Failure School: How to Succeed at Failing


99.99999% of your fears
live only in your imagination,
in anticipation, and in memory.

Even if the ‘worst’ happens,
you’ll find yourself dealing with it in the moment,
responding from a place of presence.

You don’t have to deal with it now.
You’ll handle it then.

And who knows:
The ‘worst’ thing may turn out
to be your greatest teacher,
your most profound call to awakening,
an invitation to the kind of courage
of which you’d never thought yourself capable.

Fear isn’t your enemy,
but a signpost.

Breathe into the moment.

– Jeff Foster



I just googled the definition of “failure.”  Here’s the most comprehensive and concise meaning I found: “the omission of expected or required action.”  Sounds pretty benign, right—so matter of fact?

The kind of fear of failure I’ve experienced along the way has been a far cry from this bland “omission” situation.  Quite the contrary; it’s been a crippling and immobilizing force that’s stunted growth, joy, and relationships.  From the anonymous surveys many of you were total champions for completing last week, I know I’m very much not alone.

I’m fascinated by this unruly expectation we place on ourselves to avoid failure. So much so that I’m developing some additional resources for us to dig into around this work on a deeper level.  For now though, I want to pepper your thoughts with some key insights that have become a lynchpin shift in my understanding and approach to failure.

Expectation Shift

The operative word in the above definition is certainly “expect” not “omission” as it relates to our study here.  Why?  Well, simply put, because it’s the subjective that we tend to personalize, not the objective facts.  I either deliver or I don’t and surely my life’s worth and value aren’t tied up in that slice of history.


I’ve bombed so many performances it might lead you to wonder if I had a screw loose for continuing in my early music days.  For some ungodly reason, I kept going even though it felt like cruel and unusual self-harm.  Strangely, no one ever told me I sucked or bombed it or should definitely not quit my day job.  I only received encouragement and kindness.  I realize, we are in the South y’all.  Nonetheless, I’m a pretty good read and they seemed genuine.


We’re so tightly wound and attached to the narrow expectation of who we should be and how we should perform that we lose sight of the incredibly vast and curious horizons that come along with the fall.

Have you ever watched a toddler on the cusp of walking? First of all, it’s high and hilarious art.  Secondly, the ONLY way their tiny muscles are made stronger is by falling and getting up—over and over and over again.  And we “ooh” and “ahh” and gawk like grown chimpanzees about to be fed at the circus in response.  Go figure.


So why is it so terrifying to fail?  I believe it’s because we are afraid of the way we will treat ourselves and as a result feel in response to our perceived failure–our missing the mark.  Like the poem states, nearly every shred of our fears live in the stories we make up about them, our imagination. Our fears are rarely tethered to reality and we drive the shame ship of our failure…we’re the culprit!  Sure, the outcome is humbling at first, but by elevating our belief about failure, we construct a new brain pathway or go-to storyline that facilitates self-compassion instead of self-flagellation.  We don’t evolve by playing it safe in a mole hole, but by staying present at the crossroads of failure and opportunity.

Know the Difference

Before you go poking holes in my sunshine, I’ll clarify an exception to the rule. There are two types of failure, and I refer to failure at this point as something necessary for growth and success.

There is all-in failure and half-ass failure.  All-in failure is when we’ve shown up,  given our all, and  fully engaged in the pursuit at hand, yet for whatever reason didn’t quite make the cut.  The passion and effort are there, yet the outcome is not—yet anyway.

Half-ass failure, as you might imagine, is missing the mark without giving it a fighting, bleeding-heart chance.  We’ve all been there, yet it’s not a  helpful pattern as it ultimately becomes self-fulling prophecy.  Oftentimes, this is simply a good indicator that we may not really want what we’re limping for and redirection is necessary.

Failure File

This homework might blow your mind and/or cause you to become extremely frustrated with me.  Both are fine, just keep me in the loop there. 

I’m convinced if we’re not wholeheartedly failing, we’re not stretching ourselves enough.

I recently heard a podcast interview with a man (whom I couldn’t catch his name for the life of me) talking about this very concept.  He’s a big wig coach who guides super successful executives into their highest potential.  He gave his clients strict homework to fail at least five times a month and record those failures in a specified file in their office, a failure file.  (Mic drop.) I nearly turned it off.


I wrestled with this notion for a couple hours, and quickly became OBSESSED.  Fickle, yes.  I’ve started experimenting so as to really put myself out there in ways that seem uncomfortable and awkward.  You know what?  In the process, I’ve accomplished some pretty daunting goals I’ve had staring me down for months now and feel a noticeable momentum shift.  There’s something to this.

And so I dare you.  Start your own failure file this week and go for one “all-in fail” to add to it.  What comes up for you even thinking about this stuff?  Dig into to; dance with it.  It surely won’t kill you.  If nothing else, your world will be so much bigger for playing along.  Go ahead, give yourself total permission, or homework,  to fail.  There’s wide-open freedom and life in that movement.

A man we know and love called Winston Churchill said it well.  He’s a mixed bag of courage, successes, failure, bullheaded stubbornness, and legend all in one. His stories and words have a vibrant life of their own well after his last breath.  Now that’s gumption.

“Success is not final. Failure is not fatal.  It is the courage to continue that counts.”

-Winston Churchill

Love & Gratitude,