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Blog Short #153: How to Deal With Regret

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Everyone experiences regret even if they say they don’t. You might believe that everything you’ve experienced has gotten you to where you are today and that you wouldn’t have done anything differently, yet you’ve still experienced moments of regret along the way.

To have no regrets would mean having no conscience or being perfect and above making errors. We’ve all done something or not done something that we regret.

Regret is a teacher and keeps you on track. It’s valuable. It “clarifies” and “instructs, and when used correctly, can lift you (Pink, 2022).

Today, we’re going through Daniel Pink’s four “core regrets,” as outlined in his book The Power of Regret, along with a quick sketch of the strategies he offers to deal with them. (See note below).

Regret is Built into Our Cognitive Structure

We have regrets because of our ability to “dip back into the past, rewrite history, and imagine” what would have been better (Pink, 2022). By comparing where we are with where we could have been if only we’d acted differently, we can construct a future we could have had in our minds. Pink calls this “counterfactual thinking.”

He also points out that we blame ourselves 95% of the time for our regrets based on faulty decisions.

How Regrets Can Help Us

Pink points to three benefits you can take advantage of when you have a regret.

  1. Improve decisions. Regrets make you rethink your behavior and decisions. They slow you down and require more research and consideration about what you’re doing and the direction you’re taking. Although regret feels negative, the benefits are positive.
  2. Boost performance. When you have to think about alternative scenarios – what might have been – you widen your vision. You consider new ideas and possibilities. You stretch yourself, develop creative strategies and solutions, and forge new pathways. Your performance improves as a result.
  3. Deepen meaning. Comparing your “if onlys” to what could have been adds more poignancy to your experiences and supplies meaning. You can come up with silver linings, which Pink calls “at leasts.”

Regrets are broader than failures. They’re part of a process of being and doing and provide guidance along the way. They can come from either actions or inactions.

Pink categorizes them into “four core types.” You’ll recognize all of them.

The Four Core Regrets

1. Foundation Regrets

Foundation regrets are about “failure to be responsible, conscientious, or prudent.”

These regrets are about basic life stability: home, job, money, and health. Think of it as your personal infrastructure. When you overspend, indulge in unhealthy habits, procrastinate, or fail to fulfill your responsibilities, the foundation underneath you wobbles. And if you continue, it can develop cracks and fissures that make life unsafe or untenable.

Foundation regrets come from ignoring how current habits and behavior will negatively impact your future well-being.

2. Boldness Regrets

Boldness regrets are about the “opportunities you didn’t take.”

These are regrets of inaction. You didn’t take that trip to Europe, open that business, or ask that girl to go out. These are the regrets of what might have been if only you’d been brave enough to take the risk.

3. Moral Regrets

Moral regrets are about doing something that rubs up against your values and conscience.

This category is harder to define because of the variability of what people consider right or wrong. Much of what we agree upon comes from Judeo-Christian ethics outlined most succinctly by the Ten Commandments, but even there, interpretations vary.

Pink outlines five generally regretted actions which are:

  1. Causing harm
  2. Cheating
  3. Disloyalty
  4. Subversion
  5. Desecration

Moral regrets are about “doing the right thing.”

4. Connection Regrets

Connection regrets are about failure to attend to the people who give your life meaning and purpose.

These are partners, spouses, parents, children, siblings, friends, and colleagues. You have regrets either about a relationship that’s no longer intact or one that’s fractured and in danger of disintegration. Pink calls them “closed-door” or “open-door” relationships.

Connections regrets are the largest of the four categories.

The Strategies

Undo it.

This strategy asks the question, “What can I do to make amends or repair?” Several weeks ago, we covered how to apologize. Sincere apologies are a mainstay of this strategy.

You can apply this strategy to someone else or to yourself. When applied to you, you’re usually working on foundation issues – habits devoted to keeping up with things and taking care of yourself. When applied to someone else, it may be either a moral or connection regret.

