The Becoming of Possibility: 01/15/26

Thursday, 15 January 2026

Empathy Without Collapse: 3 What We Actually Mean When We Say “I Understand You”

“I understand you” is a strong claim.

Stronger, in fact, than we usually acknowledge.

We say it easily, often with good intentions. Sometimes we say it to reassure, sometimes to calm, sometimes to signal solidarity. But when someone responds, “No, you don’t,” the force of that rejection is unmistakable.

It is not a disagreement about tone.

It is not a complaint about warmth.

It is a rejection of the claim itself.

So what, exactly, are we claiming when we say we understand another person?

Understanding is not agreement

A useful place to begin is with what understanding clearly is not.

To understand someone is not necessarily to agree with them. We regularly understand positions we reject, reasons we do not accept, and actions we would not take ourselves. In fact, disagreement often presupposes understanding: it is hard to argue coherently against something you do not yet grasp.

This already tells us something important.

If understanding does not require agreement, then it cannot depend on emotional alignment alone. Agreement often involves shared evaluation, shared concern, or shared affect. Understanding does not.

Understanding is compatible with distance.

Understanding is not approval

Nor does understanding require endorsement.

We can understand why someone did something while still judging it wrong. We can understand a motivation without excusing it. We can understand a fear without sharing it.

This matters, because it shows that understanding operates at a different level from moral response. It does not settle what should be done; it makes intelligible what was done or is being claimed.

Again, this suggests that understanding has more to do with orientation than with feeling.

What understanding actually enables

When someone says, “You understand me,” what they are usually acknowledging is not that you feel the same way they do, but that you can navigate their perspective.

You know:

what they take to be at stake
what counts as a reason for them
what would surprise them
what would offend them
what would feel like a misrepresentation

You may not share any of this. But you can track it.

Understanding, in this sense, is practical. It shows up in what you can anticipate, not in what you feel.

If you understand someone, you can predict where they will push back, what clarifications they will demand, and which objections will miss the point. You know when a response will land as relevant and when it will feel beside the issue.

This kind of understanding is visible in action.

“That’s not what I meant”

Few phrases reveal the limits of understanding as clearly as this one.

When someone says, “That’s not what I meant,” they are not asking for sympathy. They are asking for a correction in orientation. They are pointing out that their meaning has been placed in the wrong position—interpreted against the wrong background, framed by the wrong assumptions, or directed toward the wrong stakes.

Notice how often emotional attentiveness fails here.

You can be patient, caring, and emotionally present, and still hear what someone says in a way that systematically misplaces its significance. The issue is not that you didn’t care enough. It’s that you didn’t locate the meaning correctly.

Understanding falters not because feeling is absent, but because orientation is off.

Meaning is relational

At this point, we can say something that sounds obvious but carries weight.

Meaning is not just content. It is content-in-relation.

What someone says means what it means against a background of concerns, expectations, distinctions, and stakes. Change that background, and the same words can mean something else entirely.

To understand someone, then, is not simply to register what they say or how they feel. It is to situate what they say within the space of relevance that gives it its force.

This is why paraphrase can feel insulting rather than helpful. A paraphrase that preserves content but misplaces relevance does not feel like understanding at all.

Understanding as orientation, not access

We are now close to a crucial shift.

Understanding does not require access to another’s inner life. It does not require sharing their feelings. It does not even require imagining “what it would be like” to be them.

What it requires is the ability to orient oneself within the structure of their perspective.

This is a discipline, not a sensation.

It involves recognising where meaning is being made, what distinctions matter there, and how claims hang together from that position—even when that position is not one you occupy.

Once again, this explains why empathy can survive disagreement. You can orient yourself to a perspective you reject. You can understand a position you oppose. You can track a logic you find unconvincing.

Feeling with is optional. Orientation is not.

Where this leaves empathy

If empathy is to involve understanding—and not just accompaniment—then it must involve this kind of orientational work.

That does not make empathy cold or detached. On the contrary, it makes it demanding. It requires restraint: the willingness not to overwrite another’s meaning with your own reactions, however well intentioned.

In the next post, we will take a decisive step.

We will ask where meaning is made in the first place—and why understanding another person requires recognising not just what they say or feel, but where their experience is being organised from.

This is where empathy begins to show its real structure.

Empathy Without Collapse: 2 Feeling With Is Not Understanding

When people talk about empathy, they almost always talk about feeling.

Feeling with.

