How and Why to Get Better at Failing

The ability to “fail well” is a skill we all need if we want to accomplish what we set out to do. Failing is really a cornerstone that all other skills are built on.

Of course everyone has failed. Sometimes in highly visible ways. It is hard to get through this life without major setbacks. It could be in the form of losing a large sale. Or a failed startup. It could be not getting into the school you wanted. Or a close relationship that didn’t work out.

There are also the small, repeated failures we all experience on the way to learning something new. No one, out of the gate, kicks 50-yard field goals or plays Bach concertos. Lots of practice is required to learn complex skills and that practice involves not doing it correctly—failing, in a sense—until you get it right.

But experiencing failure is not the same as being skilled at it. What does it mean to be skilled at failing? Of course I am not suggesting you get better at failing by running around screwing things up. Rather, there are ways to respond differently when you fail to achieve what you had hoped. The ideas that follow are based on a talk Pema Codron gave at the Naropa Institute in 2015: “Fail, Fail Again, Fail Better.” I cannot recommend it more highly.

As with any skill, getting better at something often involves figuring out what not to do. Concomitant with failing are the intensely uncomfortable, roiling emotions we experience. We often feel raw, vulnerable, ashamed and scared. Sometimes we may even feel a sense of rage, a desire to want to lash out or seek revenge.

This is where Pema begins. She notes that the first typical response to those feelings is to blame others or outside circumstances. This is quite understandable and normal. If we blame others and the situation then we can avoid some of those awful feelings. “I didn’t play badly, I lost because of the referees.” Or, “I couldn’t have succeeded on that project because she was out to get me.”

When blaming others begins to lose steam and vulnerability starts to creep in, the second typical response is for our Inner Critic to rise up and attack. It is the voice inside you that says, “You suck. Others are finally seeing what ‘I’ knew all along. Why don’t you just give up?”

Pema’s recommendation for failing better is to not push any of this away. Instead, get better at holding all the raw emotions in your heart. Become capacious and sit with the feelings, just as they are. One approach she suggests is to get curious about them: What are the feelings, exactly? Where do I feel them? What is the story that goes along with these feelings? Is this a new story or an old story? Where did that story come from?

Why on earth would anyone want to get into the feelings around failure? Isn’t denial better? What could possibly be served by going into painful feelings rather than avoiding them?

Pema’s address outlined three real benefits of increasing our equanimity in the face of painful feelings. First, many addictions are the outgrowth of avoiding painful feelings. Some are simple, relatively harmless addictions like constantly checking email, playing Candy Crush for hours or binge watching TV to avoid facing the feelings of failure about a situation or a job or a relationship or facing your own feelings of helplessness or lack of self-worth.

Of course there is nothing wrong with a little Candy Crush. But simple avoidance strategies can turn into serious, life-threatening problems with drugs or alcohol or gambling. Developing the ability to not have to push painful feelings away makes us less susceptible to addictions of all types.

A second reason for not pushing painful feelings away is that in the space of those feelings of vulnerability and loneliness is the chance for real heart-to-heart connection with others. Sitting with painful feelings creates a receptivity…what the Japanese call mono no aware…empathy toward all things. In a similar vein, my favorite line in the movie Almost Famous is “The only true currency in this bankrupt world is what you share with someone else when you’re uncool.”

Getting better at failing does not mean you are going to fail more. Nor does it mean you are going to be spared from failure or fail less. Therefore the third reason for getting better at failure is so that the next time the failure wave rolls in—because roll in it will—it won’t knock you down as often or for as long.

As we begin to build more skill around failing, we spend less energy wrestling with its attendant emotions. This translates into greater wherewithal to pursue the endeavors we cared about enough to risk failing at in the first place.

Dennis graduated from the Professional Coaching Course in 2015. You can read more from him on his blog.

New Ventures West