Regret is an emotion we all encounter at some point in life, whether it’s about a missed opportunity, a risky decision that didn’t pay off, or a path not taken. It’s the feeling that can haunt us long after the decision has been made, often fueled by the thought of what could have been. But what causes regret to sting so deeply? Why do we sometimes feel more regret when we take action, while other times, it’s the inaction we lament? The fear of regret plays a significant role in our decisions—sometimes leading us to act impulsively, other times paralyzing us with indecision. By examining real-life examples and psychological research, we can better understand how the fear of regret shapes our choices and how we can manage it to avoid making irrational decisions.
Two Stories of Regret
When we experience regret, it typically stems from the belief that we made the wrong choice in a particular situation. But regret can often be more complicated than simply wishing we had made a different decision. It can involve comparing the outcome of our choices to hypothetical alternatives—what could have been. Let’s explore this concept through the experiences of Paul and George.
Paul owns shares in Company A, a company he’s followed for a while. Over the year, Paul became aware of a promising new opportunity: Company B, which appears to be growing rapidly. He wonders if he should sell his shares in Company A and buy into Company B. He weighs the pros and cons but ultimately decides to hold onto his shares in Company A. At the end of the year, Paul discovers that if he had bought shares in Company B, he would have made $1,200 more. Despite his solid reasoning for sticking with Company A, Paul feels deep regret. The feeling of missed opportunity nags at him, and he can’t help but think, “What if?”
In contrast, George, who owns shares in Company B, decides to sell his position and purchase shares in Company A, convinced that the latter is poised for growth. However, by the end of the year, George learns that, had he kept his original investment, he would have made $1,200 more. George feels a stronger regret than Paul, even though their financial outcomes are identical. Why? The core difference between the two men lies in their actions. While Paul remained passive, George actively made a change.
The psychological weight of George’s decision is greater because he took a risk, stepping out of the status quo, only to realize that his decision was ultimately poor. On the other hand, Paul can rationalize his choice by reminding himself that he didn’t make any changes, which provides a buffer against regret. Paul can tell himself that, at least, he didn’t take a risk and fail. This scenario illustrates a fascinating truth: the person who actively chooses to change or take a risk tends to experience greater regret because the emotional burden of making the wrong choice feels heavier when action is involved. Meanwhile, the person who sticks to the familiar path often experiences regret more lightly because their decision feels less “personal.”
Action vs. Inaction
The story of Paul and George is not just about missed opportunities—it also speaks to the broader concept of action versus inaction. We often assume that those who act will bear the brunt of regret, as their decisions are the ones that involve risk. However, in some cases, inaction can carry a more significant emotional burden than action.
Consider the example of the venerable publishing house that stubbornly refuses to adopt the new trend of e-books. The company has long been a cornerstone in the publishing industry, focusing on traditional paper-based books. The owner, firm in his beliefs, dismisses the idea of digital books as a fad. He is content with his tried-and-true methods despite the increasing popularity of e-books. Meanwhile, other publishers take the plunge into the digital world, creating ebook strategies in hopes of securing their place in the future of publishing. Over time, however, this new direction proves disastrous for many of them. Nine publishers that embraced e-books go bankrupt. But then, the last holdout—the traditional publishing house—also fails.
While the nine publishers who actively moved into the digital space failed due to their decisions, the last publisher arguably garners the most sympathy. Why? This company’s failure might feel less like a failure of choice and more like a victim of external forces. The publisher stuck with paper books for so long is now the victim of a larger, inevitable shift in the market. The public is more likely to sympathize with the publisher that didn’t act—because inaction feels safer, more rational, and less likely to result in catastrophe. This situation illustrates how inaction can, paradoxically, cause more regret and sympathy than taking bold steps that fail.
The example underscores a deeper psychological dynamic: when people face uncertainty, they often feel safer doing nothing. The fear of regret associated with an active decision feels far worse than the regret of missing an opportunity because, in the latter case, one can always rationalize that they didn’t make a risky choice. The publisher’s refusal to adapt may seem like a safe, wise decision initially, but it ultimately leads to a loss. This demonstrates how human psychology tends to favor inaction—sometimes, the act of doing nothing invites the heaviest consequences.
The Exception That Provokes Sympathy
Kahneman’s concept of the exception as the figure who attracts sympathy helps us understand the human tendency to focus on the unusual or atypical case. In Thinking, Fast and Slow, Kahneman provides an example that highlights this phenomenon: following a plane crash, there’s always a person who claims to have changed their flight at the last minute—perhaps they decided to leave a day earlier or later. By making a minor change to their plans, this person avoids the fatal crash.
