Fail Boldly

I’m sure you’ve heard this thought before that if you’re going to fail, do so boldly. In other words really go out there and give it all you’ve got. If it doesn’t work at least you threw yourself into a volcano and left a nice blast rather than petering out after a 30 year career of counting paper clips adequately or surviving a life that’s so tiresome even the memory of your glory days make you feel like you’ve had too much Ovaltine and Nutella.

I’m pretty much an expert in bold failure and also in counting paper clips adequately. Anyone who denies that they’ve done boring jobs or had years they can’t remember is putting us on. Failing boldly and failing with a whimper are all part of it.

Still, I flame out in ways that make me blush remembering them. I’m oddly proud of that too. I recall the time I thought I’d be great on the drill team without realizing I am always a beat behind, was sure I crushed it in a debate that was actually thinly veiled nonsense or delivered a presentation that I thought would be moving but was so perplexing that even my friends said, “It’s okay, you’ll get after it next time.”

Then there are the small failures like not showing up for people, forgetting thank you and generally being a bore about my own stuff. Those are the actual cringe failures that stop me in my self absorption long enough to realize sometimes I’m a selfish jerk.


The small things are the big things. I would like to fail boldly inventing some technology that makes everyone feel loved. I wouldn’t make it but decades later someone would say my name and suggest I was close.

I could be the Tesla of love. Cool.

But really my important failures are far less grand. They are the failures of attention, of appreciation, of simple presence.

Here’s how I’d change:

  • Stop thinking ahead. Plant my feet where I am and be where I am.
  • Observe what’s around me and who is around me.
  • Make no assumptions.
  • Be open to being wrong
  • Notice. Everything
  • Fall in love with life and people and all of it every day, all day
  • Talk less

When I can do these things, here’s what happens:  Time with my sweet traveling friend who makes me see amputees entirely in a new light as he hops around the house, his prosthetic left like a sleeping pet, and smiles without provocation.

The experience of my friend who took the time to spill his profound wisdom about art over my unknowing brain until I could cry at a brush stroke.

Connecting with what it’s like to wake up transgender. Now I have a better feel for it based on people who refused to let me look away.

I’ve covered homeless people since the 1980’s as subjects but in these past five years I’ve become friends and had my heart opened and also broken.

I’ve always loved music but now I also have the experience of working for and with musicians and their precise and beautiful nature.

I’ve seen 60 year old choir boys cry and watched women toil in the sun dragging hoses across acres to keep their cannabis plants from dying while singing farm songs they learned in grade school. I stood with them in their work and saw their determination.

How could I know about these worlds without knowing the people in them?

Before I told stories but now I am part of the stories. I am living them too.

I failed boldly in trying to be someone with a story. I’ve tried writing it but it feels too self focused. But that desire drove me to harvest the stories of others and that big, bold failure is to date my biggest success.

Sometimes failing is the best thing you can do.



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