Respect for Regret

The Nobel family was full of tinkerers and experimenters. Alfred’s father spent his life building infrastructure for roads and railways. As Alfred became an adult he worked with his father to explore more efficient ways to blast rocks which were obstacles in the way of roads being built. In short, Alfred became a titan of TNT which had an explosive history. He’s credited with being the discoverer of dynamite which became a safer way to blow things up. Another brother, Ludvig,  was an experimenter and entrepreneur in his own right. Ludvig established himself as a captain of the oil industry. In time, Ludvig passed away and Alfred found himself reading what was supposed to be his brother’s obituary in a newspaper. Legend has it that the newspaper had misprinted Ludvig’s biography and replaced it with that of Alfred. Alfred was basically reading an obituary of himself written by a journalist. The obituary wasn’t kind. It emphasized the pain and misery that Alfred’s life work had inflicted on others. It focused on the destructive and dangerous elements of dynamite and all of the loss it had imposed on people including the death of another of Alfred’s brothers. Alfred soaked this message in and determined that when his actual time came he wouldn’t be known for the damage dynamite did but for benefits his efforts had offered. Alfred lived for a few more years and when he passed away, his estate surprised many by not distributing his accumulated wealth to his family but overwhelmingly it was directed to a series of awards that would be offered to scientists and other intellectuals that were doing work for the benefit of humanity. So, the story goes, came to be the beginnings of the lauded Nobel Prizes.

Daniel Pink offers Alfred Nobel’s story in his recently released book, The Power of Regret. Pink introduces the Nobel story as one which reflects a value of regret. Feeling bad about things isn’t always a negative. It can constructively serve to motivate and direct our energies to taking steps to improve things. Alfred, by reading the incorrect obituary, felt regret looking back on some of his life’s work and used it as motivation to make a meaningful difference going forward. As Pink’s subtitle suggests and Nobel’s example offers, regret offers an example of “How looking backward moves us forward.” In our last note, I offered a personal regret that has spurred personal changes which have led to a better use of time. In this note, I’ll offer a summary of Pink’s framework for regret which can be the basis of looking back both personally and in business in order to improve our futures.

Pink’s premise is that the cultural backdrop suggesting regret is something from which we should recoil is flawed. A life of “no regrets” isn’t just unreasonable, it’s unhelpful. To be human is to make mistakes. To make mistakes is to end up with regret. If we didn’t regret our miscues and mishaps, we would be incapable of learning and improving our futures. Pink notes of regret, “It clarifies. It instructs. Done right, it needn’t drag us down; it can lift us up.”

As a definition for regret, Pink offers “the unpleasant feeling associated with some action or inaction a person has taken which has led to a state of affairs that he or she wishes were different.” Negative emotions aren’t things from which we need to retreat. We should engage these emotions and use them to spur thinking about what caused them. Perhaps, we can then reflect on the past in order to improve the future. The upside of regret suggested by Pink is that it may help us to internalize that our past choices have led us to where we are. If we want a better future destination, it isn’t destined by past choices, but those we make now today. We can improve our futures independent from our past.

Pink’s findings follow research done by the American Regret Project. Pink collaborated with researchers to collect information from over 4,000 North Americans via surveys and interviews. Participants were asked questions like “How often do you look back on your life and wish you had done things differently?” From the massive amount of information collected, four categories of regrets were distilled.


Foundation regrets follow lapses in self-control. These are regrets of not taking care of ourselves. It can include physical, mental, health, or financial neglect. Where we overvalue the present and ignore the future, when we inevitably arrive in the future, we do so in a worse state. In our new present we feel regret for the squandered opportunity we had in the past. We wish we would have done things to deliver ourselves into the future better prepared. Foundation regrets tend to include words like “if only” or “I really should have done…” or “too much” or “too little.” Foundation regrets are breakdowns in self-discipline. They reflect abdication of responsibility and mis-managing moderation. Foundation regrets are what Aesop’s Fable of the Ant and the Grasshopper is all about. Too much pleasure and too little planning leads to a tougher tomorrow full of foundation regret. The common areas of foundation regret involve squandered or missed educational opportunities, mismanaged personal finances, and a failure to take care of one’s physical health.

Foundation regrets are found more in older people because it takes time for them to materialize. When we’re having a good time today, we aren’t feeling the pain of these decisions for decades. It’s the passage of time that reveals these regrets slowly. The intensity of pain associated with foundational regret depends on how much time we have left to make positive changes. The less time, the more pain. This form of regret isn’t just about not taking care of oneself but can also include feeling bad about not having lived up to one’s potential. We feel regret where we recognize that we’re on some level responsible for where we find ourselves. If we aren’t responsible, then it’s not regret, but disappointment that’s felt. The good news about recognizing our responsibility is that we can do something to resolve. Pink offers the Chinese proverb of “The best time to plant a tree is twenty years ago. The second-best time is today,” as a recommended response to foundation regrets. We can’t fix the past, but we can influence today. Take action today to create a better tomorrow.

