What You Can Learn From Regret (Karin Hurt Interviews Dan Pink)

What you can learn from regret: how to encourage boldness on your team

I caught up with Dan Pink, author of The Power of Regret, just after his fantastic keynote at the HR SHRM Virginia Conference on a special episode of Asking for a Friend. We dove into how his research on what we can learn from regret intersects with our Courageous Cultures work—and wow, there’s so much to take away.

Dan’s global research, collecting 20,000 regrets, revealed four common categories of regret. The one that hit home for me—and maybe for you too—is the regret of boldness.

You’ve heard these words before:

“If only I’d taken the chance.”

“I wish I had started that company.”

“If only I’d spoken up.”

These boldness regrets sting because they represent opportunities lost. And while personal regret is natural, here’s the kicker—organizations can create environments that minimize these regrets. It’s not all on individuals. You, as a leader, can build a culture where boldness thrives and regrets diminish.

How? It starts in everyday moments of leadership.

When someone disagrees with you, thank them for speaking up.
When someone makes a small mistake, celebrate it as a learning opportunity.
You won’t regret it.

And here’s the truth: Teams that feel safe to be bold give their best ideas, their most authentic selves, and their full capacity. Isn’t that what every leader dreams of?

Organizations that provide psychological safety will reduce “boldness regrets” and get greater capacity out of their team.

Memorable Insights From The Power of Regret

• “Regret makes us human, regret makes us better.”
• “By making us feel worse today, regret makes us better tomorrow.”
• “Understanding its effects hones our decisions, boosts our performance, and bestows a deeper sense of meaning.”
• “The lesson of closed doors is to do better next time. The lesson of open doors is to do better now.”
• “We regret foregone opportunities more than unfulfilled obligations.”

Other Voices on Learning From Regret

• “If only. Those must be the saddest two words in the world.” – Mercedes Lackey
• “Spend time with those you love. One of these days you will say either, I wish I had, or I’m glad I did.” – Zig Ziglar
• “Life is too short, time is too precious, and the stakes too high to dwell on what might have been.” – Hillary Clinton
• “I would rather regret the things I have done than the things I have not.” – Lucille Ball

Now It’s Your Turn.

What boldness regrets haunt you?
What’s one action you can take today to ensure your future self has fewer regrets?
And how are you leading your team to learn from regret and choose courage?

Encourage boldness, build psychological safety, and help your team learn from regret. It’s one of the most powerful gifts you can give.

Your turn.

What regrets do you have? What can you do about it now? Are you leading people who may have regrets? How can you help them learn from regret? How do you encourage your team to be more bold?