At Least it.

At Leasts look for the upside of regret. Pink provides three questions to ask yourself to use this strategy:

  1. “How could the decision I now regret have turned out worse?”
  2. “What is one silver lining in this regret?”
  3. “How would I complete the following sentence? “At least . . .”

An example of an “at least” statement is: “I regret my first marriage, but at least I got my children, for which I am forever grateful.”


Studies have shown that telling someone else about regrets is relieving.

Regrets take an unspoken toll on you and lead to chronic rumination. They’re taxing emotionally and physically and can drain you of energy.

Even writing them out or speaking them into a recorder is helpful.

By doing any of these, you relive the situation, followed by feelings of relief. Plus, putting something into words or writing it forces you to crystallize and integrate your thoughts so you can see them objectively.

If you’re not comfortable telling someone, use writing or recording. Pink suggests writing for 15 minutes three consecutive days or talking into a voice recorder for 15 minutes three successive days.


Gaining some distance from the regret allows you to see it without beating yourself up. You “zoom out” and act as an observer detached from the situation. There are three ways to do this:

  1. Act as a “fly-on-the-wall,” and listen to yourself telling someone else what you regret.
  2. Go five or ten years out (or longer) and imagine how you would feel about the regret at that point.
  3. Use third-person words like “she, him, or they” when describing the regret rather than first-person words like “I, me, or my.” You could also refer to yourself as “you,” which gives you some distance.


Self-compassion is an alternative to self-criticism. It’s been studied extensively by psychologist Kristin Neff. Taking from her research, Pink describes it like this:

Rather than belittling or berating ourselves during moments of frustration and failure, we’re better off extending ourselves the same warmth and understanding we’d offer another person. Self-compassion begins by replacing searing judgment with basic kindness. It doesn’t ignore our screwups or neglect our weaknesses. It simply recognizes that “being imperfect, making mistakes, and encountering life difficulties is part of the shared human experience.” (Neff, 2007).

The biggest worry people have about self-compassion is that they think it’s permissive and complacent and encourages people to ignore their responsibility, but this isn’t accurate. It keeps us from ripping ourselves to shreds while also turning our attention toward making amends, finding solutions, and being responsible.

Beating ourselves up keeps us immobile because it entraps us in a circle of shame rather than allowing us to accept our mistake, neutralize it, and take action.

Anticipating Regrets

We’ve been talking about regrets for things that have already occurred. You can also use the information you’ve learned today to prevent regrets by taking action now.

You can change the way you treat people, decide to take calculated risks when opportunities arise, look at your daily behavior and habits related to foundation responsibilities, and value your relationships by showing more appreciation and gratitude for the people in your life who inspire you, provide meaning, and give you purpose.

And, if you like this subject, read Daniel Pink’s book! It provides a whole different way of looking at regrets. It’s therapeutic!

That’s all for today.

Have a great week!

All my best,


A quick note: Daniel Pink and associates conducted a survey in 2021 called the American Regret Project that polled 4,489 people about their regrets, which is cited throughout his book. The survey is ongoing today. You can take the survey ​here​.


Neff, K. (2011). Self-Compassion: The Proven Power of Being Kind to Yourself. HarperCollins, Kindle Edition.

Neff, K. D., Kirkpatrick, K. L., &  Rude, S. S. (2007). Self-compassion and adaptive psychological functioning. Journal of Research in Personality 41(1), 139–54.

Pink, D. H. (2022).  The Power of Regret: How Looing Back Moves Us Forward. Riverhead Books.

Zeelenberg, M., & Pieters, R. (2007). A theory of regret regulation 1.0. Journal of Consumer Psychology 17(1),  3–18.

Zhang, J. W., & Chen, S. (2016). Self-compassion promotes personal improvement from regret experiences via acceptance. Personality and Social Psychology Bulletin 42(2), 244–58. DOI: 10.1177/0146167215623271

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