Dwight: Aiko, help me out here. I want to dive into the concept of "undoing certainty"—why it matters and how we can build a strong habit of practicing it in a way that truly benefits us.

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Aiko: That’s a fascinating idea, Dwight. Undoing certainty seems like a way to stay flexible, open-minded, and responsive to complexity.

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Dwight: To understand why undoing certainty matters, we should first explore the harm that excessive or misplaced certainty can cause in our lives and in the lives of those we care about. If we took a moment to reflect, we might realize that many of our certainties aren’t actually justified.

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Aiko: That makes a lot of sense. When we're overly certain, we risk making poor decisions, shutting down new perspectives, or even damaging relationships.

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Dwight: Let’s try categorizing three key areas where we tend to believe things that aren’t actually true. The first is what we might call the optimism bias—where hidden optimistic assumptions lead us to underestimate time, effort, or cost when making plans, whether as individuals, teams, organizations, or even governments. 

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Aiko: That’s a strong starting point. Optimism bias can make us overcommit, underprepare, or fail to anticipate obstacles. Do you think this happens more because of wishful thinking or because we genuinely don’t see the complexities ahead?

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Dwight: At its core, this happens because we’re addicted to the comfort of feeling safe, in control, and able to predict outcomes more accurately than we actually can. It also lets us enjoy the immediate gratification of counting our chickens before they hatch. This addiction is fueled by our habit of automatically accepting the certainty of our assumptions—especially when they align with our desires and give us that quick emotional payoff.

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Aiko: That’s a sharp insight. So, it’s not just optimism but a deeper craving for psychological security. The tricky part is that this habit runs so automatically that we rarely notice it. How do you think we can start interrupting this cycle?

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Dwight: We’ll get to how to interrupt this later. For now, we’re just focusing on why we do it and the harm it causes.

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Aiko: Got it. So, this need for certainty and control makes us blind to our overly optimistic assumptions, which can lead to disappointment, frustration, wasted resources, and even distrust when things don’t go as planned. 

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Dwight: I suggest that whenever we feel disappointed, blame others or ourselves, get frustrated, or see something as a "failure," it’s often because we set ourselves up with an expectation rooted in a self-inflicted and inappropriate level of certainty.

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Aiko: That’s a powerful way to frame it. It implies that much of our emotional turmoil isn’t caused by reality itself but by the rigid expectations we impose on it. 

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Dwight: First, if we build the habit of recognizing when we’re placing too much certainty on an outcome, and we still choose to move forward—fully aware of and accepting the risks—then even if things don’t go as we’d like, we’ve already accounted for that possibility and won’t be shaken by it. We've accepted risk that we're happy to take as part of playing the game of going for different things we'd like to have.

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Aiko: That makes a lot of sense. It shifts us from being reactive to being intentional, reducing unnecessary stress. So, in a way, undoing certainty doesn’t mean avoiding action—it means acting with a clearer, more flexible mindset. 

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Dwight: Every action we take carries some level of risk. For instance, deciding to brush our teeth has an almost negligible risk—we don’t even consider the possibility of being unable to do it. However, if we’re planning to start a new business with the goal of quitting our current job within six months, the level of risk is significantly higher. Even with consistent effort, unforeseen circumstances could disrupt our progress, making the likelihood of achieving that goal in six months most probably even greater than 50%.

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Despite this, we can still choose to move forward. By acknowledging and accepting risk as an inherent part of the process, we not only increase our chances of success but also develop the resilience to embrace whatever outcome unfolds. Engaging fully in life’s challenges means recognizing that uncertainty is part of the journey—and that’s what makes the pursuit worthwhile and exciting.

 

When we shift our perspective to stop seeing risk as something that shouldn’t be there, we accept it as a natural part of pursuing what we want. While we can work to reduce risk, that always has limits—often lowering risk in one area increases it elsewhere. In the big picture, this approach makes us more likely to achieve our goals, helps us stay unfazed when things don’t go our way, and builds a stronger reputation for reliability—both with ourselves and others.

