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This CEO allows herself 5 fails a day: 'It gives you a competitive advantage'—here's why

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Caroline Wanga at the 2023 TIME Women of the Year Gala held at the Four Seasons Los Angeles at Beverly Hills on March 8, 2023 in Los Angeles, California.
Gilbert Flores | Variety | Getty Images

The secret to success could lie in your failures.

Caroline Wanga, the president and CEO of Essence Ventures LLC, says she came to the startling realization in her 30s after "being held captive by failure" for nearly 20 years.

At that point in her career, Wanga had achieved a feat most people could only dream of, becoming a C-suite executive at a multibillion-dollar company, when she was appointed Target's chief diversity and inclusion officer in 2014.

Yet as Wanga, 45, recalls, she spent much of her free time in between meetings checking the social media profiles of girls she went to high school with, comparing their lives to hers and fretting that they had "better, cooler" jobs. 

In her mind, Wanga was still 17, the age at which she got pregnant and dropped out of college to raise her daughter Cadence. "I was still stuck at the point that I had my daughter, and so all of the things that I had accomplished since then, I had no idea what they looked like," says Wanga. "I could only ruminate on the things I had failed at, which had become debilitating."

Once Wanga paid closer attention to how she was defining and handling setbacks at work, she discovered that overcoming your fear of making mistakes and bouncing back from a failure are two of the greatest strengths you can have. 

Here is the "super simple" hack she uses to recover from failure.

Allow yourself five fails a day

To quiet what she calls her "inner saboteur," Wanga created a high threshold for failure: She gives herself five fails a day. It's only if she reaches a sixth fail that she considers it a bad day. 

"That number felt unattainable, almost like a challenge to myself," she says. By giving herself the freedom to fail, Wanga has increased her risk tolerance and become more resilient when things go wrong.

"It's normal to be pissed when a failure happens, but the issue is, how are you ascribing that failure to your whole day, or life, instead of just letting it be?" says Wanga. "I gave myself permission to be as pissed off as I wanted to be any time a failure happened, but what I don't get to do is say it's a bad day until I hit six, which reduced the power failure had over me." 

Wanga recommends setting a threshold of fails that you're comfortable with — it can be five, but as she stresses, there are no "magic numbers" in failing —  and sticking to it, no matter how frustrated you get making mistakes at work. 

How to turn failure into a competitive advantage

Learning to bounce back fast after failure can be one of the hardest skills to master, but one of the most valuable assets you can have in your career, says Wanga. 

"You might be on a call with me at 9 a.m. where I'm livid about something, and then you get on another call with me at 3 p.m. and I'm just fine, because I know I have one, two or three fails left in the day," Wanga explains. "Unless it's the sixth fail, I don't need to dwell on it, and if it is, I have a longer check-in with myself after work."

That mindset gives you a "competitive advantage" at work because "it might take someone at least 30 minutes to recover from an upsetting thing that happened, but you'll be good after five," she adds.

Even though failure is an important part of success, Wanga says she's surprised at how few business leaders will openly talk about the setbacks and challenges they've faced.

"Most people like to share stories in perfection, the way they'd want it to be told in a made-for-TV inspirational movie," says Wanga. "But the problem with that is that everyone f---s up on a daily basis, at least several times a day."

She continues: "If you tell a story about your achievements, and there's no mention of anything going wrong, people that aren't perfect won't think success is attainable for them. I wish more leaders were transparent about the ways that they've failed. Talk about the triumphs, but also the trials, because the truth is, there are always bumps in the road to success."

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