Courage and Failure

It takes courage to embrace the possibility of failure. It isn’t failure itself, but the fear of failure that keeps us from stretching or going beyond our comfort zone. When something inside us suggests the possibility of “yes,” fear of failure compels us to say “no.” Fear of failure makes us anxious and uncertain. We do what we can to avoid it – take the safe route and stick to what’s expected. And we tell ourselves that taking the safe path is the reasonable thing to do. It certainly seems reasonable. But it can also be about listening to the fear.

paper bag thinking.com2

From the site

On the other hand, we can see that our lives are about the choices we make. Which path do we pursue? What do we bring with us on the journey? Courage helps us face our fears – face the anxiety of the unknown and go forward. Courage is about embracing risk and accepting that our choices may include the possibility of failure.

“Living My Most Fearful Self”

If you’re not familiar with her work, I’d like to introduce you to Debbie Millman.

Debbie Millman from The Great Discontent website

A prolific designer/educator/author/interviewer, Debbie has been exploring the creative life in terms of risk, failure and courage. From an interview on The Great Discontent website:

From the Portable Talks website

My first ten years after college were experiments in rejection and despair. I knew that I wanted to do something special but, frankly, I didn’t have the guts to do anything special. When I graduated, I didn’t feel confident enough, optimistic enough, or hopeful enough to believe that I could get what I really wanted. I wasn’t living what I would consider to be my highest self—in fact, I was probably living my most fearful self.

She goes on to talk about the role serendipity played in her life.

My whole life has been one thing leading to another, leading to another, and then another. It has been completely circuitous and mostly unplanned. Lately, I have been thinking a lot about these chance encounters: those elusive happenstances that often lead to defining moments in our lives.

Those Elusive Moments of Serendipity

Many of the amazing opportunities I’ve had in my career came from those same elusive moments of serendipity. More than that, the best assignments were the ones that scared me – the occasions when I said “yes” and then had to draw my own road map on how to get it done.

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Title capture from the PBS series “Mini-Dragons’

I was once asked if I would go to Japan to teach the NHK TV documentary team how to craft their stories in the feature documentary style. I would have to show them how to structure their documentaries without narration or talking heads and to create dramatic visual scenes with a beginning, middle and end – in other words, to show, not tell the story. I knew from the start I would be walking into polite but hostile territory and that it would be an enormous challenge to make it work, but I said “yes” despite the fact that I’d never done anything like that before.

It was a great time of personal growth. I stretched the limits of what I thought I could do and ended up surprising myself. Yes, it was difficult and challenging and often I was running scared, but it taught me that it’s more important to say “yes” and accept the fear than take the safe route, avoid failure, and drift into boredom and mediocrity. I’ve done both and doing the scary thing yields better results – when you work at the edge of your comfort zone you feel better about yourself and more alive. It’s also more fun.

A Cool Video on Failure, Safety and Courage

I want to get back to Debbie Millman and her video “Fail-Safe” exploring risk, failure and courage. There’s a link to it a little farther down the piece.

From the Adobe Inspire website

I really like the video’s message and its simple but effective approach to telling a story – her story really. Here’s a quote that launches the story:

From the Adobe Inspire website

I lingered at the intersection peering deep into my future and pondered the choice between the secure and the uncertain, between the creative and the logical, between the known and the unknown.


I think many of us can harken back to a moment when we confronted a choice about which direction to embrace – the easy or difficult path. Underlying the uncertainty was our fear of failure v. our willingness to embrace risk. Looking back, she talks about her own fear of failure and insecurity, the choice she made and where it led her.


From the Adobe Inspire website


I feel like everything I’ve done has required some risk. I don’t think you can achieve anything remarkable without some risk.

Her video “Fail-Safe,” is from the Fast Company Design website via the Inspire.Adobe site.

You can click on the link to watch the video here.

The Road Less Traveled

We often admire entrepreneurs, leaders who show courage and other risk-takers. Still, it takes gumption and grit to say “yes” instead of “no.” site

From the Die Line website

Risk is actually a rather tricky word because humans aren’t wired to tolerate it very much. The reptilian part of our brains wants to keep us safe. Anytime you try something that doesn’t have any certainty associated with it, you’re risking something, but what other way is there to live?


It’s a lot easier to look back at your life and evaluate your decisions than be standing at a crossroads and know which way to turn. As I told my kids growing up, it’s more important to make a decision. If it turns out not to be a good choice, then you can correct it with another decision. I’ve also found that taking the hard road, embracing the difficult route that causes you to stretch and push your comfort level, yields a more satisfying outcome. Yes, you may stumble, make mistakes and perhaps fail. But echoing Debbie Millman, how else do you learn and grow?

I’ll let Robert Frost make the final argument:


Robert Frost from the Heavy Laden Bookshelf website

The Road Not Taken

Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;


Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,


And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.


I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.


Have you faced similar issues or choices? What’s your experience? Leave a comment and let me know.