Regrets Are Great

Photo by Edge2Edge Media on Unsplash

Matty Kerr is co-creator with John Brancaccio of The Working Experience. He is also a filmmaker and published author. Listen to our podcast on iTunes and Spotify and visit our website: for videos, merchandise and more. You can also find us on Facebook, Linked In, Instagram, and Twitter.

“Regrets…I’ve had a few…”

When you lay your head on the pillow at night you should think:

“Man, I should not have said that.”

“Jesus, I should not have eaten that.”

“Why did I wear that?”

“Good God, I could have been killed!”

If you are totally at peace with yourself and the world around you…then, come on man, you ain’t really living. You can’t go through your life walking on egg shells and plotting every little move and watching everything you say. That is how you turn into a neurotic mess. That is how you become the most boring person alive. And terribly dissatisfied with life.


No one really trusts a person who can’t let it go and make some mistakes. Who wants to be around someone who always plays it safe, who never blurts out something completely inappropriate and utterly hilarious?

Who wants to be sixty years old and have no stories? How do you live like that?

I have a broken shoulder that never healed properly because of a drunken bicycle accident. I got my nose broken in a bar brawl in Colorado. I made a short film two years ago that cost around $30,000 and it went nowhere.

I’ve embarrassed myself more times than I can remember. Do I regret these things? Sure. But I’d rather regret them rather than they never happened.

Say it! Eat it ! Wear it! Try it!

Our mistakes, our regrets, our scars…these are what give us character.



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M. Francis Enright

Co-creator and cohost of The Working Experience Podcast. We explore what people do for work, how they do it and how they feel about it. Twice a week!