The Myth of Being Comfortable with Failure

If you're comfortable with failure, you're failing wrong

Special Tactics officer candidates carry a Zodiac boat to the shore during a selection at Hurlburt Field, Fla., Oct. 21, 2014.

I recently received a request from a popular online publication to write about how being comfortable with failure, increases success. I told them no and here’s why.

The short answer is, it doesn’t. I’m not comfortable with failure; in fact I absolutely hate it. My family and employees can attest that I agonize over mistakes and failures. I become withdrawn and will ruminate on what could have been done differently. I go through an emotional roller coaster of blaming others, blaming the situation and eventually land on all the things I did wrong.

If you're comfortable with failure, you'll never be successful. We only learn from failures if they make us uncomfortable, massively uncomfortable.


If you’re comfortable with failure, you’ll never be successful. I would even argue that the most unsuccessful people you know have become too comfortable with failure. There is a major misconception out there that somehow being comfortable with failure will enable future success, because we learn from failures. Well guess what, we only learn from failures if they make us uncomfortable, massively uncomfortable.

The more uncomfortable the failure, the more incentive we have to learn from it. A majority of our lives is a matter of experiencing discomfort, desiring to remove that discomfort and learning how to avoid it in the future. Success from failure isn’t about being comfortable; it’s about not fearing the discomfort. Experiencing the discomfort motivates us to remove the pain by changing the way we do things in the future.

Our level of comfort or discomfort with a failure is rooted in a psychological principle called cognitive dissonance. Essentially, the discomfort we experience when our behavior or outcomes don’t match who we believe ourselves to be, this is cognitive dissonance. Dissonance or discomfort is key to changing behavior and is indicative of good mental health. When we fail, but do not experience discomfort (think cognitive dissonance), it indicates that we see ourselves as a failure. If we believe the outcome of failure is who we are, we have no reason to change our behavior. Nor do we believe we can change the outcome in the future.

There is a significant difference between being comfortable with failure and not fearing discomfort.


There is a significant difference between being comfortable with failure and not fearing the discomfort. What you want is to not fear the discomfort. I wonder if the misconception has developed because we brush over the difficulties of achievement and focus on the triumph. Don’t get me wrong, I think there are tons of stories about the challenges and failures achievers have faced before their success, but we romanticize those stories and quickly jump to the triumph.

I fall into this trap all of the time, even when I acknowledge the sacrifices my loved ones have made to enable my success. I say things like, “yea it was difficult, but worth it” or talk about working out of my basement in terms that don’t really capture the ugliness or misery. I don’t talk about the fights with those I care about most, the nights spent crying from loneliness because even though I’m surrounded by others they don’t share my vision, the agony of watching my children grow up via face time, the embarrassment of admitting a mistake that cost thousands of dollars and will require even more sacrifice from those who depend on me, the list is never ending. No matter how dramatic or forceful I am about sharing the pain of the journey, people will still focus on the end result. They will then be shocked when they experience the depth of discomfort for themselves.

Elon Musk gave us a glimpse of this in a Twitter exchange where he talked about “terrible lows and unrelenting stress”. Unrelenting stress is one of the best ways to describe the life of an entrepreneur or achiever, if you’re constantly pushing yourself, your employees and your organization, the discomfort will never go away. This is the definition of a positive feedback loop; something that reinforces itself and produces positive behavior in the future. When you push for achievement, you feel discomfort, when you feel discomfort you push to grow, when you grow you push for achievement…and the cycle repeats itself. Those who are comfortable with failure never receive reinforcement and the cycle breaks itself.

So, if you find yourself comfortable with failure, you’re either complacent or you haven’t failed big enough. Push yourself to do phenomenal things, know beforehand that if you fail, it will hurt, it will be incredibly uncomfortable…just don’t be afraid of that pain.

Success, Self Improvement, Psychology, Life Lessons

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