On Teaching Failure: Words from a Winterline Field Advisor

By: Nick Manning | June 28, 2019
Topics: Uncategorized
"One of the hardest things to teach others is failure because we inherently and culturally want to avoid it." - Nick Manning, former Field Advisor and current President for the Winterline Gap Year Program

This came up for me some time ago as I sat on the edge of a bed with a dear friend. Her baby and my niece, 7-month old Sylvie, lay several feet away snoring as though the world were her protector and that bed were a cocoon of safety and light. I told Jenny that I constantly found myself in situations that push me beyond what I am comfortable with. It is not a conscious decision, but one rooted in some deep part of my internal landscape where growth and the desire to become fully awake and fully open in heart and mind are a driving force beyond my navigation skills. I crave comfort and stability, yet I embark upon a life of instability and sped up change

winterline, gap year, teaching

When I reflect on why I constantly find myself in front of young people in tough places, acting as a self-declared mentor of sorts, I can’t help but ruminate on why I choose to take on such a bold task given how my life has unfolded thus so far. I find thoughts running through my head that there has to be someone more adjusted and better suited to such a monumental task. What I’m learning is that there is a massive thread of intention that guides me forward and across the paths of these young people. And it is that intention that is needed, not the illusion or allure of precise measurement or perfection.

There’s something enthralling about offering up a lifetime of experiences to someone who is still on the threshold of figuring out who they are and how they fit into the world around them.

That gift does not mean I have to have expertly figured out how to live, it simply means I am present and aware. The word “guide” has always felt more appropriate than teacher – the intersection of the monastic life and that of a teacher within one degree of separation upon a large sundial of how I fit within society.

Why work so hard on self, on increasing the quality of life for myself and those around me? There is this funny little f-word (no, not that one!) that has taught me more about being human and doing right in this world than any textbook or piece of quixotic internet advice ever has – failure.

winterline, gap year, teaching

I stand in front of young people in the hopes of modeling the sort of behaviors and actions it has taken years of hard work to get to. I stand in front of youth because I envision a world where the practices, programs, and relationships that have created the best of being human within all of us, are part of our upbringing and part of the rhythm of our communal growing-up.

But then I come back to the f-word and I hesitate to create a world where all the answers are perfect and all the people are pure and wise. Somewhere I know this to be true, but it is the path forward, often laced with f-word breathing dragons that makes us whole and full of grit.

Thank god for my failure I think now. Thank you, with all the gratitude we little humans can muster, for the hurt, the shame, the failures of those around me to protect me from life and for the runaway emotions that threatened to drown me as sure as I knew the day would end. It is in that place, where I can accept myself in shadow and light, that my heart opens further and the thing I perceive as having the power to destroy me actually becomes the wisest teacher of all.

winterline, gap year, teaching

What is this quality, and how can I stand in front of young people and teach them that failure is OK, but self-doubt is not? The decisions you make, what happens to you, is not who you are. What matters is how you move forward and the determination with which you fight to be the best person and create the best world possible. That is worth walking through the self-determining gauntlet of failure.  Attitude, then, fundamentally shapes how we perceive what comes to us in life, both good and bad. Our downfalls and shortcomings quickly become our greatest asset for empowerment and inspiration.

Fundamentally we are all sitting in exactly the right place at exactly the right time to become our biggest and best selves.

The perception of inadequacy or misappropriation a terrifyingly delicate and appropriate place from which we can let go and enter the current of our own lives.

The external, that piece that we claim as our personality and deeply personal aspects of our lives, is driven by choice and intimately linked with our egos that are designed to protect and serve at all costs. When then, does our creation of safety and familiarity become the aversion to the exact thing that will allow us move into deeper connection with self and other?

Go out of your way to take a risk, to engage the notion of failure within your world view. I promise you will discover qualities of yourself that you didn’t know and you will find a greater place from which to decrease the isolation of being a modern human being. The only thing separating us from our biggest selves might be holding our potential for failure in one hand and our potential for greatness in the other.

winterline, gap year, teaching

There’s a Jesuit idea that has at its core that the place you will encounter the most growth – spiritually, emotionally, and communally – is that place you resist the most. It’s confrontation on a personal level where our fears and self-doubt meet the external stimuli that gives those darker or harder places within us life.  Thomas Merton once confided in his mentor his fears of entering the priesthood and his strong aversion to death and dying. In response, his mentor decided the best place for him to grow was to be of service within a hospital in a hospice ward.


Leave a Comment

Most Popular

20 Colleges That Encourage A Gap Year

By: Julian Goetz | April 1, 2017
Topic: Education, Gap Year Planning

Taking a gap year to pursue new experiences, goals, and worlds before or during college is more (...)

Location Spotlight: Estes Park, Colorado

By: Jess Bonner | September 22, 2017
Topic: Location Spotlight, Uncategorized

Our 9 month gap year program begins at YMCA of the Rockies located in Estes Park, Colorado. (...)

How to Plan A Gap Year Like Malia

By: Olga Khaminwa-Joseph | March 15, 2017
Topic: Education, Gap Year Planning

The internet exploded when America’s favorite daughter, Malia Obama, announced she'd defer (...)