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From Both Sides

Rows and flows of angel hair
And ice cream castles in the air
And feather canyons everywhere
I looked at clouds that way
But now they only block the sun
They rain and they snow on everyone
So many things I would have done
But clouds got in my way
I’ve looked at clouds from both sides now
From up and down and still somehow
It’s cloud illusions I recall
I really don’t know clouds at all

– Joni Mitchell

On most days, I make decisions about the future of which I have at most maybe three hours of foresight into. Sometimes by lunchtime, I want at least a few do-overs. “I didn’t realize we were supposed to know everything by our second rodeo,” designer Alli Addison quips. “… Seems like a low number of rodeos.” As humans, it takes us a while to figure things out: We learn by doing, and looking back gives us even greater insights.

Regret gives you a chance to see things from both sides. The one you lived through, and the retrospective. Pausing to reflect on what was or has been allows us to see what we’ve learned from the vantage point of where we are now. As Dan Pink asserts in this podcast conversation and in his latest book, The Power of Regret, regret is a clarifying emotion that is also instructive about how to lead a better life.

In this conversation with Jerry, the two weave along two themes — one of taking time to pause, and one of the big opportunity in reviewing regrets. In some ways, they go hand in hand. When we slow down to a halt, we give ourselves a chance to reel through what went well, what didn’t, and what we’ve gained.

“There is a power in the standing still, there’s a power in pausing,” Jerry notes. “There’s a power in just reconsidering.”

Give yourself a pause, and reflect upon:

  • If you look back over your past and see mistakes, what were those moments? What do you wish you would have done differently? How do you approach similar things now?
  • After seeing things from both sides, in what ways or in what instances do you feel, metaphorically, like “you don’t know clouds at all” (to quote Joni Mitchell)?
  • What set of metrics are you holding yourself to that is a rigid external model of success? (For example: if you’re not progressing in a straight trajectory up and to the right, that somehow you’re missing the mark.)
  • How do you mistake movement (or productivity, or performance, or doing things) for meaning? What has been a more true path and pace of your life? 
  • What have been the most meaningful moments in your life? What was it about those moments that made them so for you? What inside of you told you that these were meaningful? 
  • What part of your current life setup, or current beliefs and metrics, do you want to dial back to match your true pace, your values, your definition of success?


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