We can look at things like hangovers, indigestion, and receiving our credit card statements as opportunities to connect our recent actions with results. We don’t have to wait decades to see the deep deterioration of poor choices. If we’re able to reflect on the suffering of a headache from a hangover as being connected with poor choices the night before, we can use this to question our relationship with alcohol. So, too, it is with credit card statements. We can check ourselves before we wreck ourselves. Learn that our choices do have impacts. These impacts only deepen the longer we let these poor choices repeat.

“All deep structure regrets reveal a need and yield a lesson. With foundation regrets, the human need it lays bare is stability: we all require a basic infrastructure of educational, financial, and physical well-being that reduces psychological uncertainty and frees time and mental energy to pursue opportunity and meaning. The lesson reaches back two and a half millennia. Think ahead. Do the work. Start now. Help yourself and others to become the ant.”


Boldness regrets flow from missed opportunities. We look back on our lives and wonder about the things we didn’t do. We yearn for the chance to go back and take risks we were too afraid to face. Boldness regrets include words like “if only” or “what might have been” or “what if.” Sometimes this regret is about actions taken. We regret starting that business that failed, for example. However, most boldness regret revolves around the things we didn’t do. We face many choices in life. In each of these lies a decision between daring and dodging, between taking a chance or playing it safe, or between challenge and comfort. Where we opt for safety or avoidance, we’re likely to feel boldness regret down the road. Pink suggests that “at the heart of all boldness regrets is the thwarted possibility of growth.” Where we fail to act, our future selves tell a story that suggests we have missed out on a positive outcome. Boldness regret mirrors closely the number one regret of the dying identified by palliative care nurse, Bronnie Ware. She observed that those nearing the end of their lives regretted most not living a life of authenticity. They regret not being true to themselves. This reflects a form of boldness regret.

“All deep structure regrets reveal a need and yield a lesson. With boldness regrets, the human need is growth—to expand as a person, to enjoy the richness of the world, to experience more than an ordinary life. The lesson is plain: Speak up.”


Moral regrets are about whether we’ve compromised on an area that we hold in high regard. Do we have principles? Did we violate them? When we hold something dear and in the moment act inconsistently with it (or fail to act) what’s clear is that regret will be in our future. Where we have violated a value, we feel moral regret. The good news is that Pink’s research found this to be the smallest category of regret. The bad news is that these types of regret produced the most pain. Pink notes, “Moral regrets sound like this: If only I’d done the right thing.” Pink’s research suggests that our views on morality tend to gather around five categories: care, fairness, loyalty, authority, and desecration. These groups share commonalities with what Pink offers as “The five regretted sins. Deceit. Infidelity. Theft. Betrayal. Sacrilege.

Moral regrets around care flow from hurting others for no reason. Bullying is an example of this type of moral regret. Most of these types of regrets impose needless hurt on others through verbal attacks and less so physical. Follies of fairness follow from taking advantage of someone else. Loyalty is about preserving trust. Where we breach trust by being disloyal, moral regret surfaces. These types of regret can result from infidelity or cheating. Subjugating personal interest to that of a group is important for our need to belong and benefit from the safety a group provides. Where we undermine the authority of a group, moral regret can be created. Finally, desecration involves violating a form of sacrilege. A core principle is ignored.

Whereas most boldness regrets result from not doing something, most moral regret is the result of doing something of which we’re not proud. Moral regret can result from not acting. For example, being a bystander to bullying. However, moral regret from doing something “bad” is more frequent than doing nothing. There’s a lot of agreement around what moral behavior looks like across demographics. Independent of age, culture, and background, most tend to see hurting innocent people, lying, cheating, and stealing as wrong.

Pink offers a benefit from moral regret writing, “There is something heartening about grown women and men waking up at night despairing over incidents decades earlier in their lives in which they hurt others, acted unfairly, or compromised the values of their community. It suggests that stamped somewhere in our DNA and buried deep in our souls is the desire to be good.” We want to be good. Where we aren’t we feel bad. The lesson moral regret teaches is that doing good is good for us.


In the surveys conducted, connection regrets were the largest category. They involve pain associated with relationships that have separated either by action or inaction. Relationships with family, friends, and colleagues can all be impacted. The commonality is that a relationship that was somewhat satisfactory was in place that for some reason is no longer. As the pain of the relationship builds, regret is formed by the recognition that we played some role in the failure of the friendship. If the other person is still around, the connection regret remains “open.” We have some opportunity to still do something about it yet remain scared of the emotional uncertainty associated with reaching out. If we no longer know where the other person is or they’ve passed away, the connection regret is “closed.” This brings separate pain.

