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

Alex Soojung-Kim Pang is a historian, futurist, and one of the most compelling voices rethinking the way we work, rest, and create. He is the author of Rest, Shorter, and The Distraction Addiction—books that have reshaped the global conversation on productivity and wellbeing.

Alex has worked across academia, tech, publishing, and firms like the 4 Day Week Gobal. Today, he leads programs with 4.dk - a Dutch team leading 4-day week experiments in Denmark, and 4 Day Week studio.

In this episode, Alex and Subbu explore the science and art of deliberate rest, why overwork is counterproductive, and how the four-day week is moving from radical idea to mainstream practice. The conversation draws on history, neuroscience, and real-world experiments to reveal how we can all work better by working less.

We cover:

• Alex’s unconventional “Grand Theft Auto” career path—from historian to tech futurist to rest evangelist
• The mentors and moments that shaped his thinking
• Why overwork persists—and how it erodes creativity, judgment, and empathy
• What it really takes to rest well: active recovery, multiple time scales, and deliberate planning
• The “four-hour rule” of deep work and how great minds from Darwin to Hemingway structured their days
• The link between morning routines, the default mode network, and creativity
• The concept of deep play and why serious hobbies sustain high performance
• The business case for the four-day week, and what early adopters have learned
• How AI is changing the way we discover and apply research
• What the music industry can teach us about creativity and collaboration in the age of automation

Michael Morris is the Chavkin-Chang Professor of Leadership at Columbia Business School, and one of the world’s leading scholars at the intersection of culture, cognition, and leadership. A cultural psychologist by training, his research has shaped how we understand identity, influence, and the psychology of change across global contexts. Over a career spanning decades, Prof. Morris has published over 200 academic papers and founded Columbia’s Leadership Lab and Behavioral Lab.

In this episode, Prof. Morris and Subbu unpack the deep instincts that shape our collective lives—from the psychology of sports teams to corporate leadership—and why culture is not fixed, but dynamic, contested, and constantly evolving.

To listen to the full episode, go here: bit.ly/m/cult_m

We cover:

- Prof. Morris' journey from literature and cognitive science to pioneering cultural psychology

- The origin story of the field—and why it had to reemerge after being sidelined for decades

- Why culture is not what people say, but what people signal

- What South Korea’s 2002 World Cup team taught us about identity and adaptability

- Peer, hero, and ancestor instincts—and how they shape organizational behavior

- What leaders often get wrong about culture change

- Why the legitimacy of the messenger matters more than the message

- How companies like Infosys, HCL, and GM shifted culture through surprising signals

- The future of cultural analysis in an age of AI and big data