Real Talk about Failure

Last week, a group of strangers and I sat around a room talking about times we had failed. No, this wasn’t a group therapy session. It was part of the Vox “unconference” I attended, where attendees lead discussion groups on a variety of topics.

I had four other options to attend that session (e.g.: "How Can We Fix Healthcare"; "Making the Gig Economy Work for You") but I was drawn to the failure discussion. I chose the topic because I think a lot about what it means to admit to the world that you have failed and yet somehow go on anyway. This is one of the most difficult things we humans are called upon to do. And so I joined the group in sharing what I consider my biggest failing.

I have experienced plenty of failure in my life, most notably losing a big job in my early 30s and losing my marriage in my 40s. Although one of these was professional and the other personal, they both had the same three elements: I lost something that I wanted to keep, my whole extended community knew what had happened, and I had to reinvent myself and change my course in order to survive. I am a big believer that failures make you a stronger and better person, as long as you take the time to really examine what went wrong and you use that information to create a better path forward.

At the conference, however, I didn’t talk about either of these life-altering events. Instead, I spoke about something much more personal. I shared that although I spend my life talking to young women about confidence and leadership, I frequently second guess my own leadership skills and worry about whether I am good enough at what I do. But as the leader of an organization, isn’t it my job to be the most self-confident and invulnerable person I can be?

As president of Running Start, an organization that helps bring young women into politics, I know that women are much more likely than men to report feeling unqualified for top jobs, insecure about whether they deserve a seat at the table, and lacking in confidence that they have what it takes to lead. There are many reasons that women feel less sure about their leadership abilities than men, including, of course, that for most of the history of the world, leadership was not our job and we are in many ways still creating what it means to be a female leader.

My message to these young women is that although you may occasionally doubt your qualifications, you need to work on quieting that voice in your head and pushing through, because you are inevitably better than you think you are. Claire Shipman and Katty Kay talk about this in "The Confidence Code." Women are wired so that we doubt ourselves more than men, but this doesn’t have to hold us back. As the book says, our brains are very plastic, and we can train ourselves to look and feel more confident. I know (because I’ve done it) that it’s possible to feel scared and insecure but to walk onto a stage and look like you rule the world. A big part of any leadership has got to be the ability to bluff.

But when does that bluffing create obstacles for other women? Twice last week, I had women tell me that they didn’t understand why building confidence was a part of Running Start’s training. They both said versions of the same thing: I feel confident in my abilities and I’ve never doubted that I was as qualified as the people around me. Both were at the top of their professional games, but I would hesitate to make them mentors for the young women I train. My favorite role models are those who say “Yes, leadership is hard, and yes, I struggle, but it is worth it and you can do it.”

Few of us are 100 percent confident in ourselves. Some of us learn to push on and do the job well even if we aren’t always sure we can, and others use lack of confidence as an excuse not to step up and do hard things. It’s clear that pushing through insecurity is the way to go, but letting others see a bit of this struggle is important too.

A young woman came up to me after the conference to say how much it meant that I shared my story of self-doubt. She said that knowing I feel this way makes it seem possible for her to succeed too. Which made me realize that lacking confidence isn’t my real failing: It is not being brave enough to admit that I feel this way.