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Aiko: That’s a powerful mindset shift. Instead of resisting uncertainty, we integrate it into our decision-making, which makes us more adaptable and trustworthy.

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Dwight: The second key area where we tend to have too much certainty is what I call the pessimism bias. While some people lean more toward optimism bias and others toward pessimism bias, all of us likely shift between the two depending on the area of life we’re dealing with.

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Aiko: That’s an interesting balance—sometimes we overestimate how well things will go, and other times we’re too certain they’ll go badly.

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Dwight: The pessimism bias shows up in thoughts or statements like, "There's no point in asking—they’re just going to say no," or "I’ve already been turned down for three positions, so getting the type of job I want is impossible." or "I've looked for my wallet for thirty minutes. It's gone forever."

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Aiko: That kind of thinking locks us into self-fulfilling prophecies, where we stop trying and reinforce our own fears.

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Dwight: The costs of pessimism bias become clear when we step back and see the bigger picture, but in the moment, this self-deception has strong immediate benefits. First, it gives us a solid excuse to avoid taking action, helping us sidestep the fear of pursuing something uncertain—or even letting us appear as if we’re trying while secretly holding back. Second, and closely related, it shields us from the risk of disappointment if things don’t go our way.

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Aiko: That makes a lot of sense—it’s a protective mechanism, even if it ultimately limits us. It’s like trading long-term potential for short-term comfort. 

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Dwight: The third key area where we fall into unfounded certainty is in our use of certain words or fuzzy distinctions that seem clear and solid but really aren’t. Common examples hide in words like should, should not, good, bad, right, wrong, deserving, undeserving, loyal, obligation, maybe—and many related terms that I call toxic or fuzzy.

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Aiko: That’s an interesting angle—these words create a false sense of clarity when in reality, they’re often loaded with assumptions and personal biases.

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Dwight: Let’s take the word "should," which people often assume has a clear meaning—whether they’re using it themselves or hearing it from someone else. Many times, statements using should feel like factual claims that could be proven or disproven. Sometimes, they actually can be—like if I tell someone, “If you're going to use the garden hose, then you should turn the water on first.” That’s testable within a given context.

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But in contrast, imagine a mother telling her daughter, who is considering leaving her husband, “You shouldn’t do that. That would be cruel.” What’s really being asserted here? Is the mother saying that because she and others (perhaps the husband as well) would view leaving him as cruel, her daughter risks their disapproval? If we’re going to use should in a way that is factually grounded, that’s likely the only meaning that holds up to scrutiny. Yet, it’s rare for people to recognize this actual factual basis when using should—or when hearing it from others. We think that the word "should" means something more than warning about someone's possible disapproval including that of the speaker, when, in fact, it rarely does.

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Aiko: That’s a great breakdown. The problem is that should often disguises personal values, social pressures, or emotional reactions as objective truths. It’s easy to accept or resist these statements without questioning what’s really being communicated.

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Dwight: I’d venture to say that many words we use as if they’re clear and objective distinctions are actually pseudo-distinctions. They seem to distinguish something real, but if they were true distinctions, they wouldn’t carry the hidden weight of judgment. These words often contain a built-in layer of judgmentalness rather than being neutral assessments. Prime examples include good, bad, right, wrong, fair, unfair, deserve, don’t deserve, loyal, disloyal, loser, greedy, selfish, lazy, jerk, and bitch.

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Aiko: That’s a sharp observation. These words often feel like factual labels, but they’re really just reflecting the speaker’s perspective, values, or emotional state.

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Dwight: All such pseudo-distinctions play a major role in driving our motivations and clouding our judgment, making us more certain about things—or people—than the actual evidence supports.

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Aiko: That’s a powerful point. These words don’t just distort our thinking; they also reinforce emotional reactions that make us double down on our assumptions. 

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Dwight: Some might argue that a lack of certainty can also be a problem—and that’s true. I often remind people that they actually know more about how to do something or how things work than they claim. But I’d suggest that this, too, is just another form of misplaced certainty—certainty about not knowing something, when in fact, they do know or could know something to a reasonable degree. I often hear people justify their uninformed actions by repeating the cliché, “The only thing certain is change.”

