Course 3: Learn How To Lose


“A writer – and, I believe, generally all persons – must think that whatever happens to him or her is a resource. All things have been given to us for a purpose, and an artist must feel this more intensely. All that happens to us, including our humiliations, our misfortunes, our embarrassments, all is given to us as raw material, as clay, so that we may shape our art.” Jorge Luis Borges

Humiliation, misfortune, embarrassment – none of these are the personal experiences we hear leaders talk about very often.  Leaders are supposed to be the strongest of the strong, the surest of the sure – staring down life’s tempests, and winning!  They have forged their path with confidence and self-assuredness.

For education to meet the tremendous opportunities and challenges of the 21st Century, our silence on these matters must end immediately!

Leadership School 2.0 offers a different perspective on how leaders earn their stripes in building the credibility, expertise, and mindset to move their organizations forward.  They don’t do it by winning; they do it by losing.

The words of the incomparable author Jorge Luis Borges provide the key question: What well do we draw from to “shape our art?”  What makes us stronger, more resilient, more adaptive, more self-reflective, more thick-skinned?  In short: What makes us better?

That’s right: losing does.

I believe it is important that we take a broad view of “losing” to ensure we go beyond the realm of competition, where losing is very easy to define: two sides come together – one side wins, the other side doesn’t.  This is not to say that the sporting world doesn’t offer a valuable analogy to leadership growth – think about the oft-told stories of athletes cut from their high school teams who have become some of the greatest players ever in their sport.  What well did they draw from to get stronger, more resilient, more adaptive?  Yep – losing.

Or how about the endurance athlete who trains for months in preparation for a big event, only to drop out on the big day due to cramping?  Not a “loss” technically, but certainly a failure to accomplish the fundamental goal of finishing.  When she goes back to the drawing board (trust me – she will!), she will analyze everything contributing to her performance and will implement those findings her next time out.  Loss = growth.

Enough about sports; what do the Arts have to teach us?  Consider the thespian who rehearses for months, performs a stellar audition…and doesn’t get the role.  The writer whose manuscript is rejected time and again.  If leadership is an art (I propose that it is), then it is time for us to mirror the artists and athletes who are constantly responding to feedback on their work – and who can very clearly see how they are falling short and what they need to do to to meet and exceed the benchmarks they have set for themselves.  In the case of Mrs. LeGuin’s rejection letter, it might simply be the persistence to seek out another publishing house.  For someone else, the next step might be a rewrite.  “Loss” can be the first step to making something great.

This sounds a lot like what we want to see in our students – the 21st Century skill set that will make them the creators, innovators, collaborators, and communicators of the future.  Is it any surprise that perseverance is a critical skill embedded in the Common Core?

There are many types of loss we will encounter in our work as leaders: loss of valued colleagues (and friends) to other jobs; loss of old, familiar ways of doing things (textbooks, anyone?); loss of beloved programs due to staffing, budgetary, or structural changes; the unthinkable loss of life of a student or staff member.  What is our emotional preparedness?  How do we handle our disappointment, frustration, or grief before we even begin to consider that of our organization?

We will also experience personal setbacks in our leadership journey: not getting a sought after promotion; being released from a leadership position; bringing a great idea forward that doesn’t take root.  Do these setbacks move us to silence, or do we continue seeking – water finding its way to the ocean?

Our organization will look to us for leadership in technical, structural, interpersonal, and emotional realms.  This is by no means “fair” – yet it is the earthly weight we must bear, our inner Sisyphus toiling up the hill.  By learning how to lose – and modeling the adaptive resilience we want to inculcate in our students – we continue to build our credibility with others and, even more importantly, our own sense of confidence and purpose.

Guiding questions for Course 3:

1) What time and space do you provide yourself – and your school – to process and grieve loss?

2) What support network do you have for yourself in confronting the inevitable losses you will face?

3) How can you share your experiences with loss transparently to help others build their own confidence and willingness to take risks?

4) How do you cultivate resilience?

5) What place does learning from failure have in your school culture?

Image of Sisyphus (Titian, 1548-49) courtesy of Museo del Prado.

One thought on “Course 3: Learn How To Lose

  1. Just a quick note before reading this post: The visuals on your posts are a photo essay in and of themselves! This one got a laugh out of me, a disgruntled laugh, I guess, after our conversation from last night.

    Write On!

    xoxoxo Mom

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