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How to Leverage Regret for a Better Future

Round Editorial

New York Times bestselling author Daniel Pink talks about how to use regret as a tool to lead a more meaningful and productive life.

Regret comes in many forms and at all stages of life – but whatever the specific situation, it’s one emotion that makes us uniquely human. And despite its prevalence, this negative feeling is complicated, and even, at times, embarrassing and taboo. Yet there are ways to get past regret, and even harness it to build character.

As part of our RoundAbout event series, New York Times bestselling author Daniel Pink spoke about the many dimensions of regret and what his global research reveals about this very complex emotion. Here are five takeaways from the conversation:

1. There are four distinctive types of regrets

Pink’s World Regret Survey research of more than 16,000 people around the globe showed that there are four categories of regret people commonly experience.

  • Foundation regrets: if I’d only done the work. These regrets encompass failures to be responsible, such as career or financial situations. People who experience foundation regrets often experience them as they evaluate the choices they made earlier in life.
  • Boldness regrets: if I’d only taken the chance. Boldness regrets are far reaching, and encompass both personal regrets, like not traveling or taking a romantic leap; or professional regrets, such as staying in a bad job too long or not standing tall in leadership. Often, when people play it safe they regret not taking the chance.
  • Moral regrets: if I’d only done the right thing. These regrets hurt other people, such as marital infidelity, bullying, and other breaches of moral duty. Only about 10 percent of regrets fall in this category, in part because Pink says most people are generally morally driven.
  • Connection regrets: if I’d only maintained that relationship. Although this may sound like it’s grounded in romantic regrets, this includes the full swath of relationships people have, from partners to colleagues to family. Connection regret represents the biggest category.

2. Decisions can be made to either “maximize” or “satisfy” decisions

To temper potential regret, people often anticipate how they may feel and subsequently make decisions based on the potential for negative feelings from a wrong choice. For example, someone who chooses a less interesting job at a large corporation, instead of a more exciting role at a startup, due to fears of job security in a fledgling company. There are two ways people can approach decisions to help mitigate regret down the line.

The first is “maximizing” a decision. In this approach, you make the decision based on where you might experience the most regret. These decisions are seen as urgent and significant. This approach is important, but also emotionally exhausting – and “people who constantly maximize are miserable,” Pink says.

In “satisfying” decisions, you make a “good enough” decision for the time being, and understand the potential regret is actually comparably insignificant. If you don’t choose the “right” thing for dinner, for instance, there are no far-reaching ramifications.

3. Decide when to “maximize” and when to “satisfy”

Subsequently, one of the healthiest things you can do, Pink says, is try to sort out when to maximize decisions versus just satisfying them (in other words, chill out). It’s impossible – and even “debilitating” – to give every choice immense weight. This is called “optimization.”

People who live with the least regret, are able to identify when to maximize and generally let the rest go.

4. Leaders should disclose regrets to normalize them

Regret is absolutely normal. Often, society signals that you shouldn’t have negative feelings – that something is “wrong with you” if you feel regret, or even that you’re weak for not constantly expressing positivity. The key to busting this taboo, according to Pink, is airing these regrets.

Often, we fear that people will think less of us if we reveal or missteps or expose vulnerabilities, but more than three decades of research shows that not only will people not judge you, they often think more of you. This may require pushing through awkwardness, but is ultimately hugely beneficial for leaders and teams.

Leaders who share their regrets create more trustworthy and productive cultures.

5. Learning from regret requires embracing the discomfort around it

Many of us want to learn from our regrets, but it’s not as simple as looking back on choices and saying that you’ll take the other option next time you encounter a similar situation. There’s a great deal of discomfort in reckoning with regret.

All over the world, people are “allergic” to experiencing the discomfort of realizing you weren’t perfect in the past. There’s an immense amount of pressure to not make mistakes, and even hide from them. But in order to have a redemption story, you have to recognize that you weren’t perfect, so that you can learn from the past to do better in the future.

Ultimately, understanding the types of regrets you have as well as how to internalize them can build you into a better person. Sharing your regrets to normalize the feeling can help you become a stronger leader, and set you up to make the best decisions in the future.

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