8 Female Leaders On How To Overcome What’s Holding Women Back

Societal pressure, gender bias, insecurity–these leaders have all felt weighed down at some point. Here’s how they took back the control.

8 Female Leaders On How To Overcome What’s Holding Women Back
[Photo: Flickr user Satish Krishnamurthy]

“Who or what is your worst enemy?” If you ask women leaders this question, you might find a lot of the answers to be “myself.”


It doesn’t matter that we’ve come a long way. We’re educated, we’re climbing–and excelling–in corporate ranks. When you’ve been fighting so hard to get to the top for so long, it’s easy to convince yourself that luck had a hand on your success.

According to authors Katty Kay and Claire Shipman in their book The Confidence Code, women tend to struggle with a lack of confidence disproportionately. When something goes wrong professionally, women blame themselves while crediting others when things go right.

Kay and Shipman also found that women are more likely to be perfectionists and hold themselves back from asking for a raise or even answering a question until they’re 100% sure the outcome will be as they predicted.


So what gives? Why are we so hard on ourselves? Whether it’s gender bias, always having others tell you “no,” or the sickening feeling of inadequacy, eight women leaders below reveal what holds them back–and what they do to keep going regardless.

What Holds Her Back: The Voice In Her Head

Arianna Huffington, President and Editor in Chief of The Huffington Post

“The greatest obstacle for me has been the voice in my head that I call my obnoxious roommate. I wish someone would invent a tape recorder that we could attach to our brains to record everything we tell ourselves. We would realize how important it is to stop this negative self-talk. It means pushing back against our obnoxious roommate with a dose of wisdom,” she says.


“What makes our liberation from these voices harder is that so much of the news and information directed at women these days seems determined to reinforce our obnoxious roommates and make us feel that our lives are somehow lacking. We are constantly made to feel that we should be prettier, thinner, sexier, more successful, make more money, be better moms, better wives, better lovers, et cetera,” explains Huffington.

“Though often wrapped in a “You go, girl!” message, the subtext is clear: We should feel bad because we have fallen short in so many ways from some imagined ideal. Even the very existence of the phrase “having it all,” no matter how it’s debated, is, in effect, implying that we’re somehow not measuring up,” she says.

How She Lets It Go: Owning What She Wants, Jumping In, And Running Fast

Katie Rae, managing director of TechStars Boston and founder of Project 11

Photo courtesy of Project 11

“The most important thing I ever did was own what I wanted instead of listening to other people’s advice,” explains Rae.

“When I left my job at Microsoft I decided to learn how to invest into early stage companies. I learned by doing it and trusting my instincts and then built my expertise over time. Almost everyone I asked advice from told me not to do it so I just stopped listening and jumped in. My style is to jump in and run fast and the more I do it, the more exciting life becomes. You just have to make sure friends are with you in this kind of journey,” she says.

What Holds Her Back: Gender Biases

Sallie Krawcheck, owner of the Ellevate Women’s Network (formerly 85 Broads)


“The reasons women give can be many: “I didn’t ask for the raise’…‘I didn’t ask for the promotion,’…‘I took a flexible position because of family challenges.’ But sometimes it’s not an “I” issue. Subtle gender biases are still alive and well,” Krawcheck says. She shares this example:

For example, some years ago during Managing Director promotions, my team promoted a guy who was described as ‘hard-charging,’ ‘ambitious’ and ‘does what it takes to get it done.’ While he ‘broke some eggs,’ he was a ‘winner.’ The next one up for promotion was a woman: ‘hard-charging,’ ‘ambitious,’ ‘gets it done’ but ‘breaks some eggs along the way.’ Instead of being given the promotion, it was suggested that she get an executive coach to ‘soften her edges.’ It was only when we looked at our notes later that we realized what we had done (and corrected ourselves and gave her the promotion as well).

“Gender biases still exist. Recognizing and relentlessly curbing them yields a superior team and, the research shows, is associated with superior business results,” she says.