Pink observes that, “connection regrets sound like this: If only I’d reached out.” Pink suggests that connection regrets can be especially painful as they are the result of a breakdown in our ability to achieve our deep seeded desire to belong.

Pink presents two classes of connection regret: rifts and drifts. Rifts are active disagreements. Some kind of fight breaks out which disrupts the relationship. It can be consequential, like a betrayal, or it can be trivial. In either case, one or both parties is offended enough to break off the relationship in the moment. Drifts involve a deterioration in a relationship that follows from inactivity. The end of the relationship isn’t a clear event like in a rift. It’s not making contact and slowly losing contact. It can take years for those in a relationship to realize its been lost due to drift. Drifts tend to be more common than rifts.

How Regret Serves

Pink suggests the strength of regret is that it offers the inverse of an ideal existence. Knowing what we don’t want helps point us in the direction of what we do. This lesson is at the heart of the work of nurse Bronnie Ware noted earlier. There are several parallels to the regrets Ware identified and those that are quite prevalent in Pink’s research with the American Regret Project. In both cases, the utility of regret is that it points us away from where we don’t want to go and helps us see where a better direction may be. Pink writes, “If we know what we truly regret, we know what we truly value.” Looking, listening, and learning from our own experiences as well as those of others helps us see that regret clarifies things we don’t want to do. It shows us how not to behave.

Working to use regret to make your life better is learning to tell better stories to yourself. We’re both the creator and the character. Yes, some of the plot has played out, yet we’re still the creator that can influence the direction of the rest of our story. We can let regret detail a direction that takes us down exploring ways of how things could have been better “if only.” If only stories heighten the hurt of regret and keeps us kicking ourselves. However, we can use regret to reframe the past and see that even if things could have been better but they also could have been worse. If we tell ourselves stories about our past where we’re grateful that “at least” things didn’t go as poorly as they could, we can see our past positively. One story serves, the other stings. In either case, the story is ours to tell. Taking the time to listen to our regret and lean into it improves decision making. Pink suggests because the pain imposes a pause, the pause allows us to collect information and consider improvements for future activity. Additionally, reflecting on our regrets has been shown to promote persistence.

Typically, regret is pain following from reflecting on the past. However, we can consider anticipating regret as a tactic to improve our actions today. As a factor in our decisions we can try to project ourselves into the future and wonder what our future self may think of a decision we make. Will they be happy? Will they look back and see the time and effort we took to make a better decision with respect? Or, will they look back at what we’re about to do with regret? Pink writes, “Anticipating our regrets slows our thinking. It applies our cerebral brakes, giving us time to gather additional information and to reflect before we decide what to do. Anticipated regret is particularly useful in overcoming regrets of inaction.” Again, if our decision involves an area that may involve one of our four categories, we should work to anticipate regret to aid making a choice.

As we begin to see the value in regret we can develop our awareness and use Pink’s categories of regret to further reflect. When we identify a regret, we want to, first, determine whether the regret is the result of something we did or didn’t do. If it’s something we did, there are a few things we can do to minimize the effect of the action to reduce regret. In some cases the action may be reversible. We can work to undo what was done. If we can’t fully undo, perhaps, we can at least apologize or offer a form of restitution. Barring these options, Pink suggests we look at our past actions and search for the silver lining. Are there other ways we could have made things worse? Can we explore “at least” options? At least we didn’t do x. Sharing our past pains with others can also reduce feelings of regret. By reliving the regret we relieve the pressure of its pain. Knowing that we’re human and as a result mistakes are inevitable may soften the sting of our past mishaps. Finally, analyze the event so that you learn the lesson and reduce repeat occurrences. Use your regret (and that of others) to become conscious in the moment making better decisions ensuring that future regret will be less. Consider choices in the present against the four regret types. Are you making a decision in one of these areas? If so, take your time to get things right. Regret helps us alter our behavior so that we can avoid worrying about what might have been down the road.

Here’s a link to a separate BBC article discussing Pink’s book. If we’re warming up to the wealth of value that may be waiting for us in our regrets, consider whether there may be regrets related to business decisions. Are there decisions we’ve made as an organization that we regret? Are we taking time to reflect on decisions to learn from them? If there are decisions we’ve made in the past that didn’t work at well, can we review them and categorize into one of the four groups of regret? Knowing then what we know now, how would we do things differently? Can we use this exercise to make better decisions in the future?