Professional Women

How Fear of Failure Teaches us to Fail

My education has ended.

I was in my hairdresser's chair Friday, talking about graduate school - how I briefly considered attending, how much I loved to learn, but (as it dawned on me as she snipped away my locks) how grateful I was that my 22 years of formal "learning" was over.

That's because my education was riddled with mistakes.

C's on tests, not scoring highly enough to count AP courses toward college credit, stumbling over topics I felt disenchanted to present, while everyone around me was gaining acceptance into top schools and was clearly more successful. 

You know what that led to? Constant anxiety, despair, self-esteem plunges, insomnia. Not to mention all of the physical manifestations of that mental state. 

That's because my education was riddled with mistakes. The biggest of them all: fear of failure.

Recently, I had the privilege of sitting down with Cake & Whiskey Magazine at their Pittsburgh HobKnob, a quarterly gathering of women in business, where a woman I have deeply come to admire in one evening introduced the topic of failure in the next generation. 

It wasn't long before we veered to discuss the current educational system - where failure is unacceptable, where learning behaviors are rigid and limited, and depicted as objective. 

My friend sitting next to me told me how this behavior translated into her career. When she began her job at Make-A-Wish, she felt timid to step outside of her comfort zone. One day, her boss gave her the motivating advice: "I need you to fuck up." 

That permission makes you feel...better. She allowed herself to feel open to changes, challenges, and mistakes. 

When we agree that failure is unacceptable, we are actually creating blockages to creativity, problem-solving, and success. 

I am more wildly successful than I could have ever dreamed. That's because I built my own life around what I was good at - creativity and a drive to help others.

I never learned that anywhere but inside of my own heart and intuition, where failure is not only inevitable, but subjective. 

I allowed myself to go after what I wanted. I didn't let others' ideas of success get in my way. 

Mostly importantly, I gave myself permission to be what I wanted, failures and all. 


1.) Get comfortable in a quiet space. If you're (unlike me) in a place with cooperative weather, sit outside. If not, sit in front of a window. Reflect on the beauty you see outside. The miracle that sits within it. 

2.) Write down a list of your biggest failures. They can be recent, failures you're afraid to make, or even leaps or choices you DIDN'T make because you were too afraid. Take a moment to really be honest with yourself. 

Set an alarm for three separate times throughout the day. When your alarm goes off, evaluate how you are holding yourself back through external perceptions of failure.

When did you not speak up, but wanted to share an idea? 

When did you put yourself down, to yourself or someone else? 

Where did you judge others based on society's ideas of failure?

When did you compare yourself to someone else, thinking they were better, or that you were?

"I have not failed. I have just found 10,000 ways that won't work." - Thomas Edison