The Unreliable Nature of Regret: Why It Doesn’t Always Lead Us to the Right Decision
For years, I believed that regret could be a powerful motivator. When facing indecision, I would often ask myself: “How will I feel if I don’t take this step?” The thought of future regret seemed to provide clarity, pushing me to take action, move forward, and make choices that aligned with my goals. It was a mental shortcut I used to nudge myself toward decisions. And, for a time, it worked.
But as I’ve reflected more on the role of regret in decision-making, I’ve come to a realization: regret isn’t the reliable guide I once thought it was. In fact, regret is an unreliable emotion—difficult to predict and even harder to fully understand in hindsight.
The Faulty Logic of Regret
At first glance, the idea that regret is unreliable may seem counterintuitive. After all, isn’t regret simply the feeling we experience when we realize a decision we made was wrong, or that we missed out on something? Doesn’t it help us learn from our mistakes and avoid repeating them?
While there’s truth to this, regret is far from a clear-cut indicator of what was “right” or “wrong.” In fact, it’s often more a reflection of the information we have at a particular moment than a true measure of the decision’s quality.
Consider this idea: regret is heavily influenced by the information we gain after a decision is made. When we don’t have access to an alternative path, it’s easy to feel regret about the one we’ve chosen, imagining how things might have turned out differently. But here’s the catch—this kind of regret is driven by a form of selection bias. In other words, we can’t regret what we don’t know.
Asymmetric Opportunities and Selection Bias
A concept I came across recently in an article about asymmetric opportunities really shaped my thinking on this topic. The author described how regret is often a result of selective information. Here’s an example:
Imagine you’re in a relationship that’s clearly not working, and you finally decide to end it. You don’t have access to an alternate reality where you stay in the relationship, so you never get to see how it might have played out. On the other hand, if you stay in the relationship too long and later realize it’s a waste of time, your regret comes from knowing that you missed an opportunity to leave earlier.
The key point here is that regret is not necessarily about the decision you made—it’s about the information you gained after the fact. When you can’t see what might have happened if you’d chosen differently, it’s easy to convince yourself that the road you took was the wrong one. But you don’t really know for sure.
This bias also applies in other areas of life. For example, consider a round of company layoffs that don’t affect you. If you leave the company during this time, you may feel relieved, thinking you’ve escaped a sinking ship. But what if the layoffs actually pave the way for your rapid promotion? Without that counterfactual information, you’ll never truly know if staying was the right choice.
This example demonstrates the fundamental flaw in basing decisions on the avoidance of regret. Regret often has little to do with what was actually the better decision. Instead, it’s influenced by the information we happen to learn after the fact—and this information is always incomplete.
The Illusion of Certainty in Hindsight
When we look back on our choices, we tend to believe that hindsight gives us a clearer view of the past. But how often do we truly know we made the right decision? The truth is, we almost never have access to all the possible outcomes that might have resulted from a different choice.
Take my decision to start writing online and pursue a life of travel. I’ve often thought about the alternative paths I could have taken. What if I had chosen to stay in a stable job at a bank instead of following my passion for writing? What if I’d stayed at home rather than embarking on a journey to see the world? The truth is, I can’t imagine an alternate universe where I made those choices, because they’re not the ones I’m living. The life I’ve chosen feels like the only reality.
And yet, there’s always the nagging question: Could I have made a better choice? Could there have been an even richer path, one I’m not privy to because I didn’t choose it? The possibility of a better outcome—a counterfactual life that never came to be—remains forever unknown, leaving me to wonder if I made the right decision.
This feeling of “what might have been” is something many of us experience. Sylvia Plath captured this existential struggle beautifully in her metaphor of the fig tree. In her story, the protagonist stands before a tree with many branches, each one representing a potential future. Overwhelmed by the choices, she is paralyzed by the fear of making the wrong one. The tree becomes a symbol of opportunity, but also of uncertainty.
Can We Trust Regret?
Ultimately, we must confront the fact that regret is a deeply unreliable guide. While it may be a useful tool for motivating us in certain moments, it doesn’t offer us a true measure of the quality of our decisions. We often regret what we don’t know, not what we experienced.
Regret is shaped by selective information. When we only have access to one reality—the one we’re living—we base our interpretations of past decisions on what we’ve learned from that single path. The road not taken is always the one we imagine could have been better, but we can never truly know.
So, instead of allowing the fear of future regret to guide our decisions, perhaps we should learn to embrace uncertainty. Every decision we make comes with its own set of unknowns, and that’s okay. The future is always going to be a mix of possibilities, and our understanding of the past is just as malleable as the future itself.
Next time you’re faced with a tough decision, instead of fearing what you might regret, try to make peace with the fact that, in the grand scheme of things, no choice is truly certain. And that’s okay. What matters is making the best decision you can, with the information you have, and letting go of the need to be certain about everything. Because in the end, regret will always be a reflection of what you can’t know—no matter how hard you try.
