The Certainty Trap: On the Obsessional Search for Control and the Freedom of Not Knowing

Imagine someone middle-aged who’s increasingly become concerned about their limited time on earth and their eventual mortality. These are not particularly unusual fears. Now envision some of their other worries, such as the fear of dying in an airplane crash, a motor vehicle collision, or some other terrible accident. In fact, suppose this person has a variety of worries, from the fear of a loose brick falling from a building and killing them instantly to the possibility that some inconspicuous illness is running out their clock. Imagine this person worries about their parents aging and eventually passing away. Suppose they fear the many ways their parents’ death might arrive, and the profound sadness it would bring them.

If you can picture someone like this, you can easily conceive that they are never short on worry. You might hope their constant worrying was at least productive, but imagine things not quite working this way. Imagine instead their mind endlessly generating unknowable threats. Caught in a trap of their own making, they react to abstract future possibilities as immediate threats requiring prompt resolution. The more this person thought, the more possibilities they found, and the more anxious and uncertain they became. Even when they did seem to advance to another concern, they would often find themselves back at a previous worry, wondering if they had somehow missed something.

Envision a scenario in which this individual, exhausted from all their rumination and, seeking relief, contacts their psychiatrist to request medication to help settle the mind. “I need a pause from all this thinking,” they might wish. Conceive that they manage to secure a prescription, and only minutes later, phone their therapist to ask whether they should take the relief-offering pill. How could they know if they actually needed the medicine, they might ask. Surely, they might say, medication could become habit-forming or perhaps they might be missing out on an opportunity to self-regulate without it. It would be hard for someone like this to know for sure.

Even a decision they initially sought out with absolute conviction could demand exhaustive re-evaluation, and a fresh round of reassurance from anyone willing to listen.

This is what an obsessional way of approaching life can look like, not to be confused with obsessive-compulsive disorder, which is a clinical diagnosis based on specific symptoms and diagnostic criteria. Here, “obsessional” describes a pattern in which a person attempts to manage uncertainty primarily through repeated thinking, mental review, and reassurance-seeking. They may feel compelled to think things through exhaustively, avoid making the wrong decision, and reach a level of certainty that allows them to move forward without doubt.

Why Thinking Harder Doesn’t Help

There is a problem with the strategy of such mental compulsions: we are surrounded by uncertainty at all times. There is no amount of thinking that can rid one of all doubt. But those with an obsessional way of approaching life often struggle to accept this.

In her book Psychoanalytic Diagnosis, American psychologist Nancy McWilliams describes the obsessional-oriented individual. In her chapter on obsessive-compulsive personality organization, she tells the story of a woman who, after becoming pregnant and wanting to keep all of her options open, chose two obstetricians at two different medical centers because they had different philosophies about childbirth. The woman spent the duration of her pregnancy trying to determine which doctor and which hospital would be the better choice. Still undecided even while in labor, she waited so long trying to decide which hospital was appropriate that she ended up giving birth at the nearest clinic, by whomever was attending at the time.

This cautionary story illustrates what can happen when such a person postpones a decision until the “perfect” choice becomes clear. McWilliams writes, “In the effort to keep all their options open,” those with this kind of personality organization can end up feeling like they have no options at all. They can waver for only so long before life steps in to decide for them.

One Decision After Another

The obsessionally oriented person overlooks another important reality: even if they could somehow identify the perfect decision, that choice would not eliminate the need for further decisions related to that very option. Said differently, choosing a door doesn’t end the journey but simply unlocks a whole new set of choices. It is those subsequent, day-to-day decisions—not the initial pick—that ultimately determine whether a choice feels “right.”

Imagine trying to decide between four universities. Perhaps one of them eventually appears to be the obvious choice. The curriculum is most aligned to what they want to pursue professionally. They value family, and it’s closer to home. Student life appears more interesting. The campus feels more vibrant, and the surrounding areas appeal to them. Finally, there is a decision that seems easy to make.

But then what?

They still have to attend classes. They must still dedicate themselves to their studies. They have to address challenges that arise, decide when to ask for help, and when to figure things out on their own. They will have to navigate difficult social situations and decide which peer groups are worth pursuing. They will make mistakes. And ultimately, as their academic journey continues, they will have to decide whether the decision to attend their chosen university feels right. They will likely need to make adjustments along the way.

