Want to Live More Intentionally? Harness the Power of Regret

Last September, I wrote an article about how the book The Top Five Regrets of the Dying by palliative nurse Bronnie Ware provides a roadmap for a living a life with no regrets. Specifically, the top regrets that Ware discovered over her years of sitting at the bedsides of dying people included being true to oneself, prioritizing relationships over career, and allowing oneself to be happy.

Author Daniel H. Pink, known for his books including Drive and When, dove even deeper into the research of regret in his recent book The Power of Regret: How Moving Backward Moves Us Forward. Pink draws on regret research completed by others, as well his own. Specifically, Pink and his team completed the largest quantitative analysis of American attitudes on regret in 2020: the American Regret Project which included 4,489 people comprising a representative sample of Americans. In addition, he launched the World Regret Survey – which so far has been completed by more than 19,000 people in 105 countries.

Pink’s findings about how the desire to live with “no regrets” is harmful, and potentially even dangerous, gives us a wealth of knowledge about how the power of regret can be harnessed to allow us to live a more intentional, purpose-filled life.

(Almost) Everyone Has Regrets, But These Four are Core

Regret is a unique emotion in that it is created by looking at an action or inaction from the past, and comparing the actual outcome to a potentially different outcome had a difference choice been made. Pink explains that the “mental trapeze act” that regret requires – going between past and present, reality and imagination – is possible for everyone except for young children whose brains haven’t fully developed and adults with brain injuries or illnesses. In other words, “people without regrets aren’t paragons of psychological health. They are often people who are seriously ill.”

Between the American Regret Project and a sampling of the World Regret Survey, Pink found that four regrets are universal, spanning across life domains such as health, career, education, and relationships. He summarizes the four “core” regrets as follows:

Foundational Regrets: These are the regrets about not building a more stable foundation for our lives. This can include choices about how we spent our time, money, and energy in the past and whether they contributed to a solid – or flimsy- foundation. They sound like: If only I’d done the work.

Boldness Regrets: These are the regrets about the chances that we didn’t take, and the decision we made to play it safe instead. They sound like: If only I’d taken that risk.

Moral Regrets: These are the regrets about taking the “low road” rather than the high one. They sound like: If only I’d done the right thing.

Connection Regrets: These are regrets about the fractured or unrealized relationships with people in our lives (as Pink puts it: rifts and drifts). They sound like: If only I’d reached out.

These four core regrets provide a framework for learning about how regret impacts every area of our lives, while also showing us how we can learn from them. As Pink explains, “The four core regrets operate as a photographic negative of the good life. If we know what people regret the most, we can reverse that image to reveal what they value the most.”

“If Only” Regrets Are More Frequent, and Cause More Pain Than “At Leasts”

You may notice that the four core regrets all start with “If only…” This is an example of what is called counterfactual thinking (CFT) in psychology. When we think of something that occurred in the past, “at least” CFTs focuses on what could have been worse, while “if only” CFTs focus on what could have gone better.

For example, if you didn’t study for a test and got a C, you could tell yourself, “At least I got a C. I could have failed.” Or you could tell yourself, “If only I had studied harder, perhaps I could have earned an A.” “At leasts” provide some comfort, while “if onlys” cause despair.

The majority of people’s regrets – upwards of 80% according to some research – fall into the “if only” category. This may seem depressing, but it is actually where the power of regret can be harnessed. While “if onlys” make us feel worse in the short-term, they can help us do better in the future in a way that “at leasts” can’t. They can strengthen our decision-making skills, make us more persistent, and improve our future performance.

Regrets of Inaction Grow Over Time

It is not surprising that “if onlys” make up about 80% of people’s regrets, because in Pink’s American Regret Project survey, inaction regrets outnumbered action regrets by nearly two to one. This is consistent with other research by Thomas Gilovich and Victoria Medve which found that actions “generate more regret in the short term; but inactions, or errors of omission, produce more regret in the long run.”

While time may “heal all wounds”, it seems that it worsens inaction regrets. Gilovich and Medve asked participants about regrets over different time periods and found “when focused on the last week, the respondents were rather evenly split between those who most regretted their actions (53%) and those who most regretted their failures to act. However, when looking back over their entire lives, a substantial majority (84%) reported greater regret for what they failed to do.” Pink’s American Regret Project supports this finding – inaction regrets increase as people get older.

