The Entrepreneurial View of Failure

Author: Matt Morava

The following is a letter I recently wrote to a student who had experienced their first major failure in life and then almost let that failure snowball into a series of failures that would have concluded with their dropping out of college if they didn’t step up.

Learning to Celebrate Failure

Dear J,

I am happy to report that you have chosen to pass this class. Your paper was an open and honest appraisal of your journey as a student and leader.

I’m not sure which is ultimately harder in the long run, to experience success early in life or failure. We can learn a lot from failure: resiliency, self reliance, compassion, flexibility, innovation, and the importance of community and support but early failure can also lead to a sense of hopelessness, frailty, selfishness, desperation and a permanent survival modality. Conversely, early success in life can instill the importance of discipline, commitment, goal setting, making an effort, independence, integrity and accountability but early success can also inflate the ego to a point of arrogance and enshrine a sense of entitlement and belief that there’s something “special” or “unique” about you. Great leaders have a knack for failing forward and succeeding with humility.

What is humility?

“Genuine humility doesn’t come from thinking of yourself as small but as big, risking your creative power.” Thomas Moore

You J, have risked your creative power and the humility you may feel is your character actually getting some grit.

It was a pivotal moment in my life when I realized that I was failing at failing. Early in my career I was asked by an executive coach “What have you really failed at in life?” and I could point to what I considered a ton of failure at the time, hell I was on a baseball team that lost every single game for three seasons in a row, “I mean come on buddy don’t talk to me about failure!” but he just smiled and asked, “What is failure?” and I was stumped. I didn’t have a good answer.

I was terrified that failing meant I was a “loser” and so I never admitted failure. Never accepted it. (That kind of mentality sets you up for even bigger failures down the road and boy did I have some doozies waiting for me down the road.) It’s been a huge part of my personal journey to learn how to embrace failure and fail forward. I have learned that failure simply means having had the courage to go after what I loved, but that’s just my take on it. There are a ton of great books on the subject, amazing quotes that will inspire you, but what ultimately matters most is how you define it for yourself, because how you define it determines how you respond to it.

Now that you’ve tasted failure, what is it? What does failure mean to you?

Failure Is Real

I am not one of those people who will tell you that failure doesn’t exist or that the only true failure in life is giving up, as we do meet challenges in life that we don’t have the requisite variety to successfully match up against. You will compete against people who are smarter, tougher, stronger, faster, more likable, more talented, and/or better prepared than yourself. That’s a fact of life.

If in fact you are not continually faced with that level of competition, then you’d better put yourself out there and meet people who are smarter, tougher, stronger, faster, more likable, more talented, and/or better prepared than yourself because that’s how you grow.

There is flora and fauna out there that can drop kick you into oblivion in a heartbeat. There are forces, both natural and spiritual, that are greater than you at work in your life that can turn your best laid plans upside down in the blink of an eye. We can and do make bad decisions that take us down blind alleys and wrong turns. We can and do waste time and effort on projects and relationships that ultimately end up going nowhere. Our greatest successes can be undone with just one wrong glance. We have bad hair days, two left feet, and all thumbs. There are some out there who believe that failure is ultimately identifying too closely with a future that doesn’t exist, and there’s truth to that, but on a deeper level, failure is simply not living your true purpose. The poet David Whyte has speculated that maybe the only true failure in life is to keep attempting to live somebody else’s life as if it were your own.

This is where it gets tricky… are goals the same as true purpose?

I am also not one of those people who would tell you that failure isn’t difficult or doesn’t suck. It most certainly does suck and is difficult. Each failure in life is worthy of a grieving process; if only for a small period of time. What I love about your response to this failure is that you’re consciously choosing to fail forward. You’re starting to realize that no amount of failure can change your core values, your gifts, or your deepest of desires. You are not your identity. You are not your goals — met or not. Externalities are important, don’t get me wrong, we need some measure of success and recognition (we are social creatures after all) in order to experience happiness in life, but we are not the thing.

We Are Not Our Failures or Our Successes

I had a very odd childhood where I grew up with two very different families, in two very different homes, as my parents had divorced and remarried and one was poor and one was wealthy. It was an early spiritual lesson in the ego’s need of material identification as I toggled between what seemed like, from the outside, success and failure. In the US we tend to confuse wealth, beauty, and youth with success. We identify with the externalities regardless of what they are… “I am the $300K BMW” or the “$10M home” and conversely, “I am the person who rides the bus to work!” We are not our car, our house, our uniform, or our vacation spot. I found success and failure in both homes, regardless of what kind of car was in the garage.

Our Failures and Successes Reveal What We Love

I remember one time lamenting to my therapist that my life had gotten all turned around and that my parents were to blame. I had wanted to be a veterinarian and it was their fault that it didn’t happen. He said two things to me I’ll never forget:

You only have till you’re 17 yo to blame your parents. (I was 18 yo at the time.) And, “You are a veterinarian. A really good veterinarian at that.”

I remember at the time thinking that that was load of crock and some “New Age” bulls*it. I wasn’t a veterinarian. I hadn’t finished vet school. I wasn’t out all day in the barns taking care of sick horses and cows, but over the years I’ve come to appreciate his point of view. I’ve met women who longed to be mothers, but that didn’t happen for them and yet they are mothers to so many people around them. I’ve met men and women who wanted to be in the Armed Services and didn’t for whatever reason and yet are still warriors full of honor. I’m not a vet, but my love and care for animals is apparent in everything I do.

What you love, what you care about, your values, your gifts, your true purpose will be apparent in everything and anything you do. In fact, it’s unavoidable.

So to sum up…

Failure could be not living up to your true purpose, but that’s for you to decide.
Failure though is real, difficult, and does suck. You don’t have to like it. 
Failure and success are different disciplines, so learn to practice both.
Great leaders learn to fail forward. 
Great leaders can both fail and succeed with grace.
Successes and failures are expressions of our gifts, values, and deep desires.

I wish you well going forward as a student and as a leader. What you do from here is even more important that what you would have done had you been accepted into the program.

Reach out anytime.


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