SourceFebruary 18, 2026clippings

Philosopher's Notes | The Power of Regret

The Power of Regret

How Looking Backward Moves Us Forward

About the Book

Brian's take

Dan Pink is an extraordinary storyteller and science synthesizer, and this is the fourth Philosopher’s Note we’ve created on his work, following Drive, When, and To Sell Is Human. In The Power of Regret, Pink dismantles the “no regrets” myth and shows how regret, handled well, can sharpen decisions, elevate performance, and deepen meaning. Big Ideas include the science and value of regret, the four core regrets (foundation, boldness, moral, connection), self-compassion (kindness, common humanity, mindfulness), what to do with regrets through practical repair and perspective tools, and redemption as the ultimate narrative.

“Regret makes us human.”

Regret makes us better.

Daniel H. Pink

“Too much negative emotion, of course, is debilitating.”

But too little is also destructive.

Daniel H. Pink

“A look at the research shows that regret, handled correctly, offers three broad benefits.”

It can sharpen our decision-making skills. It can elevate our performance on a range of tasks. And it can strengthen our sense of meaning and connectedness.

Daniel H. Pink

“There is a crack, a crack in everything.”

That’s how the light gets in.

Leonard Cohen

“This is one of the central findings on regret: it can deepen persistence, which almost always elevates performance.”

Daniel H. Pink

“If we know what we truly regret, we know what we truly value.”

Regret—that maddening, perplexing, and undeniably real emotion—points the way to a life well lived.

Daniel H. Pink

“After a few years immersed in the science and experience of our most misunderstood emotion, I’ve discovered about myself what I’ve discovered about others.”

Regret makes me human. Regret makes me better. Regret gives me hope.

Daniel H. Pink


Regret, the Science and Value Of

24:55

Introduction

From the book

“Embedded in songs, emblazoned on skin, and embraced by sages, the anti-regret philosophy is so self-evidently true that it’s more often asserted than argued.

Why invite pain when we can avoid it? Why summon rain clouds when we can bathe in the sunny rays of positivity? Why rue what we did yesterday when we can dream of the limitless possibilities of tomorrow? This worldview makes intuitive sense. It seems right. It feels convincing. But it has one not insignificant flaw. It is dead wrong. What the anti-regret brigades are proposing is not a blueprint for a life well lived. What they are proposing is—forgive the terminology, but the next word is carefully chosen—bullshit. Regret is not dangerous or abnormal, a deviation from the steady path to happiness. It is healthy and universal, an integral part of being human. Regret is also valuable. It clarifies. It instructs. Done right, it needn’t drag us down; it can lift us up. And that is not some gauzy daydream, a gooey aspiration confected to make us feel warm and cared for in a cold and callous world. That is what scientists have concluded in research that began more than half a century ago. This is a book about regret—the stomach-churning feeling that the present would be better and the future brighter if only you hadn’t chosen so poorly, decided so wrongly, or acted so stupidly in the past. Over the next thirteen chapters, I hope you’ll see regret in a fresh and more accurate light, and learn to enlist its shape-shifting powers as a force for good.”

Brian's Notes

I’m a very big fan of Dan Pink.

He’s an extraordinary writer who integrates great storytelling with compelling science.

This is the FOURTH Note I’ve created on one of his great books. Check out my Notes on Drive: The Surprising Truth About What Motivates Us, When: The Scientific Secrets of Perfect Timing, and To Sell Is Human: The Surprising Truth About Moving Others.

I read this book during my little mini-sabbatical last year in which I read 101 books in 101 days. It, along with The Top Five Regrets of the Dying (Notes soon!), was deeply moving.

The book has three parts.

We start with “Regret Reclaimed” featuring chapters like “The Life-Thwarting Nonsense of No Regrets” and “Why Regret Makes Us Human.”

Then we move on to “Regret Revealed” in which we learn about the FOUR regrets we want to understand: “Foundation Regrets, Boldness Regrets, Moral Regrets, and Connection Regrets.” We conclude with “Regret Remade.”

If you’re human, you have regrets.

This book shows us how to use them to create our best lives. (Get a copy.)

It’s PACKED with potentially life-changing Big Ideas and I’m excited to help you apply some of my favorites to your life TODAY so... Le’ts get to work!


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