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Aiko: That’s an interesting reversal—being too certain about uncertainty itself. It’s almost like a way of surrendering responsibility, as if uncertainty means they can’t take meaningful action.

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Dwight: They are cashing in on the short-term benefits of a specific kind of pessimistic certainty.

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Aiko: That makes sense—it lets them avoid effort, responsibility, or the risk of being wrong while feeling justified in doing so. 

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Dwight: Byron Katie, in her teachings and workshops, relies on a simple yet powerful process called The Work (Four Questions and a Turnaround) to help people transform their lives. This process starts with identifying a distressing situation and the core belief that defines the suffering—such as "My mother doesn’t love me." Two of the key questions in the process are: "Is that belief true?" and, if the answer is "yes," then "Are you absolutely sure that it’s true?" Other steps involve uncovering evidence that challenges the certainty of those beliefs.

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Aiko: That’s a great example of undoing certainty in a way that can be deeply liberating.

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Dwight: We should always be cautious of over-generalizing, but I’d argue that, with few exceptions, all human suffering (not just pain, but suffering) and preventable dysfunction—whether in how we deal with ourselves, others, or reality—stems from our addiction to seeking more safety and certainty than the available evidence actually justifies. Notice that I used the word "should" in the former sentence. Its use here is clear and valid since what I assert is obvious and open to be proven or disproven.

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Aiko: That’s a bold but compelling assertion. It suggests that suffering isn’t just about external events but about how tightly we cling to illusions of control and certainty. 

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Dwight: Now, let’s shift our focus to practical methodologies and new habits we can develop to help us undo this toxic certainty.

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Aiko: Sounds good. Since this kind of certainty is so automatic and deeply ingrained, where do you think is the best place to start—awareness, daily practices, or something else?

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Dwight: The first essential step in dismantling the habits, beliefs, and structures that sustain dysfunctional certainty is to gain increasing clarity on just how much it actually—or likely—dominates our lives.

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Aiko: That makes sense. Without recognizing its grip, there’s no real motivation to change it. 

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Dwight: One of the key habits that keeps dysfunctional certainty in place is our tendency to automatically believe the fully formed thoughts and beliefs that flow through our minds—and often out of our mouths—without ever examining or questioning them. Statements like "I knew she was going to disappoint me," "I know she would never betray me," or "It’s a dog-eat-dog world" go unchallenged, reinforcing our certainty without real scrutiny.

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Aiko: That’s a powerful insight. These thoughts feel like observations, but they’re really just unverified assumptions masquerading as truth.

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Dwight: Most of us have never developed an internal gatekeeper—a kind of fact-checker—to vet the thoughts and beliefs that arise in our minds. As a result, these unchecked beliefs end up driving at least 99% of our life choices, both big and small. We haven’t built the habit or the desire to actively look for evidence or reasoning that could nullify or modify these beliefs. Nor have we cultivated the eagerness to discover anything that might bring our beliefs more in line with reality.

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Aiko: That’s a striking way to put it. Without that gatekeeper, we’re essentially running on autopilot, mistaking assumptions for truth. 

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Dwight: Confirmation bias is powerful in all of us, making it harder for our beliefs to align with reality. It pushes us to seek out and accept only the evidence that reinforces what we already think. Developing a joy and delight in discovering that something we believed—even strongly—was either not true or only partially true is a habit worth cultivating and cherishing.

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Aiko: That’s a refreshing perspective—turning what most people see as a threat into something exciting. 

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Dwight: I realize this discussion has grown too expansive to pack into a single essay. I’m sure we’ll revisit this topic in the future, exploring more powerful ways to undo certainty—by which I mean, undoing the certainty we hold despite having available evidence that does not justify the level of certainty we maintain.

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Aiko: That’s a great distinction to end on. Undoing certainty isn’t about rejecting confidence altogether—it’s about aligning our certainty with what the evidence actually supports. Looking forward to continuing this conversation down the road!