These considerations can be difficult for an obsessionally oriented person to fully appreciate. They spend so much time and energy trying to decide that they miss a fundamental fact: life is one decision after another. There is no decision that gets us out of having to make more decisions.

Psychologist, university professor, and founding fellow of the Academy of Cognitive and Behavioral Therapies Chad LeJeune makes a similar point in his book, “Pure O” OCD. He discusses the famous short story “The Lady, or the Tiger?”, written by Frank R. Stockton and published in 1882. In it, a barbaric king forces a man to choose between two doors. Behind one door is a woman who will become his bride. Behind the other is a tiger that will kill him. It’s easy to understand why someone facing such an undesired predicament would want to hold off making a choice as long as possible.

LeJeune points out that the excessive worrier's situation is not really like this. Their problem is that they imagine a future as though only one door contains a clearly good outcome and all others contain a clearly bad one. In reality, we almost never fully know the kind of future that awaits us behind either door. As LeJeune puts it, “The perception that there is a happy and an unhappy outcome behind the doors ... is actually an illusion.”

What Preparedness Actually Looks Like

Recognizing that there is no hallway in which we can remain indefinitely while we contemplate certitude raises another question. If the illusion of total control keeps us frozen in the doorway, then what does preparedness actually look like?

In a lecture, Alan Watts, the British self-described “philosophical entertainer” who introduced Buddhist, Taoist, and Hindu ideas to Western audiences in the mid-20th century, describes the traditional training of fencing. He tells the story of live-in apprentices who, living with their “master,” must go about their ordinary daily activities knowing that, without warning, their teacher will attack them with a practice sword consisting of loosely tied bamboo rods. Learning quickly to avoid the pain from such an attack, the students initially prepare themselves by attempting to anticipate where and when the next attack will come from. They become increasingly tense and on edge as they try to anticipate correctly.

But the attack can come from anywhere, and eventually, the student learns that there is no way to prepare for an attack from every possible direction. Sooner or later they grasp that trying to do so actually interferes with their ability to respond. Watts explains: “If you prepare for an attack from a specific direction and it comes from some other direction, you have to withdraw the direction in which you had expected it and send your energy in another direction. And that takes time. So what you do is, you go around with a mind of no expectation.”

Watts’s observation captures one main predicament faced by the never-ending ruminative thinker. The problem is not simply that they give themselves the unattainable task of accounting for every possible outcome with sureness. It’s also that they continuously direct their energies toward something, somewhere out there in the future, while failing to experience their present moments with a sense of enjoyment.

The person who spends all day preparing for the next catastrophe is not necessarily becoming better prepared for it. Instead, they may be becoming increasingly tense, increasingly focused on an imaginary future, and less able to respond naturally when life does take an unexpected turn.

Learning to Live With Not Knowing

Helping someone with this way of approaching life can be difficult. Family and friends living alongside someone like this may find that their patience is put to the test. Nancy McWilliams notes that even therapists who work with these kinds of individuals sometimes secretly wish they could tell them to “shit or get off the pot.” It can be easy to overlook that the mental toll these individuals endure causes them considerable anguish.

When someone is suffering this way, it may be tempting to reassure them that things will be alright. It can be appealing to help them review the facts, consider the possibilities, and predict outcomes. But support in the form of more deliberation, more certainty-seeking, can easily draw those trying to help into the very process that keeps the sufferer stuck. The work, then, becomes helping them tolerate the discomfort of not knowing, even when that means they feel less sure of their decisions.

The hope for people like this is that they can learn to live with the unknown and still feel okay. They do not have to enjoy uncertainty. But if they can make peace with life’s inherent unknowability, they can develop confidence in their ability to face whatever life eventually brings.

At some point, the person has to become willing to step through the door without knowing exactly what is waiting on the other side. And most often that is where some of the freedom they have been looking for begins. Not in finally knowing what will happen, but in discovering that they do not have to know.

Sources

LeJeune, C. (2023). “Pure O” OCD: Letting go of obsessive thoughts with acceptance and commitment therapy. New Harbinger Publications.

McWilliams, N. (2011). Psychoanalytic diagnosis: Understanding personality structure in the clinical process (2nd ed.). Guilford Press.

Watts, A. (2020). Leave it be: Alan Watts on the art of meditation [Audio recording]. Sounds True.

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