of the Silicon Valley - like these founders whose companies totally fail, then get hired to run new companies because the venture capitalists are investing not in the company but the people. So that's interesting - how do we get someone to invest in me again?

So then there's the idea that women don't take risks the way men do. And we suffer from more inertia because we want it to be perfect and we're afraid of failure and we only apply for jobs if we feel like we have 100 percent of the credentials; where studies show that men apply for jobs if they have 60 percent of the credentials. And how do we engineer our own serendipity? That's a big theme in Silicon Valley and a lot of creative agencies - they literally create cultures where serendipity can be manufactured. It's not just a happy accident that great things happen but it's like a collision of creatives. So how do we create that energy for ourselves? How do we learn to network better? Those were sort of all the themes that I started looking at.

What kind of tools, tips and advice do you offer women?

Women don't like to brag about themselves, they don't like to boast. So there's a new book that came out, Jessica Bennett's Feminist Fight Club that talks about having a 'Boast Bitch'. Everyone needs a Boast Bitch, someone to do it for you. It's super helpful, even if it's your mother -- anyone who is your person, who can help elevate you. Our friend Nikki is my boast bitch; when I have an article that comes out she's the one who posts, she's the one who brags about it.

That's the only reason I know about your book!

That's exactly right, and it works. It's really interesting.

So how do we amplify each others' voices? The Washington Post talked about this; with the women in the White House who realized in the early years of the Obama administration they were being left out of meetings. President Obama would ignore the women in the meetings. They weren't being included.

That's so surprising.

Yeah right, really interesting. So they got together and said, “OK so when Anna makes a point, we're all going to reiterate it and bring it back to Anna.” It's about saying, “As Anna pointed out earlier, I totally agree with that.” And they realized it worked. It was really subtle. They call it “The Amplification Effect.” And then Obama started actually asking these women directly more; he probably didn't even realize the unconscious bias that was happening.

So all of these small things are actually big things.

And then how do we also get out of our own small worlds? We know who we know, but it's about making the 'adjacent' possible. So you're reaching, you're pushing out of your comfort zone. You're going to places, new networking events that you wouldn't necessarily be going to, and you start expanding your circles.

I know you have a chapter devoted to your experiences of getting fired. How does that relate to the themes you're exploring?

This goes along with that whole embracing failure and the failure fetish of Silicon Valley. So these guys are either fired or their companies blow up, and yet they keep going on. I interviewed a few high-profile women aside from talking about my own firing. Jill Abramson from the New York Times, who is the first and only female executive editor - top of the mantle at the Times - was very publicly fired two years ago. They just didn't like her. She'd been at the Times forever, and before that, The Washington Post. She is now teaching at Harvard, and she gave a very well-known commencement speech at Wake Forest days after she was fired. They assumed that she was not going to want to do it. She was like, “Hell yeah, I'm doing this. I'm not going down thinking that they kicked me to the curb and I'm done” and she gave this amazing speech. Now she's at Harvard doing a big book with a million dollar book deal - and she's 62 years old.

And the woman who is the founder of Girls Who Code - Reshma Saujani - she's incredible. She's everywhere now; she's doing TED talks and all of that. But she ran for Congress and lost in a landslide. She ran again for public advocate in New York, lost again in a landslide. She ran for something else, lost. She applied to Yale Law School three times before she got accepted. She has an incredible story. And then she founded Girls Who Code a few years ago, and it just took off. So the theme is almost “lean into failure.” Not that we want to fail so bad that it just destroys our souls. But how do you grow from it? Not to be so afraid. It's all in the risk-taking where we grow confident. So the biggest piece... there's a chapter on confidence... is how do we become more confident? How do we let ourselves take risks? Because you need to take some risks to move forward and to grow and to not be so scared and to be OK that it fails. And to move on from it. There are plenty of things that I have failed at, aside from just getting fired, just other endeavors - documentaries I've tried to make, another book I tried to write. Things that just don't happen.

What is fascinating is that I have friends who always assume, “It all works out for me.” I'm like, “You don't get it. You're not seeing all of the failures; you're just seeing the success. You don't understand all of this hard work that goes into it. For two years now I've been working on a book.” Most people didn't know for two years I was working on a book; it took me nine months to write a book proposal, and I was working a full-time job at the time. So they only see me with the headline, or whatever, I put out on Facebook; they don't see all the blood sweat and tears that go into it. And that's what it takes; none of it is easy.

