Failure to Launch

Fear of failure holds many of us back. But if we heed the Silicon Valley motto— “Fail Fast, Fail Often”—­we may be better able to achieve our goals and advance our careers.

By Ellen Lee

Accelerate_Art_ThumbSteve Jobs was the ultimate failure. He dropped out of college, he was ousted by the company he cofounded, and the computer he designed was panned by the media. Yet today Jobs is remembered as one of the most iconic and revered figures in technology.

Can we benefit from failure? In Silicon Valley, where the motto “Fail Fast, Fail Often” rules, the answer is a resounding yes. Design a product that didn’t work? Go back to the drawing board and try again. Failure, the thinking goes, is just one step on the road to the right solution.

That approach could benefit many of us in all facets of our lives. Women often feel the pressure to be perfect—perfect looks, perfect job, perfect mom. Social media, and the trend toward sharing the most important events in our lives, hasn’t helped.

Indeed, we ahave good reason to feel the pressure to be perfect. Women, more so than men, are highly scrutinized in their climb up the corporate ladder, especially because so few of us have made it to the top, according to a 2013 paper in the Harvard Business Review. Women of color face additional challenges. Research shows, for example, that when black women are seen as not fitting the “mold” of a leader, they are punished more harshly than their black or white male counterparts if they make a mistake. Is it any wonder that we are cautious about blundering?

At the same time, if we were to borrow from the Silicon Valley school of thinking, the potential for failure shouldn’t stop us. In fact, despite the risks, we should run headlong into it.

Part of the process

The root of Silicon Valley’s “Fail Fast, Fail Often” motto is the technology industry’s need to innovate quickly and stay competitive. (The many incarnations of the iPhone are just one example.) The strategy goes something like this: Design a prototype. Instead of making sure it is absolutely perfect, test it—ideas aren’t meant to stay on the proverbial whiteboard. Solicit feedback and figure out how the prototype can be tweaked and improved. Then try again. And again and again and again. That same mind-set describes the industry’s entrepreneurs. Silicon Valley is littered with people who have started an endeavor, failed, and moved on to their second, third, or even fourth one. They aren’t expected to be Mark Zuckerberg and launch Facebook on their first try (incidentally, for many years, Facebook’s internal motto was “Move Fast and Break Things”).

How can we learn from Silicon Valley? We need to accept that making mistakes is part of every aspect of life. “Our challenges are going to involve failure because if it were easy, it would have already been done,” says Ashley Good, founder of Fail Forward, a Toronto-based consultancy that helps organizations and individuals learn from their failures.

One of Silicon Valley’s popular buzzwords is to iterate. The concept is the same: figure out what went wrong and what went right and build on it. It means drafting a proposal and then revising it again and again, rather than being held hostage by the need to craft the perfect introduction. It means experimenting with different tactics if the first one doesn’t work out. It means taking risks.

And it means not fearing failure. A study at Smith College asked 51 female undergraduates to rewrite a passage from a composition. Their assignment was then blind graded by two college professors. The study found that the students who were considered perfectionists did a poorer job than those who weren’t. Randy O. Smith, the psychology professor who conducted the study, theorized that perfectionists avoided showing their writing to others and having it critiqued, so they didn’t receive the feedback that could help them improve. They feared getting it wrong, yet it was their fear of failure that hindered them in the end.

“You have to be ready to make mistakes and try again,” says Alina Tugend, author of Better by Mistake: The Unexpected Benefits of Being Wrong, which cites the study. “It’s something we lose sight of.”

Sometimes it’s harder for us if we grew up with a string of successes, Tugend adds. We’re used to striving for the best and being the best, so when we hit a roadblock, we’re not equipped to handle it.

That happened to Mari Corella. “I had been an overachiever my whole life,” Corella explains. “I believed that if you worked hard, you would get a good job and life would be good after that.”

