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The Hidden Math of Disappointment
A deeper look at why unmet expectations hurt and what to do with the pain
Issue 44/ July 2025
Read time: 9 minutes
The Shift
This sucks.
There is a strange kind of silence that follows disappointment. It’s not the calm of acceptance or the stillness of peace. It’s the quiet that exists in the gap between what we imagined and what came to be. It’s the quiet unraveling of a future we were starting to believe in. A pause that hums with grief, confusion, and tension.
We often talk about failure. We talk about resilience. But we don’t talk much, at least not seriously, about disappointment.
Many people recoil from disappointment. After all, it’s one of those emotions that feels physically unpleasant, tight in the chest, heavy in the stomach, contracting rather than expansive.
It doesn’t dissuade the feeling, but if you are disappointed, it means you were engaged in the most human of acts. Envisioning possibility.
For all of us, disappointment can become a fork in the road. When our expectations collapse, we instinctively reach for new assumptions about ourselves, about others, about what’s safe to hope for. For some, it is a single data point to pivot off of. For others, it can redraw the entire map of what to expect in life.
Disappointment Is Not Regret
In their pioneering work on decision theory and emotional cognition, Marcel Zeelenberg and colleagues clarified a vital distinction:
Regret arises when the outcome was bad because of our own choice.
Disappointment happens when the negative outcome was outside our control.
If you conflate the two, you’ll instinctively try to fix disappointment by doing what works for regret: becoming more cautious, more perfectionist, more self-critical. But those tools don’t work here.
Disappointment isn’t a symptom of doing something wrong or even right. It’s the emotional cost of participating in uncertain, complex systems where not everything is yours to control.
The Formula: Expectations, Probability, Magnitude
Zeelenberg found that disappointment isn’t just a feeling. It’s a formula, modulated by three core variables:
Expectation – the altitude at which you were flying. The higher your imagined outcome, the greater the distance to fall. We’re not just reacting to reality. We’re reacting to the version of it we were already living in our heads.
Probability – the perceived likelihood that the desired outcome would occur. A high-probability event that fails shocks us more than one we thought unlikely.
Magnitude – the value or importance of the outcome. Disappointment over missing coffee with a friend is not the same as disappointment over a collapsing marriage. The emotional weight of the outcome determines the emotional weight of the disappointment.
These elements interact. A missed opportunity that was both highly probable and highly valued is far more damaging than one that was neither.
The Responses to Disappointment
Our default reaction to disappointment is often to wriggle free from it. It’s uncomfortable, and most of us will do whatever it takes to escape that sensation.
We might blame others: “They’re a bunch of idiots who couldn’t see how much I would have brought to their team.”
We may even have an urge to rally support for our perspective. Partly for comfort, but also to regain a sense of power. When disappointment makes us feel small or unseen, agreement from others can feel like proof that we still matter.
Blame can feel empowering in the short term. But over time, it erodes our agency. It subtly shifts the responsibility for our lives onto someone else’s choices.
Alternatively, we might turn the blame inward: “If I had prepared better,” or “If I had been more regimented, I wouldn’t be sick.”
This line of thinking can give us a comforting illusion of control. If we’re at fault, at least we can fix it, right?
But self-blame often overshoots. It ignores what was out of our hands and brings with it shame, embarrassment, and guilt.
Still other times, we avoid the experience altogether. We go silent, distract ourselves, or tell ourselves we didn’t really want it anyway. We downgrade the dream so the disappointment doesn’t sting as much.
But for some of us, when disappointment hurts badly enough, it doesn’t just bruise the moment; it rewires how we move through the world. We reduce risk. We shrink expectations. We begin to opt out of meaningful opportunities so life doesn’t have a chance to negatively surprise us. We call it “being realistic,” but often it’s a quiet resignation dressed in rational language.
Control, Agency, and the Honest Audit
Before we rush to fix or reframe disappointment, I have to acknowledge a simple truth: it sucks. It’s deeply human, and deeply unpleasant. And sometimes, no amount of cognitive reframing or philosophical perspective will stop it from hurting.
Yet, there has been a lot of research on how to mitigate disappointment, how to regulate expectations, lower risk, or reinterpret outcomes. And that work is useful. But it doesn’t replace the emotional part.
So here is what the research says: Bearing disappointment becomes easier when we track our expectations precisely and are explicit and honest about what we’re hoping for.
It’s natural to project into the future when we pursue something connected to our values or dreams. And that’s not something to eliminate. Daydreaming is not dangerous in itself. It’s essential. Progress depends on the ability to imagine better realities.
But there’s a boundary between imagining and expecting. When we live too long in the mental simulation of what we hoped for, we lose sight of what was actually in our control, what outcomes are possible, and maybe even probable. And most detrimentally, we tie our sense of identity to the fantasy.
This is where the honest audit begins:
Were my expectations realistic? Sometimes, the hardest truth is that we never had a real shot. We just really wanted one. And that hurts.
What was within my control, and what wasn’t?
Did I take responsibility for my part, without absorbing blame that belonged elsewhere? As a rule: own 100% of your side of the equation, but not 1% of external variables.
How long and deep did I daydream? Did I make life plans based on a fantasy or on reality?
Being With Disappointment
Yes, there are ways to soften the blow. But I don’t want to give the impression that disappointment is a feeling to be optimized away. It’s part of being a conscious, invested human being. If you care about anything deeply, you will eventually grieve its loss or transformation.
Sometimes, the most important thing we can do is allow disappointment to be what it is. To sit with it. Be vulnerable to it. To name what was lost. Feel the weight of something we hoped for that didn’t arrive. To invite meaningful conversation and a deeper connection with those around us. Not to dramatize it, not to bury it, but to metabolize it.
When we do that, when we actually let it move through the system, rather than calcify beneath it, disappointment becomes something else entirely. It becomes fuel. It becomes clarity. It becomes the raw material out of which new direction, and even renewed motivation, can emerge.
Meaning, then, is not what we seek after disappointment. It’s what we build with it.
The Essentials
Your Weekly Toolkit
THE GENTLE STARTUP
Gentle startups are a communication strategy designed to bring up concerns or complaints without criticism, blame, or hostility. Instead of launching into a conversation with accusation (“You never listen to me”), the gentle startup focuses on feelings, and describes specific situations, making it easier for the other person to hear and respond non-defensively. This is research from Dr. John Gottman, a renowned psychologist and relationship researcher from the Gottman Institute.
CREATING A GRIEF RITUAL
Grief rituals are intentional acts that help us process loss, honor what was, and create space for emotional integration. Across cultures, rituals have long provided a structured, communal way to express sorrow and remember what has been lost. Whether it’s lighting a candle, writing a letter, or holding a symbolic goodbye, these practices offer a sense of continuity and healing when language alone isn’t enough.
CYCLE OF AVOIDANCE
The Cycle of Avoidance is a self-reinforcing loop where discomfort is dodged rather than addressed, leading to short-term relief but long-term consequences. Each time we avoid a difficult emotion, task, or conversation, we reinforce the belief that it's too overwhelming to face—making it even harder to engage with in the future. Over time, this cycle erodes confidence, increases anxiety, and keeps us stuck in patterns that prevent growth or resolution.
Means a lot to me that you show up every week!
Hope you stay a little curious and find a little more joy this week.
💌 If you enjoyed this issue, please share it with someone who might also benefit. Help me build a community of thoughtful, intentional people who are committed to small shifts and meaningful growth. Together, we can spread a little more light and care into the world.
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