Are you suggesting that some people only see the successes in their lives and don't acknowledge their failures?

I think that we live in a world of Instagram and Facebook where everything has a filter on it. And so there's a lot of Facebook envy and stuff like that that happens, until you start peeling off the layers. That's why I love the women in my book - on the one hand, look at this woman Reshma who's beautiful and she's 40 years old and she's a TED speaker. And she has a book out and she's running Girls Who Code which is an incredible organization with ambitious goals of getting women and girls coding - like a million of them coding - in the next few years. It's like, wow, it's total unicorns and sunshine. And then she talks about her miscarriages as she's running for office, and her huge failure when she ran for office, how humiliated she felt, and just all of the stuff that went in. And you're like, “Wow, and you still pulled through, you rose from the ashes. That's extraordinary.” And so, I think it's understanding what success looks like. It can be really small, too, the little steps that you take to move forward. You should be proud. You should be celebrating.

Also, I think that our generation - certainly our mother's generation - as we were coming up through the workforce, we really felt like there was only a small space for women at the top. We weren't really raising each other with us. I don't want to say we were climbing over each other; I don't think anyone was that aggressive. But I don't think we were actively lifting each other. I think we were out there on our own, all sort of scrambling to get ahead. And now there's more of a movement, a sisterhood, of knowing that we should be raising each other together, which is almost a millennial type of a thing that's happening. I talk about that, too - the importance that there's plenty of room for cream at the top. There's plenty of space for all of us.

I even thought that when my first book came out. There were a few other books coming up at the same time and I was really upset by that. I was like, “Oh my god, they're going to get all the attention,” rather than realizing, “Why don't I reach out to these authors? Maybe we could figure out ways to team up together and do events together. We're stronger in numbers.” So there's a whole other movement happening.

In this chapter I have on networking, one of the women I interviewed is Shelley Zalis. She's Los Angeles-based; she's amazing, you may know her. She was the CEO of a research company for a long time, sold her business and made $80 million selling her business. A few years ago she launched something called The Girls' Lounge, which has gotten a lot of attention. The Girls' Lounge emerged when she would go to conferences like CES (Consumer Electronics Show) and Cannes and she would feel so incredibly alone; it was an all boys' club type of thing. So she sent out a note at CES maybe five or six years ago and mentioned this whole Girls' Lounge and word got out and she invited everyone to come to her hotel room. And then it grew and grew and grew to like a hundred women, and she got into a bigger suite. They all walked the floor of CES together; it was like “power of the pack” and it has launched this whole Girls' Lounge thing for her. She does these pop-up girls' lounges at these big news conferences now.

They'll do makeovers and they do silly girl stuff, but they also are doing empowerment messaging and it's a space for women, now evolving into something bigger. And soon, because her background is in research, she's coming out with this handbook of equality in the workplace. She has really become very big with gender parity in the workforce and raising women, and the power of all of that, which is a super timely thing that's happening because corporate America realizes they're losing all this female talent and they're trying to integrate women back, and they're trying retain women so they don't leave when they become moms. There's a huge movement to have more gender diversity because the past 10 years we've seen a huge loss of it. So I write about that, too, because that's a piece of my old book also - what happens when women leave the workforce? Now they're trying to re-enter and what are companies doing?

You mentioned that millennials have a different way with each other as women. Can you explain that more?

Well, I think that there's more of an awareness of a sisterhood. First of all, I think with millennials there's definitely arguably more of a sense of entitlement. They want what they want. And they're expecting that when they have kids, they'll still work and they're going to work on their own terms; that the workforce will figure it out for them and they will have to accommodate them. They also don't want to work their asses off the way we did and they want more balance and they're expecting their partners to be taking paternity leave and standing up for that. And they're much more culturally sensitive to having a diverse workforce and color in their workforce, and all these things that I think most white women weren't really paying attention to, like, “Oh, where are the black people?” No one was really saying that. “Where are the Hispanic people? Where are the lesbians?” Now in any office, gender diversity and just diversity in general is very much a focus.

The reality though is that a lot of dads are still not home at night, and women are the ones who generally slow down their careers. But as Shelley Zalis said, “The rules didn't work for me. So I changed the rules to accommodate me.” She went out and created her own company. She'd worked for Nielsen for a while and then another company and then created her own. She has three kids and she had a very family-focused culture and the business did really well and she was able to sell it for 80 million dollars. So her changing the rules to work for her and to make it more family-friendly didn't hurt the bottom line, it didn't hinder her. It grew her business because people are happy and there was loyalty and people didn't leave.

