Fail Gloriously, Lead Well*
Mariandl Hufford

One of the highlights of my year has been meeting with a group of upper school girls (recipients of the inaugural Moulton Grant) on fleshing out their idea for creating a middle school leadership program that is developmentally suited to this older age group.

The girls’ commitment has been commendable — they never miss our weekly meetings — and their energy, creativity, and enthusiasm have fueled my own. There are other adults in the room, too, and together, we are slowly but surely driving toward our goal. The girls’ ideas are taking shape, and with the input of students and teachers in our middle school, will surely impact their younger sisters’ leadership identity.

In our earliest conversations, we talked about what we know about girls in middle school, and their possibly reluctant stance toward claiming their leadership voice. We talked about the awkwardness that is so often a part of those middle years. We discussed how girls can worry about being seen as bossy by their peers, or about losing friends when a decision is unpopular.

We also talked about the fact that running for elected office (one form of leadership) is a highly vulnerable endeavor that opens oneself up to the sting of failure. We talked about how failure is an inherent part of stepping into a space that, because we are not clairvoyant, is unknown and unknowable to us. And we talked about how for girls, in particular, that risk of failure is a very hard concept to embrace. The pressure placed on girls to be “practically perfect in every way,” as Mary Poppins so famously said, has been discussed in a variety of outlets and I will not detail it here. It is important to note, however, that this pressure can make girls risk-averse, which, we know, will, in turn, rob them of the opportunity to discover in themselves what they are truly capable of. Brene Brown speaks eloquently about how vulnerability is “our greatest measure of courage,” and each of us, in girls’ schools, hopes just that for our students — the uncovering of courage to risk, fail, and try again.

I pointed out to my group of intrepid upper school girls that I once read about a girls’ school in the UK that celebrated “failure week” in order to help its students become comfortable with the idea of failing for all of the reasons I listed above. One girl, smart, bold, insightful, and honest, grabbed the arms of the chair in which she was seated. She sat up straight, caught her breath, and exclaimed: “I think we are going to have to incorporate something like that. The thought of it alone makes me anxious — I guess I really need it.” We all chuckled — because of her disarming honesty, but also because we could all relate. Failure can be excruciating; the (temporary) loss of confidence alone is enough to make us shrink back to doing what is safe and predictable. But here is the irony: the more we risk and the greater the potential for failure, the harder it becomes to retreat, permanently, to safe ground. Good leaders know this; once you have imagined greater possibilities for yourself and others, it is hard to remain satisfied with the status quo.

And because we have seen what is possible, we dust ourselves off and reach for the next opportunity to make our vision reality.

At one of the more recent planning meetings we held as a group, this same girl and a collaborator proposed that we create our own version of the Game of Life for our middle schoolers to play in which risk and decision making will inevitably lead to moments of failure, but also moments of triumph. The point of the game: becoming comfortable with the fact that life is not just smooth sailing, and that to grow, and to lead, we need to make ourselves vulnerable and take bold risks that may, indeed, lead to failing gloriously.

*The first part of title of this blog “fail gloriously,” is attributed to actress Cate Blanchett, who said: “If you know you are going to fail, then fail gloriously.”

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