Fearless and Free: How Smart Women Pivot and Relaunch Their Careers

Fearless and Free: How Smart Women Pivot and Relaunch Their Careers

by Wendy Sachs

ISBN: 9780814437698

Publisher AMACOM

Published in Self-Help/Success, Business & Investing/Women & Business, Business & Investing/Personal Finance

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Sample Chapter



Boost Your Brand

"Your time is now. Work on purpose and with purpose. Never get stuck. Pursue your passions. Make bold moves. Beware the status quo. Leave a gentle footprint."


I'm standing fifty-person deep in a line snaking down the block at sweetgreen, a farm-to-table, on-the-go salad shop in the Flatiron area of New York City. The sweetgreen manifesto hangs prominently near the entrance, an inspirational beacon beckoning us into a fragrant store filled with organic kale and humanely raised, hormone-free roasted chicken. I come to sweetgreen and endure the wait not only because of the locally sourced produce, but also because of the vibe. There's something uplifting amidst the spicy sunflower seeds and baked falafel balls. The sustainability-meets-SoulCycle empowerment message resonates with me. "Our delicious and healthy food aligns with your values," reads the "Our Story" page on the sweetgreen website.

Today every brand, like every comic book superhero, has an origin story — from Warby Parker eyeglasses to TOMS shoes to the quinoa I'm consuming at sweetgreen. We women each have our stories too. We need to define them, own them, and sell them. Most of us aren't walking around with a personal manifesto tattooed on our backs, so how we present ourselves to the world, not only in person but also online, has tremendous impact. We know our LinkedIn profiles and curated social feeds represent what we stand for and care about. We may be cautious or even precious about what we post, wanting to craft a certain image. But there is another piece to how we outwardly present ourselves and control our message — and it's as obvious as it is subtle. The language we use in person and in email sets a tone, and in just a few words it can convey our confidence or our insecurity. What we think may be a friendly, conversational style can inadvertently be harming us. Without realizing it, we women sometimes sabotage ourselves, our brand identity, and our professional currency with small words and phrases that qualify what we say and diminish our power before we even begin.


"Sorry." It's a word that my dear friend and former colleague Jo Flattery, forty-three, a smart, seasoned, incredibly likable PR maven in New York City, used to use a lot. It worked for her. "It can take the tension out of the room," Jo tells me as we sit eating our sweetgreen salads.

Jo has a warm, earthy vibe that is as disarming as it is honest. She is masterful at scoring major press hits but is equally astute at assuaging combustible egos. Jo's former boss would bring her to meetings with the tough clients because she is intuitively skilled at making alpha males a little softer and gentler. "I am the pony that cools down the horses. I am a Gemini and a middle child and am always looking to make the peace," Jo says smiling, dimples flashing.

Jo's style is unfiltered, but not brash. After years of listening to Jo use "sorry" as a way to deflect seeming too forward, I started using it. It worked like a charm. It was a lovely social lubricant that made what I say silkier, softer — perhaps easier to digest. A few years earlier I had left a job at a start-up where my boss had told me I came off as too abrasive. Because I worked remotely in New York and the company was based in Boston, much of my communication with my colleagues was over the phone. "They just don't see the real you," my boss would tell me. "They don't know you like I do and see your smile or your body language." It was supposed to be professional constructive criticism, but it felt personal.

Feeling insecure about how I was being perceived at work, I began trying out Jo's "sorry." People never accused Jo of being bitchy or abrasive. Was it because she was blonde and petite? Or was it the language she used? Maybe it was a little of both. So I started apologizing.

I got a new gig at Grey advertising and took my "sorry approach" with me. I was working with a lot of young hotshot guys, and it easily slipped into my vernacular. No one seemed turned off or threatened by my direct approach or accused me of being bossy because, well, maybe I wasn't so direct anymore. My "sorry" became almost deferential: "Sorry, how do I share my plan with the team?" It became my way into conversation. "Sorry, can I ask you a question?" Ironically, a shampoo ad produced by Grey while I was working there immediately ended my apologizing. I was now suddenly sorry for using "sorry."

The Pantene ad that launched in 2014 shows how women use the apology as a subconscious technique to downplay power or to soften what they want to say. In the ad, we see women in different scenarios constantly apologizing. At work, a woman sitting in a conference room looks up and says to a man standing over her, "Can I ask a stupid question?" At home in the kitchen, a mom says "sorry" as she hands her baby over to a man who seems to be her husband. And "sorry" is used with strangers: A man bumps into a woman as he sits down next to her and stretches out. He knocks her knees but she apologizes. A woman gets into a car with a guy who appears to be her friend. They start talking at the same time, the woman says, "Sorry, you go first."

