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Failure Sucks. But We Don’t Need to be Afraid of It.

What Would You Do If You Weren’t Afraid?

Photo by Meiying Ng on Unsplash

We Were All Unafraid At One Point

“The three boys came in, four-year-olds with tea towels on their heads, and they put these boxes down, and the first boy said, ‘I bring you gold.’ And the second boy said, ‘I bring you myrrh.’ And the third boy said, ‘Frank sent this.’”

Maybe It’s Unavoidable

One of the reasons why mature people are apt to learn less than young people is that they are willing to risk less. Learning is a risky business, and they do not like failure. — John W. Gardner, Self-Renewal: The Individual and the Innovative Society

“By resisting the beginner’s mind, you make yourself more prone to repeat yourself than to create something new. The attempt to avoid failure, in other words, makes failure more likely.”

Photo by Joshua Sortino on Unsplash

Flawed is Human

“Whether you fear it or not, disappointment will come. The beauty is that through disappointment you can gain clarity, and with clarity comes conviction and true originality.” — Conan O’Brien, Dartmouth’s 2011 Commencement Address

“In one sentence, he lifted me, put me back on my feet, and taught me that leaders can let you fail and yet not let you be a failure.”

Failing is Inevitable. Failure Doesn’t Need to Be.

“Bravery is always more intelligent than fear, since it is built on the foundation of what one knows about oneself: the knowledge of one’s strength and capacity, of one’s passion.” — Nicole Krauss, responding to Vincent Van Gogh’s 1884 letter on fear and risk-taking.

“We become what we do if we do it often enough. We act with courage, and we become courageous. We act with compassion, and we become compassionate. If we make resilient choices, we become resilient.”

“The fool, with all his other faults, has this also, he is always getting ready to live.”



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Jake Wilder

Jake Wilder


I don’t know where I’m going. But at least I know how to get there.