Regret is a powerfully strong emotion that most people have felt, despite all of the self-help advice stating that regret is foolish and that it should be avoided. When asked, “How often do you look back on your life and wish you had done things differently?”— only one percent of respondents said never; in fact, 82 percent of respondents said it’s a question they think about at least occasionally (with about half of those saying frequently or all the time).

Both regret and disappointment arise when an outcome is not what you wanted, counted on, or thought would happen; but, with disappointment, you often believe the outcome was outside of your control. Not so with regret – you believe the outcome was caused by your own decisions or actions – it’s your fault.

In an effort to learn more about the nuances of regret, Daniel Pink and his team surveyed nearly 4,500 Americans to collect their attitudes about it. At the same time, they also launched a website to collect regrets from around the world. To date, Pink and his team have collected more than 16,000 regrets from people in 105 countries. The American Regret Project, in connection with the World Regret Survey, form the largest pool of data ever collected about what humans regret. One of his most interesting findings is that there is a deep structure to regret – four categories into which regrets can be placed (with a key lesson, Pink says, each category is meant to teach):

Category 1 – Foundation Regrets: These regrets represent failures to be responsible, conscientious, or prudent, and they leave you thinking, “If only I had done the work.” A lot of finance- and health-related regrets are in this category.

The lesson: Think ahead. Do the work. Start now.

Category 2 – Boldness Regrets: Over time, humans are much more likely to regret inaction – the chances they didn’t take. Those opportunities to start a business, chase a true love or something less grand, like learning a new language or how to play an instrument. They leave you thinking, “If only I had taken that chance.” Inaction regrets outnumbered action regrets in Pink’s survey by two to one.

The lesson: Ask him/her out. Take the trip. Start the business. Speak up on behalf of yourself or someone else.

Category 3 – Moral Regrets: This category represents those times when you had a choice and took the low road. These regrets made up the smallest of the four categories, representing only about 10 percent of the total regrets Pink and his team collected. They found that while they are the smallest in number, they are the greatest in variety and often, the most individually painful. They leave you wondering, “If only I had done the right thing.”

The lesson: When in doubt, take the high road.

Category 4 – Connection Regrets: These regrets happen when you neglect the people who matter to you and who help establish your sense of wholeness. These regrets made up the largest category – humans have a massive amount of regret about fractured or unrealized relationships. These regrets sound like, “If only I had reached out.” These regrets can either be “open door” – you can still do something about it; or “closed door” – the circumstances are impossible to change. What often thwarts repair attempts is your own flawed thinking – you massively overestimate how awkward or bothered the receiver will feel while also underestimating how positively they are likely to react.  A US Army soldier shared with our team that his mother’s death had created a rift in the family such that he hadn’t spoken to his sister in years. On our course day off, he took the train from Philadelphia to New York City and showed up at his sister’s apartment unannounced. She was home, opened the door, and burst into (happy) tears.

The lesson: If it’s a closed door regret, do better next time. If it’s an open door regret, do something now.

In an effort to discover more about people’s regrets, I asked a small group the following: Do you believe A: I have regrets, and they have taught me a lot; or B. No regrets. My mistakes brought me to this point in my life. Sixty-eight responses were collected in 24 hours and the results were as follows: 42 people answered B (62%) and 26 people answered A (38%). This one simple ask resulted in powerful conversations about shame, missed opportunities, the evolution of one’s personal regret philosophy, and regret generally.

The “no regrets” ethos is a strong one, but as Pink points out, it’s also dangerous. In adults, the true absence of regret can be a sign of serious illness including a range of psychiatric and neurological diseases. Regret is actually a marker of a healthy and maturing mind. People who strongly identify with the “no regrets” philosophy may have simply learned how to optimize regret. At its essence, life’s misses are powerful teachers, pointing you closer to what you really need and value: that you want a measure of stability, to grow and explore the world and your place in it, that you want to do the right thing, and long to love and connect with others.  What do you wish you had done differently?


Please click here to order my book, Beating Burnout at Work: Why Teams Hold the Secret to Well-Being and Resilience.