• Dan Connors

The Power of Regrets- find happiness by doing the opposite of what you most regret.

Updated: May 2


The Power of Regret: How Looking Backward Moves Us Forward

Daniel H. Pink 2022


We've all done things in life that we'd rather not think about anymore. We've all made mistakes, hurt someone, made bad choices, and somehow moved on to better things. But what's the proper way to deal with those past snafus? Ignore them and get a "No Regrets" tattoo on your butt? Or dwell on them and become convinced that you're an irredeemably bad person? There is a third option that's the topic of this great book by Dan Pink on regrets.


Pink has taken on the idea of regret and begun the most extensive look at what we regret and why with his World Regret Survey, a database of over 10,000 people from 105 countries. Pink looks at what people regret, tries to categorize the main ones, and looks for ways that these regrets can teach us all about what mistakes to avoid and what lessons to take from them. Dan Pink is a popular author of six best-selling books (all of which I have read), including Drive, A Whole New Mind, and To Sell is Human, each of which looks at the human condition and what makes us tick.


Pinks main thesis is that regrets matter- you just can't brush them off, and neither can you let them consume you. Regret is one of the most common negative emotions, and as other authors have noted, negative emotions provide valuable feedback from the world that something is not right. (Read Brene Brown's Atlas of the Heart for more on that). Regrets make us human and can be one of the most valuable emotions based on the information that it can provide us.


There are two different ways of dealing with disappointment when comparing yourself to others. You can look at those more successful than you and think, "If only I'd done X, Y, or Z, I could have been where they are." Or you can look at those below you and think "At least I didn't screw up like those people." Silver medalists in the Olympics are typically much less happy than Bronze medalists because they regret missing out on the gold medal, while the 3rd place finishers are excited to get any medal at all. Neither of these attitudes necessarily improves future performance, however.


Regret improves what Pink calls decision hygiene. Unpleasant emotions have a way of getting our attention, because we don't like experiencing them. Looking back at mistakes and regrets can actually boost future performance because that inspires us to do better. People who can sit with their failures and learn from them become more motivated to avoid them in the future. The ability to stay with these feelings deepens our understanding of our abilities and purpose. The question should always be- what is my regret trying to tell me about this situation? What can I learn from it? The "no regrets" crowd bypasses this crucial step and eventually ends up repeating the same mistakes over and over.


Pink goes over the many other surveys on regret that preceded his own. Not finishing education is one of the big ones, followed by botched romantic relationships, money mistakes, family problems, career choices, and parenting fails. He boils it all down to four core categories of regrets that he devotes entire chapter to.


1- Foundation regrets. The failure to be responsible, careful, and take care of yourself. Eating, drinking, smoking, and other destructive addictions dominate this category. People, especially in their youth, fail to plan for the future and neglect the basics of taking care of one's self. Temporal discounting is the cognitive bias that lets us overvalue the experiences of the now while ignoring the consequences for the future. This type of regret gradually creeps up on people as the behavior becomes more consequential. The only way to learn from it is to take a hard look at yourself and how your earlier choices got you to this point. Foundation regrets can be repaired, but only with honest hard work such as the 12-step program, counseling, or diet and exercise plans.


2- Boldness regrets. Because we are social creatures, we often choose not to speak up when we think that those words will cause disruption. Because we value stability, we often choose to stay with the safe and predictable jobs, spouses, and paths even when our heart cries out to take a risk and try something new. We experience boldness regrets for the path not taken, and it is a hard regret to live with. Sometimes our brain does us a favor by talking us out of a foolish choice, but other times it stunts our growth by scaring us into the status quo. We as humans have a built in need for growth, and the repeated failure to address that need leads to quiet, debilitating boldness regrets. The only way around these is to take those steps when opportunities arise, even if they are baby steps. The tiniest changes towards growth have a way of building on each other and leading to new understandings and abilities.


