S4-EP16: Bestselling Author Dan Pink on the Power of Regret at any Age

May 6, 2022


Debbie talks with New York Times bestselling author Dan Pink about his new book: The Power of Regret. She wonders if “regret” is more common after midlife when you look back at the things you DIDN’T do.



Debbie talks with five-time New York Times bestselling author Dan Pink about his latest book: The Power of Regret: How Looking Backward Moves Us Forward. His books have been translated into 42 languages and have sold millions of copies around the world. 

She met Dan many years ago when she lived in DC and has been a fan ever since she read his first book, Free Agent Nation. That book was one of the first to legitimize solopreneurs and to predict the revolution in the workplace.

The premise of his new book is that while many people (especially Americans) proclaim “I have no regrets!” that statement is wrongheaded and, as Dan delights in pointing out, simply not true. 

We all have regrets and regret is a valuable emotion that can lead us to better understand ourselves and even to live our lives differently.

The book is partially based on the results of Dan’s World Regret Survey. He read through 15,000 replies from 100+ countries and deduced that there are really only four core regrets.

  • Foundational (If only I’d done the work… )
  • Boldness (If only I’d taken the chance… )
  • Moral (If only I’d done the right thing… )
  • Connection (If only I’d reached out… )

Debbie went into this episode thinking that “regret” has a special resonance for those past midlife who may be reflecting on what lies behind them – or what DOESN’T lie behind them – because they didn’t do it.

But Dan is pretty clear that regretting an inaction – what he defines as a Boldness regret – can come at any age. And that it’s never too late to do something about it.

Debbie reveals one of her biggest regrets to Dan and he offers some on-air therapy for how she should deal with it.

They also talk about Dan’s “failure resumé” and what he learned from it.

Be sure to pick up your own copy of Dan’s book (it’s a great read) to learn more about self-disclosing, self-compassion, and self-distancing when it comes to your own regrets; when to “undo” something you did in the past; and the importance of maintaining connections with friends.

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Thanks to our media partners

Encore.org, our newest media partner, is an ideas and innovation hub tapping the talent of those 50+ as a force for good. Founder and CEO Marc Freedman is an award-winning social entrepreneur and author, most recently, of How to Live Forever: The Enduring Power of Connecting the Generations. Looking for a great gap-year transition program? Check out Encore Fellowships, which match skilled, seasoned professionals with social-sector organizations in high-impact, paid assignments.


Modern Elder Academy is a program dedicated to navigating mid-life transitions. MEA, based in Baja California, Mexico, provides the place and the tools to start reframing your lifetime of experience. Grow whole, not old. Founder Chip Conley is a New York Times bestselling author, award-winning hospitality entrepreneur and a rock star of the mid-life transition movement. His newest book is Wisdom @ Work: the Making of a Modern Elder.


Next For Me is an important new resource for the 50+ crowd focused on rewriting life. Taking a gap year or timeout may be the best way to figure out "what's next" when you're in this stage of life. Founder Jeff Tidwell explains, Next For Me "connects and inspires our generation to evolve our post-50 lives through new work, a new purpose, or a new social contribution."