The women apologize not for being rude or hurting someone, but for asking questions and simply taking up space. What I had thought was a breezy approach to engagement suddenly became loaded with lady baggage. "Sorry" isn't just an apology for a screw up, it's also a way to make sure you aren't accused of being bossy, bitchy, or too aggressive. It's filler; it's a crutch; it's a way to appear gentler when you are asking for something. It's a power deflator that sucks the energy away from what you are saying.


Amy Schumer took on the "sorry" state of how women speak in a May 2015 sketch on her show Inside Amy Schumer, where she skewered our propensity to apologize. The scene is set at a "Females in Innovation" conference during a panel with top innovators in their fields, including Schumer as a scientist who studies neuropeptides. The other women on the panel are equally accomplished: There's a Nobel Prize winner, a Pulitzer Prize winner, a woman who invented a solar panel water filtration system, and a woman who built a school for child soldiers. The sketch opens with the panelists apologizing for correcting the male moderator as he introduces each of them incorrectly. He screws up, but the women apologize. Then they apologize for talking over each other. Pretty soon the sketch becomes more ridiculous, devolving into a scene of "sorrys."

"Sorry, I hated that."

"Sorry, I wish I hadn't said that."

"Sorry, is this coffee? Sorry, this is my fault."

At one point a stagehand delivers a cup of coffee to one of the panelists, who had clearly asked for water, saying she's allergic to caffeine. He delivers it anyway and, in the process, spills the coffee on another panelist. The woman writhes in pain on the floor, blood gushes from her legs, and she apologizes. The other women join in. It becomes an absurd symphony of "I'm sorrys," leaving the male moderator completely confused.


Tami Reiss, CEO of tech company Cyrus Innovation, saw this sketch, as did many of the women with her at a brunch for the League of Extraordinary Women. They discussed how they fell into the habit of using these "shrinker" words even though they knew they shouldn't. They also spoke about an article that had recently run in The Washington Post, "Famous Quotes: The Way a Woman Would Have to Say Them in a Meeting." In this spoof, reporter Alexandra Petri gives iconic quotes the lady treatment.

* "Give me liberty, or give me death."

Woman in a meeting: "Dave, if I could, I could just — I just really feel like if we had liberty it would be terrific, and the alternative would just be awful, you know? That's just how it strikes me. I don't know."

* "I have a dream today!"

Woman in a meeting: "I'm sorry, I just had this idea — it's probably crazy, but — look, just as long as we're throwing things out here — I had sort of an idea or vision about maybe the future?"

* "Let my people go."

Woman in a meeting: "Pharaoh, listen, I totally hear where you're coming from on this. I totally do. And I don't want to butt in if you've come to a decision here, but, just, I have to say, would you consider that an argument for maybe releasing these people could conceivably have merit? Or is that already off the table?"

Tami says the conversation about how women are not comfortable being direct is not new to her. At work events, including those that advised women on how to attract business investors, women had been encouraged not to undermine themselves and their businesses with words like "we think" and "we hope to." It was becoming all too obvious that something needed to be done — an effective means of alerting women that they were softening their language when instead they should be speaking directly and with confidence. What if there was something like a spell-check for "sorry," Tami suggested to a friend sitting next to her at a girlfriends' brunch. What if she were to make an online tool that would highlight those trigger words? The women at the brunch loved the idea. One even agreed to do some pro bono PR when it launched.

In December 2015, Tami released the "Just Not Sorry" Gmail plug-in that alerts you when you type certain words including "just," "actually," "sorry," "I think," and "I'm not an expert ..." The plug-in underlines the words as you type. If you hover over the words, it explains how you may be undermining your confidence in your message.

"It's a mindfulness exercise," Tami says. "It makes you conscious of when to use the words and when not to use them. We designed this as an awareness exercise, and we knew it would take off with women."

What surprised Tami was that it took off with the press too. Within a day of its launch, everyone from BBC News and NPR to NBC's Today show was talking about "Just, Not Sorry" and calling Tami for interviews. It struck a nerve.

"This is a way of saying to women, you are consciously stepping in your own way," Tami says. "If your default is to say 'sorry' and use undermining words, by eliminating even half of them, you would be more respected."


No doubt we are in the Zeitgeist of "sorry," and if we needed any more confirmation of its popularity, we need to look no farther than our reigning culture queen, Beyonce. In April 2016, Beyonce released Lemonade, an album with song lyrics wrapped in innuendo that begged for examination. Had Jay-Z really cheated on Bey? Beyonce's song "Sorry," with a literal chorus of "Sorry, I ain't sorry," seemed to be outing her husband's infidelity but making clear that as a fierce and independent woman, Queen Bey would never apologize.

