Failure, Regret, and Curiosity.
A Story in Three Acts.
Menachem Dahan, Psychotherapist – Bay Harbor Islands
In my clinical experience, regret stands out as one of the most influential emotions a person can feel. It surfaces most powerfully around choices, decisions, and the paths a person takes, precisely because those are the moments where responsibility for an outcome cannot be placed anywhere else. People do a great deal to avoid feeling it. Decisions get delayed, opportunities get passed over, and entire patterns of living get built around the goal of never having to feel it.
Regret in Context.
At the core, people are looking for genuine peace, which means two things. First, that the peace itself is genuine, not a performance of calm or a temporary lull between storms. Second, it comes as a result of being genuine, of living from a place that is actually true to who a person is rather than a place built on avoidance or image management. This kind of peace does not mean the absence of pain or difficult feelings. It is not a life free of hardship or discomfort. It refers instead to a minimal amount of tension or friction between a person and the life they are actually living, a sense that the life being lived and the person living it are not working against each other.
There are different avenues that lead a person to recognize this need. Some realize they are constantly chasing surface-level experiences like pleasure and validation. These are real parts of life, and there is nothing wrong with wanting them. But when they become the only goal, when they become the measure of a good day or a good life, frustration inevitably follows. Life is more substantial than that. It has depth and weight that pleasure and validation alone cannot provide. The difficulty is that this substance rarely feels as potent in the moment as those lighter, more immediate experiences do. A person can know intellectually that connection or meaning matters more than a compliment or a rush of pleasure and still feel the compliment land harder in the moment.
Another avenue comes from a different recognition, the sense that something is getting in the way of simply being genuine, of simply living. This might show up as a vague dissatisfaction even when things are going well, or a feeling of performing a life rather than living one. People who arrive at this avenue often cannot immediately name what stands in the way. They only know that something does.
When a person tries to grasp the core of who they are, going directly sounds intuitive. What do I actually think and feel about myself, beneath the roles and habits? But asking the question so plainly often proves difficult and ineffective. Simply sitting down and asking directly rarely produces an honest answer, because the question is too big and too exposed to face head on. The self is such a subtle and refined personal experience that a person has to take another route to access it. Direct introspection tends to produce the answer a person already expects, or the answer they think they should give, rather than something new.
Regret becomes one of those routes, one of those angles that reveals what a person feels and thinks about himself, and it does so in a specific way. It opens the door to a feeling of failure, which is already uncomfortable enough on its own, but what sits underneath that failure is often what actually frightens a person. Failure forces a person to leave the well built self they have grown comfortable with, the version built out of competence, control, and a working sense of who they are, and underneath that familiar structure is something less defined, less proven, and far less comfortable to sit with. This is the deeper reason a wrong choice can feel disproportionate to the situation itself. The practical consequences of a bad decision can usually be managed. What is harder to manage is the exposure that follows, the sense of being asked to stand somewhere unfamiliar without the usual supports.
That exposure places a person in a space that centers on who they are beneath the protections, stories, and accomplishments they typically point to in order to grasp who they are. Those things, a career, a reputation, and a role in the family, usually do a good job of standing in for identity, and regret has a way of stripping them away, at least temporarily. What surfaces beneath all of it is an unsettling sense of doubt about whether the self is a house of cards, about how solid the belief a person holds in himself really is once the usual supports are pulled back. There is real fear in finding out, and that fear is often strong enough that a person would rather not look.
This fear connects to something larger. Choice sits at the core of being human, and because of that, it is a source of great anxiety. To possess real agency, to actually control the direction of one’s own life, sounds like something to be grateful for, and is often spoken about that way in passing, but taken seriously, it is daunting. It means that outcomes belong to the person who chose them, and that ownership feels like the opposite of safety and security. It is far more comfortable to imagine that life happens to a person than to fully accept that a life is, in large part, being authored by that same person.
This is why making a decision, even a minor one, opens that door a bit for many people. A decision that goes wrong and the regret felt afterward raises a question underneath the surface, one about whether failure opens a door to a room a person does not want to enter, a room that reminds them they control their life and that most failures and shortfalls trace back to their own hand. Whether that can be handled and, if not, how a person walks through life with any confidence after learning that about himself becomes the real weight carried forward from the experience. It is rarely the failed choice itself that lingers. It is what the failure seemed to reveal.
That weight lands hardest because confidence and calm have always come from feeling secure, and this regretful experience reveals something else underneath that sense of security. It reveals fear, a tendency to spiral once failure arrives, and a concern that this reaction reaches beyond the single moment and colors daily living. A creeping anxiousness can settle in once a person knows what waits on the other side of failure, on the other side of regret, and life afterward can start to feel like something to be managed carefully so as not to trigger that room again.
The Role of Being Curious.
This is where curiosity enters. Curiosity does not remove the pain or the discomfort. It does not make the feeling of failure disappear or soften the exposure underneath it. What curiosity does is take the automatic narrative that many people fall into, the narrative that treats a single failure as a full verdict on character, and interrupts it.
Instead of immediately concluding something damning about the self, curiosity turns toward the raw spot and simply asks what is happening here. It does not rush to fix the feeling or explain it away. It stays with it long enough to ask what is actually behind it. What is this fear made of. What does the spiral after a failure seem to be protecting? What is a person actually scared of when a decision goes wrong, and what is it that a person wants underneath that fear, the security being reached for, the version of himself being protected? These questions do not need to be answered in a single sitting. Curiosity is comfortable letting them sit unresolved, returning to them the way a person returns to something worth understanding rather than something that needs to be solved on the spot.
This is what separates curiosity from judgment. Judgment moves quickly to a verdict, deciding in an instant what a failure says about a person’s worth or character. Curiosity moves slowly and stays close to the actual experience, treating the fear, the spiral, and the discomfort as information rather than as proof of anything final. It allows a person to say that this is a part of me, not the whole me, and to keep exploring from that steadier place instead of retreating from it.
This changes the relationship a person has with regret itself and with choice going forward. Regret no longer has to function as the automatic warning system that keeps a person from acting, the voice that makes each decision feel like a test with only one acceptable outcome. A person can still feel regretful when a choice goes wrong. The feeling is not being avoided or minimized. What changes is what that feeling is allowed to mean. It becomes something to sit with and understand rather than something that forces a person back into the cycle of protecting the well-built self at all costs. This is what makes it possible to keep choosing, to keep taking action in a life that matters, without needing every outcome guaranteed in advance. The cycle described above, where a bad choice threatens to expose something unbearable underneath, loses its grip once a person has practiced staying curious about that exposure instead of fleeing from it. Choice becomes livable again, not because the stakes have gotten smaller, but because the person has found a way to survive being wrong.
Curiosity means saying, beyond simply learning about the feeling, that there is no fear here, only a wish to learn more. Tell me more about myself, curiosity says, rather than tell me the verdict. And in that shift, from verdict to inquiry, a person begins to find the very peace that was being sought from the start, not a life without pain, but one with minimal friction between the person and the life they are living, genuine because it was arrived at honestly, and lasting because it did not depend on never failing again.
Menachem Dahan is a psychotherapist in South Florida. mdahanpsychotherapy.com