When it Comes to Regrets, Is the Door Open or Closed?

Out of all the four core regrets, Pink found that connection regrets were the largest among research and survey participants. This is certainly true for me, specifically drifting apart from friends that were once close. I could make excuses about having a full life with young children, but the truth is that I have harbored resentment about others not reaching out to me, when I could reach out to them just as easily.

The truth I often overlook is that I am lucky that the doors of these regrets as still “open.” The people that I have drifted away from are still alive. If I could get over feelings of resentment or fear of awkwardness, perhaps the relationship could be restored.

But what if an open door becomes a closed door? What if we fail to tell someone how much we care for them before they pass? What if awkwardness prevents us from connecting with an old friend and then tragedy strikes, closing the door forever? As Pink explains, “Both types of regrets nag at us, but for different reasons. Closed door regrets distress us because we can’t do anything about them. Open door regrets bother us because we can, though it requires effort.” Unfortunately, many of us are unwilling to make the effort to overcome awkwardness and end up holding onto these regrets for the rest of our lives.

Learn From Your Regrets, but Don’t Dwell on Them

Regret is an unpleasant emotion, why many of us choose not to think about them at all. But if we take the time to use regret as an instructional tool, how do we learn from them and then let go?

The trick is finding the delicate balance between assessing our regrets and not dwelling on them and creating a negative spiral. As Pink explains, “Repetitive thought can worsen regret, and regret can exacerbate repetitive thought, creating a descending spiral of pain.”

To avoid this pitfall, we need to have keen self-awareness, lots of self-compassion, and the ability to distance ourselves from the regret enough to derive its lessons. In other words, we can use regret to assess our behavior, but should never be used to judge our character.

Pink suggests several ways to assess and learn from our regrets, including creating a “failure résumé” and meeting with others in a “regret circle” – like a book club where you discuss and work through past regrets. But my favorite idea is doing a regret audit from the previous year, or what Pink calls “Old Year’s regrets” (as opposed to New Year’s resolutions).

Regret Audits Can Be a Powerful Intentional Living Tool

After reading Pink’s book, I decided to create my own regret audit process that can be done once a year, or more frequently if you choose.

1. Using the four core regrets as a guide, list your specific regrets from the time period you are auditing and decide what core regret “bucket” they fall into, if applicable. Some examples could include not getting outside in nature enough, forgetting someone’s birthday, or not starting a new business.

2. For each regret, ask yourself whether there is any silver lining, or “at least” counterfactual thinking that you can find. Perhaps it was important to save money for the new business which is why you delayed it for a few months. “At leasts” may not be applicable for every regret, but it’s worth asking.

3. For each regret, ask yourself whether it is a regret of action or inaction and if it represents an open or closed door. Forgetting someone’s birthday is a regret of inaction but it represents an open door if the person is still alive. If any regrets are “closed” in nature, practice self-compassion and forgiveness to work on letting that regret go.

4. For action regrets with an open door, ask yourself if the situation can be repaired and if so, how. For inaction regrets with an open door, ask yourself what the cost is if you continue not to act. How will you feel if you spend the next year not taking steps to start a business? What is the cost to your health if you continue to spend most of your time behind a computer screen instead of getting fresh air?

5. What objections or limiting beliefs are holding you back? Write down all the stories you are telling yourself as to why you can’t take action, and then ask yourself if these are actually true. Byron’s Katie’s Four Questions may be a helpful resource for this.

6. What can you do now to mitigate or eliminate this regret? Do you need to speak up? Make a call? Plan a trip? Step outside? Make a list, and then make your action plan.

On the Other Side of Regret, There is Hope

A regret audit can help you work through past regrets and choose differently to minimize future regrets, but a regret-free life isn’t the goal. Rather than avoiding regret, we can recognize that regret makes us human and can instruct us on how to live a more intentional life aligned with our values. But once we know the actions that can help mitigate or eliminate our regrets, it is up to us to push past the inertia, awkwardness, or fear and press into the hope that there is something better on the other side. At the end of his book, Pink offers this mantra to help us embrace and appreciate the power of regret: “Regret makes me human. Regret makes me better. Regret gives me hope.”

A regret audit is an informative exercise for living a more intentional life. Writing your eulogy is another powerful exercise. My free guide will take you step-by-step through the process.