Failing Fast and Succeeding: How Smart Women Build Confidence

Article by Wendy Sachs

Big trends have a way of touching all of us. From tattoos to Birkenstocks to gay marriage, certain ideas, products, and political movements are able to reach critical mass and gain acceptance, folding into the fabric of our collective culture. Today, Silicon Valley and the startup world are our cultural crushes.

Our love of the Valley is part mythology, with its "unicorn" billion-dollar startups like Uber and Airbnb, and part psychology, with its change-the-world, disrupt-the-status-quo, always-innovating ethos. In the past decade, Silicon Valley has become our North Star, influencing everything from news and entertainment to public policy and workplace culture.

The celebrated startup model of disruption that embraces failing fast and pivoting is not a typically female one. Women tend to be more risk averse. We can overthink our next move and not act until we're 100 percent ready. We might feel like frauds when we're trying something new. Instead of being disruptive, women tend to be more disciplined. We're often not pivoting because we're stuck.

So, what would happen if women were to embrace the startup model? What if we had the confidence to take risks knowing that we might fail at first? What if instead of agonizing about which step to take, we leapt forward quickly? What if we could apply the lessons of iteration, engineering serendipity, failing fast, networking, and strategic branding to help us redirect our paths, enhance ourselves, or transform our careers?

The Failure Fetish

Embracing failure has become fetishized in Silicon Valley. With an estimated 9 out of 10 startups flaming out within a few years, failure is as universal in the Valley as relentless optimism. Believing that they are working on the next big thing that will transform the world keeps those in the startup space grinding away, even if the staggering odds of success are against them. This is the beauty of the culture of innovation: An environment that encourages risk ultimately creates change.

Failure wasn't always so fashionable. The tech world used to bury its dead without much fanfare. Companies folded quietly. Founders whose businesses flopped were rescued and hired by friends. But then something changed. In 2009, Cassandra Phillipps, an event production planner who had entered the startup scene in San Francisco, grew tired of pretending that everything was perfect with her social media business. She launched FailCon, an event where entrepreneurs could share their stories of epic fails, the lessons they learned, and the emotional roller coasters they experienced. This was Phillipps's way of making it real, ripping the facade off of the founder's myth that everything was fabulous.

Phillipps felt that wherever she went, people would boast about their successes and talk about how great things were going and how pleased their investors were with their company's growth. But that wasn't Phillipps's experience. Her company was floundering. She was depressed. She longed for support.

"I would go to the events and everyone was so positive, and I felt like I had to do the same thing or I would be kicked out of the community," Phillipps says. "It felt like you were a failure if you were having problems. You couldn't ever be honest about how you were doing. It made me feel like personally I was a failure. I wondered why everyone around me was doing so well. I felt like we couldn't discuss it in this environment."

So Phillipps changed the environment. The FailCon event was a safe space to share what went wrong. When it launched in 2009, it was a huge success, with nearly 500 people at the inaugural event. It quickly grew to more than 20 events around the world. Now, the once-quiet funerals of startups have loud platforms where people can publicly mourn and broadcast their experiences. It has become trendy for entrepreneurs to post their postmortems on blogging platforms such as Medium. Some even see it as strategic a strategic move: announcing their failure could be a way to look for another job. It's like advertising: "Hey, I did all of this great stuff, but it didn't work out. I'm seasoned, I failed, hire me!"

The "fail fast" mantra is popular in the tech industry, where many products aren't fully baked before prototypes are released to the public. Think Gmail, which was released internally to Google employees in the early 2000s and released to the public a few years later in 2007. Such unfinished products are known as "beta" versions.

The tech world is obsessed with speed and getting to market first. The expectation is that nothing you initially launch will be perfect, and it doesn't need to be. It's not about perfection; it's about acting quickly. Companies try out products for people to test. They keep what sticks and toss what doesn't. It's a learning experience: They improve features, they tweak, they iterate, they adjust, just so.

Failing Fast Builds Confidence

This model of risk, act, fail, and iterate is equally useful in our careers. Many psychologists say failure is a valuable step in the journey to success. It's a critical learning tool, because it forces you to dig into your reservoir of grit. It tests your perseverance and can ultimately make you stronger.

"Failure really can be an asset if we are trying to improve, learn or do something new. It's the feature that precedes nearly all successes. There's nothing shameful about being wrong, about changing course. Each time it happens, we have new options. Problems become opportunities," writes Ryan Holiday, author of The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph.

Talk to anyone in the midst of failure, and they'll say it's messy and awful. There is plenty of pushback now about how glorifying failure masks the horrible reality of the toll a tanking company takes on its founders. But for women, there is something to be learned from the startup culture that takes the stigma out of failing and encourages risk: confidence.

The proven way to gain confidence is to take action. Even in failure, you've acted. You've taken risks. You've learned. And out of failure comes growth.

"We've come to see the theory of failing fast as the ideal paradigm for building female confidence," write Katty Kay and Claire Shipman in The Confidence Code. "If we can embrace failure as forward progress, then we can spend time on the other critical confidence skill: mastery."

Mastery, of course, comes after getting really good at something. The more time you put in, the more adept you feel and the more confident you become. Taking action is the first step toward becoming confident.

And if at first you fail, well, know that you're in good company and success is around the corner.

A version of this article previously appeared on

Adapted from Fearless and Free: How Smart Women Pivot – and Relaunch Their Careers by Wendy Sachs. All rights reserved. Published by AMACOM Books.

Wendy Sachs is a master of the career pivot. An Emmy-award winning TV news producer, Wendy has worked at Dateline NBC, Fox, and CNN. She also worked as a Capitol Hill press secretary, public relations executive, CNN contributor, content strategist, and editor-in-chief of In a more random role, Wendy appeared as the on-air spokesperson for TripAdvisor. A frequent speaker, Wendy has written about work/life and women's issues for multiple publications, including The New York Times,, the Huffington Post, and Refinery29. She has appeared on dozens of radio and TV shows, including Good Morning America, NBC's Today, Fox, and CNN's Headline News. Wendy lives with her husband and two children in South Orange, New Jersey. For more information, please visit and follow the author on Facebook and Twitter.