Why I Hope to Fail

Why I Hope to Fail

My recipe for never settling

December 11, 2020


There are certain quotes that I have stumbled across that set my soul on fire. These quotes are like a spell that when read aloud, ignite something deep within me. They speak directly to the part of me that remembers when I was a small child with big dreams. When everything was possible and the future was unlimited. Before anyone told me to be realistic or to stop daydreaming, reading certain quotes make me remember.

I was sitting at the kitchen table, minding my own business when I first read Teddy Roosevelt’s famous quote:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

I didn’t realize it at the time, but this quote would change the course of my life forever.

My Greatest Fear

When this quote found me, I was trying to muster up the courage to quit my job and follow my dreams. But I was scared. I was so terrified of failing that my fear was forcing me to do something that I swore I would never do. My fear of failure was forcing me to settle.

I was settling for a normal life, a normal job, and a normal impact on the world. I could hardly look at myself in the mirror because every day that went by, I knew I was letting the highest version of myself down.

But then this quote found me. And it made me realize that there was something that I feared even more than failure.

My greatest fear was not that I would try to follow my dreams and fail, but that I would never try at all.

The moment I read this quote I realized that nothing could be worse than the regret of never even trying. Imagining myself laying on my deathbed, full of regret and wishing that I would have had the courage to go for my dream was unbearable. So I promised myself that I would never allow myself to be categorized “with those cold and timid souls who neither know victory nor defeat.” Regardless of the outcome, I decided that I was going all-in.

Freedom to Fail

Since making this commitment, I have been able to completely reframe how I view failure. Instead of seeing failure as something shameful and negative, I now look at my failures as evidence that I am giving life everything I’ve got.

This is the reason that I hope to fail at many things throughout my life. Because each failure will be a reminder that I am pushing myself beyond my comfort zone. It will mean that I have left nothing on the table, no gas in the tank, and most importantly, that I never settled.

“Life should not be a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming WOW! What a ride!” — Hunter S. Thompson

Moving Forward

The moment I gave myself permission to fail was the moment that my fear of failure vanished. The whole world seemed to open up once I got out of my own way and began to view the world through a lens of possibilities instead of potential threats.

Since I changed my relationship to failure I have:

  • Quit my job
  • Co-founded a nonprofit
  • Started a podcast
  • Told the world (and myself) that I am a writer
  • Started training to become a Neuro-transformational coach

All of these ventures have scared the hell out of me, but they have given me something that is truly invaluable. They have shown me that my fear of failure can be overcome by accepting failure as a critical part of my personal growth.

Now that I acknowledge that failure will be a necessary part of my journey, I feel like a huge weight has been lifted off my shoulders. Giving myself the freedom to fail has allowed me to start living a life that I am truly in love with and has ensured that I will maintain my promise to never settle.

Most of all, it brings me a deep sense of peace knowing that I had the audacity to listen to my heart. Ever since I made my leap of faith and hurled myself into the abyss, I wake up smiling because I know that I am living a life that is regret-free, full of purpose, and 100% my own.

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