The fiery song inspired Lena Dunham, the actress, writer, and director behind the TV show Girls, to discuss her near-pathological relationship with "sorry." Weeks after the Lemonade debut, on May 25, 2016, Lena Dunham posted a piece on LinkedIn titled "Sorry Not Sorry: My Apology Addiction":

I am a woman who is sometimes right, sometimes wrong but somehow always sorry. And this has never been more clear to me than in the six years since I became a boss. It's hard for many of us to own our power, but as a 24-yearold woman (girl, gal, whatever I was) I felt an acute and dangerous mix of total confidence and the worst imposter syndrome imaginable. I had men more than twice my age for whom I was the final word on the set of Girls, and I had to express my needs and desires clearly to a slew of lawyers, agents, and writers. And while my commitment to my work overrode almost any performance anxiety I had, it didn't override my hardwired instinct to apologize. If I changed my mind, if someone disagreed with me, even if someone else misheard me or made a mistake ... I was so, so sorry.

Perhaps it's telling that Dunham, the Millennial emblem of modern-day feminism and unfiltered fearlessness, is also not immune to the instinct to apologize. It's a habit that plagues even the bravest among us.


All of these "sorrys" do add up, says Tara Mohr, author of Playing Big: Find Your Voice, Your Mission, Your Message. Mohr, a career and personal growth coach, teaches women how to find their voices, ignore their inner critics, and carve out meaningful careers. "Sometimes we say we're sorry out of habit and it's unintentional, but sometimes we do it because we have a sense that we need to soften what we're saying or ensure that we come across as non threatening and as a nice girl," says Mohr. "We are acting out a double bind trying to straddle the middle to make sure we don't offend anyone."

Mohr says research shows we assess a person's warmth in a very quick and immediate way. It's the first thing we size up. We are feeling their vibe. Do we like them or not like them? But competence, on the other hand, is something we ascertain over time.

"It's an evolutionary concept. People are really assessing friend or foe," Mohr says. "We focus on warmth in that first interaction, and then when we are feeling that we like that person, there is more room to demonstrate competence. The key is how to communicate warmth without dumbing yourself down."

Mohr talks about using a bookending approach: Open and close in a warm and personal way in a meeting or over email.

"At the beginning of the meeting, take three to five minutes to chat about the weekend or pets or something to make that human connection, and then show your competence. But close with something warm and friendly to convey your emotional warmth and accessibility," Mohr says.

Navigating work emails, where the goal is to sound friendly but professional, is exactly where all of this can fall apart. Recognizing this, Jo Flattery has changed the way she's communicating online.

"It can be hard to make a personal connection over email," Jo says. "Plus, with the deadline-driven world of news and client management, I found myself apologizing a lot, often when I didn't do anything wrong. It was out of habit. At first I had used it to ease the tension, but then I found myself using it as a transition word. The real lightbulb moment came when I was working on a project and sent a group email to say 'Sorry, here's the situation' about something that I had nothing to do with and which, frankly, wasn't even awful.

"A man on the project, who became a good friend and mentor, called me right away and asked me why I was apologizing for something that didn't even have any merit. And he said, 'Never say you're sorry in an email. Don't create an electronic trail. If you screwed up, it doesn't matter. Just say, here's the situation.' After that, I became much more aware of how easily I would take the fall for something that had nothing to do with me or something that was just totally out of my hands. I stopped intentionally writing 'sorry,' although I find myself still having to delete the occasional 'sorrys' that slip in. When I have to apologize now, I do it in person or I'll pick up the phone. I don't do it over email."

Aside from "sorry," there are other little things that Mohr says minimize our language. Even the smallest words pack tremendous punch and effectively shut down our power. The disclaimers "just," "actually," and "almost" may soften our tone, but they crush our confidence. Mohr recommends scrutinizing your sentences and scrubbing your email for qualifier phrases like "I'm just thinking off the top of my head ..." or "I'm no expert in this, but ..." She says delete the qualifier and just say what you want to say. Also, check for instances of sentences or phrases like "Does this make sense?" and "Do you know what I mean?" You shouldn't imply that you are incoherent. Instead, you can say, "Let me know if you have any questions about this." You can close in a personable way at the end, just don't distract from what you are saying. When the intent of your email is straightforward and clear, you are more likely to get a response.


Much has been made about the double bind that women face. There is considerable research that explores the conundrum, including a 2007 Catalyst study, "The Double-Bind Dilemma for Women in Leadership: Damned If You Do, Doomed If You Don't." The title says it all. Women are in a corner, and it's not the corner office. The study found that women in business are perceived as "too soft, too tough, and never just right." When women conform to gender stereotypes and appear nurturing, they are not viewed as strong leaders. But when women take on typically male leadership traits such as being assertive and direct, they are seen as too strident and not personable.

Excerpted from "Fearless and Free: How Smart Women Pivot and Relaunch Their Careers" by Wendy Sachs. Copyright © 2013 by Wendy Sachs. Excerpted by permission. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher. Excerpts are provided solely for the personal use of visitors to this web site.
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