Skillsoft Blog

Failing Fast and Succeeding

Wendy Sachs

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 have an uncanny ability to reach critical mass and then gain acceptance, folding into the fabric of our collective culture. Today, Silicon Valley and the start-up world are our cultural crushes. It’s part mythology with its unicorns, the billion, dollar start-ups 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 start-up 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 may feel like frauds when we’re trying something new. Instead of being disruptive, women tend to be more disciplined. And we’re often not pivoting—because we’re stuck.

So what if women embraced the start-up model? What if we had the confidence to take risks, even if we knew we might fail first? What if instead of agonizing about which step to take, we leapt forward quickly? What if we could apply lessons of iteration, engineering serendipity, failing fast, networking, and strategic branding to help us redirect our path, enhance ourselves, or transform our careers?

The Failure Fetish

Embracing failure is an idea that has become fetishized in Silicon Valley. With an estimated nine out of ten start-ups flaming out within a few years, failure is as universal to the Valley experience as relentless optimism. Believing that they are working on the next big thing that will transform the world keeps those in the start-up space grinding away, even if the staggering odds of success are against them. But that 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 got rescued and hired by friends. But then something changed. In 2009, Cassandra Phillipps, an event production planner who had entered the start-up scene in San Francisco, grew tired of pretending that everything with her social media business was perfect. She launched FailCon, an event where entrepreneurs could share their stories of epic fails, the lessons they learned, and the emotional roller coaster they experienced. This was Cassandra’s way of making it real—ripping off the façade of the founder myth that everything was fabulous.

Cassandra had 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 Cassandra’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,” Cassandra 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 she 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 five hundred people at the inaugural event. It quickly grew to more than twenty events around the world. Now the once-quiet funerals of start-ups have loud platforms where people can publicly mourn and broadcast their experiences. It became trendy for entrepreneurs to post their postmortems on blogging platforms like Medium with essays like “First Start-Up. First Flop.” Some even saw it as strategic, announcing their failure as 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!”

Aside from owning failure as a professional bragging right, the “fail fast” mantra is often cited as a popular business technique of the tech industry. The idea is that many products aren’t fully baked before prototypes are released to the public. Think Gmail: It was released internally to Google employees in 2007 and then released to the public a few years later. These are known as the beta versions. The tech world is obsessed with speed and getting first to market. The expectation is that nothing you initially launch is perfect—it doesn’t need to be. It’s not about perfection; it’s about acting quickly. Companies try out products for people to test. What sticks they keep, what doesn’t they toss. It’s a learning experience. They improve on features, they tweak, they iterate, they adjust, just so.

Failing Fast Builds Confidence – This model—risk, act, fail, and iterate—is equally useful to our careers.

Many psychologists will point to experiencing failure as a valuable step in the journey to success. It’s a critical learning tool because it forces you to dig into your own reservoir of grit. It tests your perseverance and ultimately can 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.5

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 start-up 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 Kitty 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 ultimately, the more confident you become. So taking action is the first step to becoming confident. And if at first you fail, well, know that you’re in good company and success is around the corner.

Fearless and Free - Wendy Sachs book

Join us on, March 22 for Skillsoft Off the Shelf Book Club Webinar: Fearless and Free: How Smart Women Pivot and Relaunch Their Careers


This webinar is part of Skillsoft Off the Shelf, a virtual book club for modern learners. Watch the launch video interview with the author and get access to the book resources offered on the Skillsoft platform, Percipio.


Wendy Sachs is a modern multi-hyphenate. A passionate storyteller, she is an Emmy award-winning network television producer, former Capitol Hill press secretary, editor-in-chief of, media relations executive, content strategist and the author of the critically acclaimed Fearless and Free: How Smart Women Pivot and Relaunch their Careers. Wendy has been recognized by MAKERS and was also named in 2017 on as a “40 Over 40 Woman to Watch.”

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