This person becomes an exception. They weren’t supposed to be on that flight, but a twist of fate led them to change their plans. However, the other passengers on the flight were booked from the beginning and had no choice but to board the ill-fated plane. Despite their identical fate, we tend to feel more sympathy for the individual who changed their flight because they represent an exception to the norm. The person who changed their flight is perceived as unlucky, while the others are seen as following the inevitable.
The key here is that regret feels more intense when the decision is exceptional, as it draws attention to the fragility of our control over life’s outcomes. The person who alters their flight plans is seen as a victim of chance—had they made the same choice as everyone else, they would have been just another passenger. Because their action was a deviation, it becomes more poignant. Their regret is amplified by the notion that they could avoid tragedy, but fate intervened. This psychological tendency explains why people who stray from the expected course often garner more empathy.
This is a prime example of how exceptions—or the perception of them—play a large role in how we perceive and feel regret. It’s not just the outcome but the story behind it. The unusual story elicits more sympathy, and the regret that comes with it feels more tangible.
Regret and Irrational Behavior
One of the more dangerous consequences of the fear of regret is how it influences decision-making in ways that are not always logical. People often act conservatively, driven by the desire to avoid the deep discomfort of regretting their choices. This tendency is especially noticeable in high-stakes environments like the financial markets. Traders, for example, are known to engage in “performance panic” at the end of the year—rushing to sell off risky investments before their year-end evaluations, even if they believe in the long-term viability of those investments.
This irrational behavior is driven by the fear of being judged for making a poor decision, which could lead to missed bonuses or even a tarnished reputation. In this context, the fear of regret overrides rational analysis. Despite their deep understanding of the market and their confidence in their investments, traders often fall prey to conforming to the masses, dumping their more exotic assets in favor of safer, more conventional stocks. This is a clear example of how the fear of future regret causes individuals to make decisions based more on emotional comfort than sound reasoning.
The same psychological forces are in everyday situations, such as the difficulty we face when discarding old items. Many people hold onto things they no longer need—a pair of shoes that have long been out of use or an old gadget gathering dust. The thought of getting rid of these items triggers a fear: what if, one day, they need them? Even though the likelihood is low, the fear of regret holds us back. The emotional attachment to objects is driven by the potential regret we might feel later on, preventing us from making a logical decision to let go.
In both examples, the fear of regret leads people to act in ways that don’t necessarily align with their best interests. Whether a hasty financial decision or a reluctance to part with unused possessions, the fear of making the wrong choice can cloud judgment, preventing individuals from making more rational, beneficial decisions.
The ‘Last Chance’ Illusion
One of the most powerful triggers of regret is the notion of a “last chance” opportunity. The idea that something is available only once creates an artificial urgency that can lead people to act impulsively. Marketing campaigns thrive on this concept, often using phrases like “only a few left” or “limited-time offer” to convince consumers to act quickly. But the fear of regret—rooted in the idea that this might be the only opportunity—can make people make irrational choices.
Consider the case of the safari brochure promising the “last chance to see a rhino before the species becomes extinct.” While it’s true that rhinos are endangered, this brochure manipulates the idea of scarcity, convincing potential customers that they must act now or risk missing out on this rare experience. If you’ve never cared about seeing a rhino before, why would you suddenly drop everything to go on a safari just because it’s framed as a “last chance”? Yet, the fear of regret makes it feel like this is a once-in-a-lifetime opportunity, even if the event has no real urgency.
The same psychology applies to more significant investments. Imagine you’ve always dreamed of owning a house and heard that only a few lakefront plots remain on the market. The advertising emphasizes that “there is only one plot left!” The fear of missing out and the belief that this is a rare opportunity pushes you to act quickly, buying the plot at a premium price. Yet, in reality, lakefront properties will likely continue to come on the market, and this perceived “last chance” is simply a marketing tactic designed to create a sense of urgency.
These examples highlight how the fear of regret can lead to impulsive behavior. The sense of missing out on something perceived as rare can cloud our judgment, making us feel like we need to act now, even when there’s no real need to do so. This fear of regret and the illusion of scarcity can lead us to make decisions that are not in our best long-term interest.
Conclusion
The fear of regret is a powerful force that influences nearly every decision we make, from our financial choices to the items we hold onto, just in case. Whether it’s the fear of not acting or of having taken the wrong action, regret often leads us down paths that don’t serve our best interests. We may act conservatively, follow the crowd, or impulsively seize what we perceive as a “last chance” opportunity. Understanding how this emotion drives us allows us to make better, more rational decisions. By acknowledging the role of regret in our decision-making, we can navigate life’s choices with greater clarity, avoiding the trap of fear and acting with greater confidence and purpose.
This article is part of The Art of Thinking Clearly Series based on Rolf Dobelli’s book.