“And by shifting the onus of ‘not holding women back’ onto the management teams, we can avoid implicitly pushing everybody to exhibit the same types of workplace characteristics of the existing management team. After all, the benefit of diversity is to actually have diversity,” says Krawcheck


How She Lets It Go: Focus On Things She Can Control

Mei Lee, vice president of digital marketing at Condé Nast

“I follow a method called the 10, 10, 10 rule. When I am faced with a challenge or problem, I would ask myself this question, “How does this affect me in 10 minutes, 10 months, and 10 years?” Lee says. “This resets me and gives me immediate perspective on how I should move forward.”

What Holds Her Back: Fear, Insecurity, Inertia, Money

Rachel Sklar, cofounder of and Change the Ratio

Photo courtesy of

“Fear, insecurity, inertia, money–all those have held me back in my life and still do. I have to fight against it all, and all the time, to put myself out there, and it really sucks when you get that polite rejection letter: ‘We had so many qualified candidates…’ or any other variation on GTFO,” says Sklar.

“But the world will always tell you no if you let it. You have to fight for yes–but when it happens it’s so much more worth it, and you’re so much better. Getting things easily only looks good. Working your ass off to earn something is what actually feels good,” she says.

How She Lets Go: Bump Your Asking Price Up By 20%

Lea Goldman, features and special projects director at Marie Claire


“I think one of the more subtle things women do that holds them back is, literally, undervalue themselves. As women become more open about what they earn–it’s our last taboo, in terms of what we share with our friends–we are beginning to realize just how much less we’re paid than our male counterparts. Seeing the wage gap in stark, black and white can be an eye opener,” says Goldman.

“Part of the problem is that in our efforts to show our passion and commitment for a job or company, we think, well, I should take what they offer me otherwise they will go to someone else. But putting that lower price tag on your head sends a subtle message to your employers that you’re a bargain. I’d rather operate by the principle that you get what you pay for. And I’m worth every penny,” she says.

She explains a solution:


Not long ago I spoke with Stanford biz professor Margaret Neale who said that, when negotiating, you should always (as a rule!) bump up your asking price by 20%–to compensate for the wage gap, yes, but also because of that nasty habit we have of just undervaluing our work. When I share that advice, women always seems stunned. Then it sinks in and you see that moment of revelation.

What Holds Her Back: Societal Decisions

Emily May, cofounder and executive director of the anti-street harassment non-profit Hollaback!

“I think what’s holding women back has less to do with personal decisions, and more to do with societal decisions. The maternity leave policy in the U.S. is one of the worst in developed countries globally. The Violence Against Women Act struggled to pass last year in spite of 1 in 5 women getting sexually assaulted on college campuses. And women leaders can’t take media opportunities without a barrage of comments on their breasts and/or wrinkles. With the deck stacked against us, being a woman leader is an uphill battle and we’re all just trying to navigate it as best we can,” says May.

“If we want to see more women leaders in the world, we need a culture change. As long as sexism persists our law will fail to serve women and our people will fail to respect them. The good news is culture changes everyday. If we can bring drop-crotch pants into fashion, then surely we can bring equality into fashion,” she says.


How She Lets It Go: Stop Grading Yourself

Jen Lee Koss, cofounder of e-commerce site Brika

Photo courtesy of Brika

“As a mother of two young children and running a startup, my life can feel totally upside down and inside out most of the time. Sometimes I wonder if what I’m doing as a startup founder and as a mother is ‘enough.’ It used to eat me up inside, but then I realized that it was debilitating to imagine being an ‘A’ at both,” says Koss.


“I’ve stopped grading myself and have focused on the hustle. It’s about being able to get things done and to demonstrate little wins each and every single day–whether it’s an email response I wanted from someone we’re trying to partner with or getting my kids to eat a handful of carrots, I’ll take it,” she says.


About the author

Vivian Giang is a business writer of gender conversations, leadership, entrepreneurship, workplace psychology, and whatever else she finds interesting related to work and play. You can find her on Twitter at @vivian_giang.