You know, there are all different pieces to it. It's about becoming more confident; it's also about how we present. I don't know if you followed this whole 'sorry, not sorry' thing over the past year. There's a lot of emphasis on women apologizing; women apologize all the time. Panteen did a great ad about it and then this woman came up with this G-mail plug that will scrub your e-mail, basically alert you like a spell check every time you say “sorry” or “just” or “actually” - different, what they call “shrinker” words where we're hedging a bit because we don't want to come off too strong, because we don't want to come off as too bitchy. So I'm really hyper aware now about how I talk.

I see you as quite direct and confident and bold with your language and your presentation. So really, even Wendy has to work on this?

Oh God, yeah, we all do. What happened was... while my boss really liked me, other people didn't. I was working virtually; the company was based in Boston I was in New York, and so I would have a lot of phone calls and conference calls and she knew me in person and we got along beautifully. But she said, “People think you're a little too brash, can you just dial it back? They're not seeing you smile and they're not seeing your body language.” In person I'm very touchy and I'll touch you. In any case, it was a technology company I was working at; it was a startup. And there are all these studies about how women are really scrutinized at tech companies and startups, and in the reviews there are words like “brash” and “bitchy” and this is very, very common. She even told me - and it was a woman CEO - to keep my head down. And I thought, “Really?” By the way I was the editor-in-chief, the spokesperson for the company. I was going on TV talking about the company. Why would I be keeping my head down and why can't I just be direct?

But when women are direct, like Hillary Clinton - I write about Hillary Clinton a lot in this chapter - we're not well-liked; it's this whole double-bind that women face. The double-bind is that if you come off as too smart and too direct, you're not well-liked. If you're well-liked as a woman, you're not thought of as really smart and a leader - all those leadership qualities that we seek in men. Even Bernie Sanders who could be pounding the podium and thrusting his finger... Hillary Clinton was criticized for not smiling enough. No one was telling Bernie to smile. And that's the double bind that women face. So after that experience where I was told, “You're too this, you're too that. We think you're really smart, but it's a personality thing.” I was so horrified, so heartbroken. I couldn't believe people thought I was such an asshole. And so, at my next job I started doing what one of my friends/colleagues would do. I write about her... she's blonde and she's petite and she would say, “sorry, sorry, sorry” and it really worked for her. And so I started adopting this whole “sorry” thing. I was working at a company called Grey Advertising, which is a big global agency. There I was with hot shot ad guys, it's totally Mad Men, and they have huge egos and I would just be like, “Sorry, can I ask you a question, sorry.” I was apologizing for just being there and taking up space. It was crazy, but it worked really well. And no one thought I was arrogant. I was much more passive. I was not really myself but no one thought that I was mean. I was working in this content division, and ironically, they did the “Sorry” Pantene ad. When I was there the ad came out, and I was like, “Okay, I'm done with sorry.” So women have this double bind. What is it that we can do? How can we be perceived as warm enough and nice enough, but also leaders?

So I give some tips that I got from other people. Even in an e-mail, how you can come across as warm and friendly - like you open and close your e-mails with some warmth and some connection but scrub the “just” and “actually,” and never apologize in an e-mail, even if you did something really wrong. Pick up the phone and call - you don't want to have an e-mail trail; certain things that we should just know. And then funny enough, my friend, the blonde pretty, cute, petite girl who would say “sorry” - I interviewed her about all of her sorry's and she said she started dropping that too because it was pointed out to her by one of her colleagues that she was apologizing all the time. He said, “Don't apologize, you haven't done anything wrong. You've got to stop that.” He was giving her good critical advice, you know, a more senior person, and he said, “You're even apologizing for things you haven't done.” But that was her mechanism, to deflect, fall on the sword, basically, take the blame even when she wasn't responsible because she wanted to calm everyone down. So there are lots of good takeaways.

It's really very much about trying to empower women, pulling all the layers off of all the different elements of what we need to do from how we can grow confidence in 'how we present ourselves with confidence' to 'how we fake it until we make it confidence'. Some of that is pretending a little bit until you own it. For people who are afraid to get up in front of an audience, you just have to keep getting up until you master that a little bit more. So you fake it at first and then it becomes more natural and then you get it. It's about taking those risks, creating moments of opportunity, and filling in the gaps when we need to.


To learn more about Wendy Sachs, visit wendysachs.com

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