Why Do We Regret the Past? The 2 Conditions of Regret

This article is an excerpt from the Shortform book guide to "The Power of Regret" by Daniel Pink. Shortform has the world's best summaries and analyses of books you should be reading.

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Why do we regret the past? What are the conditions that lead us to feel regret?

Having regrets is natural for humans. We regret past relationships, missed opportunities, and embarrassing moments. According to Daniel Pink, the author of The Power of Regret, for regret to arise, two conditions must be present: personal agency and opportunity.

Continue reading to learn what leads us to regret things.

Regret Condition #1: Personal Agency

Why do we regret our past sometimes? Pink clarifies that people only feel regret if they believe themselves to be the cause of their negative situation. The comparison between their two possible presents will only produce regret if their negative situation is due to their past actions or decisions. 

While almost everyone experiences painful emotions when events don’t work out the way they’d hoped, if they don’t consider themselves the cause of their negative situation, they feel disappointment rather than regret

(Shortform note: Pink distinguishes disappointment from regret and focuses his advice on overcoming regret. However, disappointment can be just as painful and debilitating, and it is worth mentioning how psychologists recommend approaching this emotion. Many people make their disappointments feel worse because they catastrophize—”I didn’t get this job and so I’ll never have a satisfying career,” or they personalize—”This romantic partner rejected me because I don’t deserve a happy relationship.” Instead, psychologists recommend that you learn from your disappointments: Set realistic expectations, but keep trying.)

That said, Pink offers one important caveat: Sometimes people incorrectly attribute an outcome to their actions when it was actually beyond their control. For example, someone who is laid off from their job may attribute the situation to poor work performance, when actually their company simply decided to eliminate the role entirely. This false attribution may lead them to regret inconsequential mistakes, such as coming to work late once or making a typo on an email. As we will see later in this guide, correctly analyzing the situation is an important part of growing from regret.

(Shortform note: The tendency to blame yourself for everything that goes wrong in your life may be a symptom of anxiety. Psychologists argue that people with high anxiety will falsely attribute outcomes to themselves because it soothes the feeling that they lack control—even though blaming themselves may be painful, it could be less scary than being at the mercy of fate.)

Regret Condition #2: Opportunity

Pink explains that people only regret past decisions if they believe they could have chosen otherwise. If there wasn’t a choice they could have made to change the outcome, they can’t really attribute their present situation to this choice. Therefore, people who have more opportunities in a given situation tend to have more regrets.

For example, you’re more likely to regret your career choice if you live in a town with a diverse range of industries because you had lots of potential career options. However, if you live in a small town with only one or two industries, you have fewer alternative paths to take and therefore fewer opportunities to imagine how your life could have been different. You’re less likely to regret your career choice because you’ve given up fewer alternative paths. 

(Shortform note: In The Paradox of Choice, Barry Schwartz expands on why more options leads to a higher probability of regret. He explains that the more options you have, the higher the opportunity cost of the choice. An opportunity cost is simply the economic term for what is lost by pursuing one course of action over another. Since you must let go of more options, the opportunity cost of your decision goes up with the number of alternative choices you could have made—and therefore making a choice creates a stronger sense of loss.)

Why Do We Regret the Past? The 2 Conditions of Regret

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Like what you just read? Read the rest of the world's best book summary and analysis of Daniel Pink's "The Power of Regret" at Shortform.

Here's what you'll find in our full The Power of Regret summary:

  • A look at why most people feel regret, and what causes it
  • The three worst ways to deal with regrets
  • The five-step process for turning regrets into advantages

Katie Doll

Somehow, Katie was able to pull off her childhood dream of creating a career around books after graduating with a degree in English and a concentration in Creative Writing. Her preferred genre of books has changed drastically over the years, from fantasy/dystopian young-adult to moving novels and non-fiction books on the human experience. Katie especially enjoys reading and writing about all things television, good and bad.

One thought on “Why Do We Regret the Past? The 2 Conditions of Regret

  • February 2, 2024 at 12:35 am

    I’m impressed with this. This is what I was missing in my life


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