3- Moral regrets. This is your conscience talking to you. People feel guilt or shame about hurting others in the past. They may have made selfish choices that harmed others, or made deliberately aggressive decisions that they now regret. We all want to feel like we are at heart a good person, but that is hard to do when moral regrets keep reminding us that we were jerks to people in the past. The best way past these regrets is to try to repair the damage and make amends with the persons that were hurt. And if those people aren't around anymore, find someone else to do a good deed for and do your best to reverse the curse that holds you back.


4- Connection regrets. The largest category of regrets revolves around the people that we lose touch with. Sometimes the disconnect is sudden and intense, as a fight over something boils over and destroys an entire relationship. Other times the people just stop seeing each other gradually, and regret shows up when the memories come back. Connection regrets are strongest among family members, ex-lovers, and childhood friends. One big problem with these type of regrets is that any attempt at re-connection is likely to be awkward or difficult. Old arguments could resurface, and the emotional honesty required for a re-connection request is hard to come by. So instead of seeking old connections out, we stalk them on Facebook or ask others about how they are doing. And in many instances, the regrets run both ways- the other person ends up feeling the same way- missing you but afraid to make the awkward steps at approaching you out of the blue. Pink points to the Harvard study of longevity that showed connection in old age to be the number one determinant of physical and mental health as we get older.


The great information that we get from negative emotions is "Ouch. That hurt. Don't do that again." Regret is valuable data from our past that shows the things we did that need improvement. The stronger the regret- the greater the need for reflection and adjustment. By doing a worldwide survey of regrets, Pink says we now have a blueprint for a better life. By looking closely at the four main regrets- Foundation, Boldness, Moral, and Connection, we can look ahead and try better to avoid those pitfalls before they ever happen. Being human, we can't be perfect in that regard, but recognizing the core regrets as soon as we feel them gives us the information we need to take corrective action.


Pink finishes the book with advice on how to combat and process all of our regrets. Two of my favorite tools included self-compassion and self-distancing. Self-compassion gives us the ability to look at the pain and forgive ourselves for our all-too-human mistakes. Constant judgment gets us nowhere if it paralyzes us into inaction. Self-distancing gives us the power to look at the mistakes from a neutral place and see them more clearly. Being objective about regrets is hard because our defensive mechanisms take over and try to excuse away everything. But looking at the regrets as if someone else had done things wrong gives us the distance we need to take corrective action.


Humans are not that good at anticipating regrets or dealing with them. Some regrets are major and some are trivial. The four core regrets require our attention and time. Any regrets that fall out of those categories are more likely to belong to perfectionism, and it's best to "satisfice" when those regrets come up and not focus on them as much to save energy for the big stuff.


For more on this topic, I also recommend Bronnie Ware's Top Five Regrets of the Dying, taken from a hospice nurses actual experiences with dying people and how they'd wished their lives had turned out. I also recommend checking out the World Regret Survey and seeing they types of stories that people told Pink about their biggest regrets. I post a few of them below.


Female, Age 52

I regret not having more confidence in myself when I was younger to make better decisions. I still love who I am today, but I wish I'd taken more risks when I was younger.


Male, Age 32

I wish I would have recognized that I was an alcoholic well before I ruined relationships...friendships, romantic relationships, family, business. I wish I would have figured out sooner...then I would not have cheated on my girlfriend and put mine and other's lives at risk since I drove drunk nearly every day for YEARS.


Female, Age 46

I regret that after I divorced, I chose another partner who had a temper and turned out to be horrible to my children. I regret that I stayed with him for so long thinking that I could "mediate" every conflict and keep everyone happy. My children suffered during a large portion of their childhood because of my choice and my conflict aversion.


Female, Age 53

I regret cheating on my husband more than once to make me feel better about myself in the moment. In doing so, made me feel worse to the point of self sabotaging who I am and my health.


Male, Age 30

I prioritized stability and gainful employment over following my partner on her exciting move out west. I lost both my partner and my new job within six months.


Female, Age 35

Not following the riskier path.


Nonbinary, Age 21

I was often rude to people. Once brought a cousin to tears, saying that she was lucky to lose her father, because now the state pays her maintenance. I once told my grandmother that I would not want to have a mother like her. And now I'm ashamed to remind them of this and ask for forgiveness.

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