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The Power of Regret: Interview on Daniel Pink's New Book

New York Times bestselling author Daniel Pink on how to use regret to motivate


 Daniel Pink is a New York Times bestselling author and speaker on the subjects of motivation and business. In our interview on The Power of Regret: How Looking Backward Moves Us Forward he taught us how regret is a storytelling process that we can use to our advantage to better our lives. Sharing regrets can also be a tool for good leadership, building on qualities like trust and humility.

Take Amazon founder Jeff Bezos, for example. In the 1990s he was deciding whether to leave his job to start his company on the fledgling World Wide Web. He told an interviewer he imagined himself at age 80 regretting not having tried.

"I knew that would haunt me every day, and so, when I thought about it that way, it was an incredibly easy decision," he told Jessica Stillman of Inc.

Daniel Pink told Growth Faculty this type of regret is a “boldness regret.” Using psychology research and data from both his American Regret Project and his World Regret Survey, Daniel Pink discovered Four core categories of human regret.

1. Foundation regrets

These are regrets that rock our need for some level of stability. Regrets include failure to be responsible, conscientious, prudent.

"I should have selected different subjects and worked harder earlier in my life to obtain the compounding benefits throughout life." - Female, 46, Australia.

Lesson: Think ahead. Do the work. Start now.

2. Boldness regrets

We are much more likely to regret the chances we didn't take than the chances we did, especially as we age. Foregone opportunities to launch a business, chase a true love, or see the world.

"I regret not having the courage to be more bold earlier in my career and caring too much what other people thought of me," Female, 33, South Africa.

Lesson: Take action. Speak up. Ask him out. Take the trip. Start that business. Step off that train.

3. Moral regrets

These are decisions where we took the low road. Deceiving a spouse, cheating, swindling a business partner.

"I bullied a new kid in seventh grade. He was from Vietnam and hardly spoke any English. Horrible!" - Male, 52, USA.

Lesson: When in doubt, do the right thing.

4. Connection regrets

Connection regrets arise when we neglect the people who help establish our sense of wholeness. People give our lives purpose. 

"I wish I had tried harder to foster deeper relationships with my work colleagues. I've worked at the same place for over 30 years but I'm not sure I would really call any of the people I've worked with a close friend." - Male, 62, USA.

Lesson: Do better next time, or do something about it now. Make the call, make the visit, say what you feel. Push past the awkwardness and reach out.

Free Download: 10 Leadership Qualities That Will Help Solve Challenges in 2022


For Daniel Pink the power of regret comes from looking backward, and forward (to opportunities). "Think 'inward', outward', and ‘forward’,” he says. People should use regrets to their advantage by seeing them as a ‘reverse negative’ of the things they value most.

"If only I'd done the work" = a value of stability

"If only I'd taken the risk" = a value of growth

"If only I'd done the right thing" = a value of goodness

"If only I'd reached out" = a value of love

His Regret Optimisation Framework suggests ways we can take positive action to honour these values.

Daniel Pink’s Regret Optimisation Framework


  • Undo it. Apologise, make amends, try to repair the damage
  • "At Least" it. Find the silver lining: think about how the situation could have turned out worse and appreciate that "at least" it didn't.

For any regret (ACTION or INACTION)

  • Self-disclosure. Relive and relieve the regret by telling others about it - admission clears the air - or write about it in the privacy of a journal.
  • Self-compassion. Treat yourself as a friend.
  • Self-distancing. Zoom out in time, in space, or through language to analyse the lessons learned from the regret.

To use ANTICIPATED REGRETS in decision making

  • Satisfice on most decisions. If you are not dealing with one of the four core regrets (foundation, boldness, moral, compassion) then make a choice and move on.
  • Maximise on the most crucial decisions. If you are dealing with one of the four core regrets, project yourself into a point in the future and ask yourself which choice will most help you build a solid foundation, take a sensible risk, do the right thing or connect with others.


7 other techniques from Daniel Pink's book.

1. Start a regret circle where you join others to tell stories of regret and the group categorises each regret and works through a disclosure-compassion-distance process.

2. Create a failure CV or resume. This is a thorough inventory of our flops. View it as an observer to find patterns and avoid future mistakes.

3. Study self-compassion. Dan says few subjects have spoken to him as powerfully. He recommends Kristin Neff's website and book Self-Compassion.

4. Pair New Year's resolutions with Old Year's regrets. Look back on your year and list three regrets. Write them down, and make undoing the action regrets and transforming the inaction regrets your top resolutions for the New Year.

5. Mentally subtract positive events. To take the hurt and emotions out of a regret, think of all the decisions and mistakes that led to a happy situation. Then take the happy situation away. It casts regrets in a new light.

6. Participate in the World Regret Survey

7. Adopt a journey mindset. Sustain your behaviour after reaching goals or completing a task so you don't slack off and regret the lapse.

(For more team-building activity ideas that improve culture try these suggestions from Patrick Lencioni) 

Conversation points and Questions for teams:

·       What aspects of this interview on Daniel Pink’s book The Power of Regret resonated most with you?

·       Are you comfortable sharing a couple with your team? Self-disclosure, even to yourself, can help.  

·       Would you like to participate in the World Regret Survey (

·       Is there an action regret (something you did) that you can undo by apologising or making amends? Can you “at least” it by finding the silver lining?

·       Can you think of a situation where you are unsure of your next move? Ask yourself “In the future, will I/we regret this decision if I/we don’t do X?" Answer the question. Apply that answer to your current situation.

When deciding a course of action…

1.     Begin by asking whether you are dealing with one of the four core regrets: Foundation regrets, Boldness regrets, Moral regrets, Connection regrets. (If not, satisfice – make a choice and move on). The Regret Optimisation Framework can be found on page. 205 of The Power of Regret.

2.     If one of the big four, spend more time deliberating. Project yourself into the future (5 years, 10 years, age 80). From that vantage point ask yourself which choice will help you build your foundation, take a sensible risk, do the right thing, or maintain a meaningful connection? Anticipate these regrets. Then, choose the option that most reduces them.


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