Reboot Podcast Episode #160 – Learning From Regret – with Daniel Pink

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.


Daniel Pink

Daniel Pink


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Episode Description

What can we learn from regret? Regret gives us chance to see things from both sides. The experience we 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 pair explore two themes — taking time to pause and the big opportunity in reviewing regrets. In many 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.

Jerry on The Tim Ferriss Show | #84 – How Have You Lived Your Life – with Parker J. Palmer

Show Highlights

Top Quotes:

“I think that mistaking motion for meaning is an international epidemic. Not only do we need to see ourselves as moving up into the right in this constant experience, but we need to see ourselves as a kind of a machine constantly outputting in order to quiet the sense that I’m nothing unless I’m producing.” – Jerry Colonna

“You have some agency in the conditions that you’re living in, so what is it about these conditions that you have created that you want to dial back?” – Daniel Pink

“There was this gap between our perception of this emotion and the reality that science was telling us about this emotion. I found that intriguing.” – Daniel Pink

“The whole notion of regret has been cloistered, it’s been made taboo. Everything I’ve done over the last couple of years in doing this research suggests that this is something people want to talk about. This is something that is actually healthy for people to talk about.” – Daniel Pink

“Why is something that’s so unpleasant so ubiquitous? And the answer is that it’s useful because regret does things that other emotions don’t do. What regret does is that it clarifies what we value and it instructs us on how to do better.” – Daniel Pink

“Real courage is looking your regrets in the eye and doing something about them.” – Daniel Pink

“When someone who has power has the ability to internalize regret, to internalize and confront the mistakes, we create the conditions of safety for those underneath them to be able to do the same thing.” – Jerry Colonna

“No regrets and don’t look backward is a terrible blueprint for being effective. It’s a terrible blueprint for being a contributor. It’s a terrible blueprint for fashioning a life well lived. It is delusional and it’s ineffective.” – Daniel Pink

“When people tell you what they regret the most, they’re telling you what they value the most. And that’s another way that regret is clarifying and instructive about how to lead a better life.” – Daniel Pink

“A life well lived is a life where we are kind, where we have people who love us and who we love and where we treat people with respect and we treat people with dignity. We treat people with kindness.” – Daniel Pink

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