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No More Playing It Safe: Why Female Entrepreneurs Need to Take More Risks

By Business.com Editorial Staff
Business.com / Entrepreneurship / Last Modified: February 22, 2017

To be truly disruptive, you need to purposely shake your personal status quo. Women in particular need to find the confidence to take risks.

In school, you got detention for being disruptive. Today, it’s what companies strive to do—for all the advances in gender equality, should women business leaders still face a male-dominated status quo in the corporate boardroom and the entrepreneurial startup community?

What does it really mean for a company to be “disruptive?" A term favored in press releases and industry media coverage, it basically means doing something different, challenging pre-conceptions and breaking out of conventionally accepted operational models.

Mike Myatt of N2Growth notes that disruptive companies offer distinctive competitive value. "Me Too" companies fight to gain market share in an attempt to survive, while disruptive companies become category dominant brands.

Myatt goes on to point out that the reason why many well-established companies struggle with becoming more disruptive is the difficulty in breaking old habits. They have been, he says, “doing the same things, in the same ways, and for the same reasons for so long, they struggle with the concept of change.”

Breakthrough Confidence 

We all struggle with change. For business women, the struggle isn’t just breaking out of their personal status quo, it’s also breaking through the norms of a workplace that still harbors gender stereotypes. The reason why we still talk about a glass ceiling is because it still hasn’t been shattered.

How do women business leaders gain the confidence to be more disruptive? By taking risks that build on female strengths and correct weaknesses—perceived or otherwise—about how they stack up to their male colleagues. As Melissa Woo, CIO and vice provost for information services at the University of Oregon notes,

“Not only am I a woman in IT, but I’m very petite and I dress like a woman, in a dress or skirt—I don’t look like a tech person. People think I’m not tech savvy. A lot of women in IT have to spend more effort in proving themselves than a man with equivalent skills and experience.” 

Was That a Joke?

Careers in comedy are notoriously tough. Audiences, particularly young ones, recoil from the politically correct departures necessary for comedy's social critique, reports "The Atlantic." Breakout stars like Sarah Silverman, Chelsea Handler, and Amy Schumer have made careers by being willing to take great risks. With it comes negative pushback.

Caitlyn Flanagan writes, "Sarah Silverman has described the laugh that comes with a “mouth full of blood”—the hearty laugh from the person who understands your joke not as a critique of some vile notion but as an endorsement of it."

Award-winning comedian Mindy Kaling can relate. She shares her recipe for building confidence to take on more risk to "Glamour" magazine. It comes from her book, "Why Not Me?":  

"Work hard, know your shit, show your shit, and then feel entitled."

Related Article: Ladies Take the Wheel: How Women are Driving Business Innovation

The Damage From Risk Aversion

Women generally are more collaborative. Deanna Oppenheimer, global consultant and former CEO at Barclays Bank in the UK, says this is a way for women to prove themselves in today’s workplace, and particularly in the IT field. “Technology is advancing every day and causing new disruptive forces in virtually every industry. In times of the unknown, you need a lot of different perspectives in trying to chose a strategy, a direction, rather than a top-down approach by one person who knows it all.” 

But as Sharon John, president and CEO of Build-a-Bear Workshop, notes, “Certain talents come naturally, but you can’t use your innate abilities as an excuse not to master inadequacies…You need to play to your strengths, but not ignore your weaknesses, and you have have to be brave to do both.”

As Julie Zellinger points out, one such weakness is that women aren’t generally known for taking risks. Indeed, there have been suggestions that the economic meltdown of 2007/2008 might not have occurred if more risk-averse women were in more prominent positions of power in the financial world. 

While that would certainly have been a good thing, in general women’s tendencies to avoid risks, to be less disruptive, is damaging to their careers. As Pamela Barnes, CEO and president of EngenderHealth, puts it, ”For all professionals, and especially young women, the world outside our comfort zone can be huge and scary. Until we are willing to put ourselves out there and take a risk, we will never able to achieve professional success and realize out potential.”

Related Article: Lessons from Lynn Tilton, the Wonder Woman of Wall Street 

Disrupting Gender Stereotypes

Here are the benefits to women of taking more professional risks and disrupting gender stereotypes:

  • You can learn something. Besides a broader skills portfolio that may make you that much of a better candidate for your next career move, you might learn something invaluable about yourself that you never realized. That might give you even more confidence to take the next risky move.

  • It creates a higher standard. Here’s where the typical males sports analogy is especially relevant. Every time someone sets a new record in any competitive sport, it becomes the benchmark to not only equal, but surpass. When you take risks that show how much you can attain, it inspires others to follow your lead. Otherwise, you’re just running in place with everyone else.

  • It overcomes the fear of failure. Again, it’s a generalization that often holds true—women tend to have a greater fear of failure. Yet failure is what helps you learn what doesn’t work and do better the next attempt. How to overcome a fear of failure? Keep risking the possibility. Once your failures eventually lead to success, you might even start to embrace failure. Arianna Huffington told CNN that she experienced multiple failures, including a book that was rejected 36 times. This is the woman who has made the most powerful people lists of both "Time" and "Forbes" and sold her "Huffington Post" (which she still runs) for $315 million.

  • It gets you noticed. Nothing ventured, nothing gained. At the very least, a willingness to take a chance (as long as the chance is not reckless or otherwise destructive) is something people take notice of. No one really notices the people who are just content to get their time cards punched because that’s all they’re doing.

Perhaps not taking a risk is the one risk you can’t really afford to take.


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