After graduating from University of California at Berkeley, Corella landed a position at a national fashion retailer. A year in, she applied for a promotion, confident that she would be selected. She wasn’t. The decision wrecked her. She searched for answers. Was it something she had done? Was it because of her background (Latina and Asian)? What did she lack? She felt so miserable that her unhappiness began to manifest itself in aches and pains in her body. She snapped at her colleagues at work. She cried. She was mean to new hires. “I became a disgruntled employee,” she says. “I did many things I was not supposed to do.”

Corella spent a year interviewing for other jobs, but the economy had stalled and she couldn’t land a new position. Finally, she applied for business school, was accepted, and earned an MBA. The move helped restart her career. “Failure is a gift, a clear sign to try a new method of achieving your goals,” says Corella, who is now a digital executive at a national beauty company in New York.

Early on, Corella put too much pressure on herself. She’s since learned to shake off failures, and she’s also more compassionate with those around her when they make mistakes. “We can’t change what’s happened to us in the past,” she says. “We can’t change what’s going to happen in the future. But we can change how we react to both.”

Failing forward

Most of us don’t handle failure well, says Good of Fail Forward. We want to blame others or point to extenuating circumstances. But we can learn to “fail forward.” The first step is to recognize the instinct to find fault elsewhere and move beyond it. Instead, it’s important to reflect on the situation and to ask ourselves what or how we can change—and grow. What can we do differently next time? After all, we don’t want to make the same errors again and again.

It also helps to have a trusted friend or mentor with whom you can share your story. Our impulse may be to hide our mistakes, but being open about them can help. “We are often harder on ourselves, so the act of sharing brings us out of the death spiral of despair,” says Good.

“This is not a nice-to-have skill,” she adds. “It is a must-have skill because of the complexity of problems we’re trying to solve. Everyone is going to need a productive relationship with failure.”

Jessica Bacal, author of Mistakes I Made at Work, stresses the importance of self-compassion. Our mistakes don’t have to define us. That is, just because you lose doesn’t mean you’re a loser, and just because you fail doesn’t mean you’re a failure. “One thing you’ve done doesn’t represent your whole self and your whole career,” she says. “It’s useful to give yourself the compassion that you would offer to a good friend.”

Bacal was inspired to pen Mistakes I Made at Work after she was named director of the Wurtele Center for Work & Life at Smith College. Faced with a steep learning curve, she found herself feeling anxious about the mistakes she kept making. In her book, she turned to 25 prominent women, such as author Cheryl Strayed and McKinsey director Joanna Barsh, and asked them to share a mistake they had made and how they overcame it.

Reshma Saujani was one of the women Bacal featured. Saujani had run for Congress in New York and had lost in a landslide. She gave herself two weeks to feel terrible, then picked up the pieces and eventually took a public advocacy job. In her new role, she found that students, especially girls, in New York City public schools did not have enough access to technology education. It inspired her to start the nonprofit Girls Who Code. The training program now reaches nearly 4,000 girls in 29 states, with the goal of exposing 1 million girls to computer science by 2020. Failure gave Saujani the power to take more risks because she felt like the worst had already happened.

“Failure can make you stronger, tougher, and more resilient if you look at it the right way,” she says. “Girls Who Code might never have been founded if I had won [the election].”

Failure opened the door for Tiffany Gillespie, too. A few years ago, Gillespie felt that she had landed her dream job when she was hired by an event-planning company. But three months into it, she forgot to place an order for a client. The mistake cost Gillespie her position. “I was devastated,” she says. “I had never been let go from a job. I felt like such a failure.”

Gillespie, who had studied criminal justice in school, returned to the legal industry and took a temporary job at a law firm. But she still loved event planning and continued to pursue it on the side. When her law firm gig ended, she decided not to search for a new position. Instead, she launched To the “T” Events and Catering in Philadelphia. She gave herself six months to make it work. It did. Now more than a year later, she is organizing weddings, book tours, and corporate events.

Although Gillespie still regrets that fateful mistake, she might not otherwise have had the courage to go out and launch her own business. As she says, “That mistake was the best thing that happened to me.” DW

Ellen Lee is a business and technology journalist in the San Francisco Bay Area.


It’s important to reflect on the situation and to ask ourselves what or how we can change—and grow.

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