Regret. We All Need a Little More of It…wait. What?

I recently listened to Brené Brown’s Dare to Lead Podcast, Brené with Dan Pink on The Power of Regret. In the interview, she asks Dan Pink about the research he did for his newest book, The Power of Regret: How Looking Backward Moves Us Forward. It was one of the best interviews/podcasts I’ve heard in a while. I’ve ordered the book and can’t wait to share more of what learn from reading it. Until then, I’ve got something else to share. 

After finishing the podcast, I went straight to YouTube looking for more of Dan’s takeaways from his research and I came across the video below.  It’s a summary of some of his key findings and it’s fascinating. I encourage you to watch the video for yourself, but first I want to share why Dan’s research is so helpful to those of us in our 40s, trying to make sense of where we are in life. 

After scouring the data Dan found 4 major regrets that he said all people share, regardless of race, gender, nationality, etc. They are Foundation Regrets, Boldness Regrets, Moral Regrets, and Connection Regrets

Foundation Regrets

These are the regrets we all have when we realize we could’ve done more to lay a solid foundation for our future, back when we were younger. If you’re in a place where finances cause you stress, you’ve probably asked yourself, why didn’t I start saving money sooner? Or maybe you’ve had some health-related issues that could’ve been prevented by better choices 10 years ago. And if you find yourself looking for a new career at 40, you’ve probably questioned your past choices and had that moment where you wish you would’ve taken school more seriously.  

We all look back on the time we wasted when we were young and think, “If only I’d done the hard work then” I’d be in such a better place now.

Boldness Regrets

We can all think back on a time when we wish we had been more bold. Whether it’s that person we wish we’d asked out on a date but were too shy. Or that business idea we had but were too afraid to take the risk to venture out on our own. It’s also the situations where we wish we would have asserted ourselves more, where we know we should have spoken up. 

In life, we can play it safe, or we can take the chance. Dan says that these boldness regrets are the moments we look back on and say, ”If only I’d taken the chance.”

Moral Regrets

How many times in life have you been at a juncture when you had to choose between doing the right thing or the wrong thing? Most times the right thing is the harder thing to do, but we still know it’s what we should choose. And yet, sometimes we take the easy way out and make a bad decision. 

These are the moral regrets. Whether we stole something, didn’t stand up for the kid being bullied, cheated on that test, or even worse, a spouse. These are the moments in life we look back on and wish, “if only I’d done the right thing.”


Connection Regrets

The final one, Dan argues, is the most difficult. These connection regrets are most painful because they involve the people we love. We all need love and connection. So, when these things break down, it’s hard. And yet we’ve all felt these regrets when we don’t spend as much time with our parents or siblings as we should, or when old friendships drift apart, or for others when a marriage fails. 

Dan says these are the moments where we think about reaching out to someone but then tell ourselves the lies that they don’t care about us, they’re too busy for us, and wouldn’t want to hear from us anyway. He says, make the call, or go and visit. If you don’t, you’ll be saying to yourself, “If only I’d reached out.”

Regrets. the Photo Negatives of the “Good Life”

As Dan worked through the data, noticing patterns, he made an insightful connection.  He pointed out that these 4 Regrets act as a photographic negative of the “good life” we all long for. If we can come to a better understanding of the things we regret the most, we have a clearer picture of what they value the most!

So, instead of buying into the common misperception that regrets are a bad thing, I’m arguing along with Dan Pink, for a new approach. I think we should lean into our regrets, reflecting on why we have them, and then use those insights to help us more clearly see and focus our attention on the things we value the most. 

If we start this work now, our future selves will thank us. Instead of looking back and saying, “No regrets,” we’ll be able to reflect with thankfulness on the lessons our regrets have taught us. 

2 thoughts on “Regret. We All Need a Little More of It…wait. What?”

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