Daniel Pink is one of the world’s most influential thinkers on work, behavior, and human motivation. He is the author of seven New York Times bestsellers—including Drive, When, and The Power of Regret—books that have shaped how leaders, educators, and individuals approach purpose, timing, decision-making, and the emotions that drive us.

Across a career that spans law, politics, speechwriting, and two decades of groundbreaking writing, Dan has made complex research in psychology and behavioral science accessible to millions of readers worldwide. His TED talks have been viewed tens of millions of times, and his work continues to influence the way organizations and individuals think about performance, choice, and meaning.

In this episode, Dan and Subbu unpack why regret is not something to suppress but a vital emotion that helps us learn, grow, and make better choices. They also explore how to navigate today’s flood of information, the habits of good decision-making, and the human commonalities revealed by studying regrets from around the world.

We cover:

• Dan’s winding career path—from law school and politics to bestselling author
• Why he regrets not having mentors early in his career
• How he stays current with fast-moving research without drowning in information
• The puzzle at the heart of The Power of Regret—why an emotion that feels terrible is so universal
• Why “no regrets” culture is misguided, and how to confront regrets productively
• The difference between regrets of action and inaction—and why inaction regrets dominate as we age
• The four universal categories of regret: foundation, boldness, moral, and connection
• What 26,000 submissions to the World Regret Survey reveal about being human
• How to deal with regrets through self-compassion, writing, and sense-making
• The regret optimization framework, and how to apply it to the decisions that matter most
• Why kindness and pro-social behavior should become our “default setting”
• How changing the delivery of ideas matters as much as the ideas themselves in an age of AI and distraction