Feeling for.

Feeling what another feels.

This makes intuitive sense. Our earliest lessons about empathy are often framed this way: imagine how they must feel; put yourself in their shoes; try to feel it from their side. When empathy works at all, it often feels like a kind of emotional closeness or resonance.

So if empathy so often goes wrong, a natural response is to assume that we haven’t felt enough, or haven’t felt accurately enough.

But there is a problem with this assumption—one that shows up as soon as we look closely at how emotional “feeling with” actually behaves in practice.

When feeling with works—and when it doesn’t

There are situations where emotional alignment does genuine good.

When someone is grieving, frightened, or overwhelmed, the sense that another person is emotionally present can be deeply stabilising. Feeling accompanied matters. Resonance matters. Silence shared in the right emotional register can be more helpful than any explanation.

But notice something important: these are situations where understanding is not the main demand.

What is needed is presence, not interpretation. Regulation, not orientation. Care, not clarity.

Now contrast this with situations where understanding is at stake:

a disagreement about motives
a conflict over responsibility
a misunderstanding about what mattered or why
a moral or political disagreement
a moment where someone says, “You’re not hearing me”

In these situations, emotional alignment often fails—or even makes things worse.

You can feel deeply with someone and still misunderstand them.

You can share their emotional intensity and still miss their point entirely.

At times, emotional alignment increases the sense that you understand, while leaving the other person feeling even more misread.

Emotional resonance is not directional

One reason for this is that emotion, on its own, is not very precise.

Emotions tell us that something matters, but not how it matters, to whom, or in what terms. Two people can feel intense anger together while disagreeing completely about its source, its justification, and its implications. They can share grief without sharing meaning. They can resonate emotionally while diverging interpretively.

Emotional resonance amplifies salience, but it does not specify orientation.

This is why feeling with someone can be genuinely moving and genuinely uninformative at the same time.

The problem of projection

There is a more serious risk lurking here.

When empathy is framed primarily as feeling what another feels, it becomes very easy to substitute my emotional responses for your perspective. I imagine how I would feel in your situation, and then treat that imagined feeling as insight into your experience.

This is not done maliciously. It is often done with the best intentions.

But the result is a quiet shift:

Your experience becomes intelligible only insofar as it matches my own emotional repertoire.

At that point, empathy stops being a way of reaching toward another and becomes a way of confirming oneself.

This is why people so often respond to empathic gestures with:

“That’s not what it’s like at all.”

Sympathy, identification, and contagion

Part of the confusion around empathy comes from the fact that it is rarely distinguished from several neighbouring phenomena.

Emotional contagion: catching another’s mood or affect
Sympathy: feeling concern or care for someone
Identification: seeing oneself in another’s situation

All of these can feel empathic. All of them can accompany empathy. None of them guarantees understanding.

You can sympathise with someone while misunderstanding their reasons.

You can identify with someone while erasing what makes their experience distinct.

You can catch someone’s emotional tone while misreading its meaning entirely.

The trouble begins when these experiences are treated as sufficient.

Why disagreement is so revealing

Disagreement is where the limits of feeling-based empathy become most visible.

In disagreement, emotional alignment is often impossible—or actively misleading. Feeling with the other person may require feeling something you reject, or rejecting something you feel strongly yourself. The emotional landscape becomes contested rather than shared.

And yet, disagreement is precisely where empathy is most needed.

If empathy were primarily a matter of shared feeling, then empathy would collapse the moment people diverged emotionally. But our moral intuitions tell us something else: that it is still possible—and still important—to understand someone you disagree with.

This tells us something crucial:

Empathy must be able to survive emotional divergence.

Which means it cannot be defined in emotional terms alone.

A first separation

At this point, we can begin to make a careful distinction—without denying the reality or importance of feeling.

Emotional resonance can support empathy.

It can motivate it.

It can accompany it.

But it cannot constitute it.

Feeling with someone is neither necessary nor sufficient for understanding them. Sometimes it helps; sometimes it hinders; sometimes it gives us false confidence precisely when we most need caution.

If empathy is to be something we can rely on—especially in situations of tension, conflict, or difference—it must involve something more disciplined than emotional alignment.

What this opens up

Once we stop treating feeling as the core of empathy, a different set of questions comes into view:

What does it actually mean to understand another?
What must be in place for one perspective to be intelligible to another?
How can understanding preserve difference rather than collapse it?

These are not emotional questions. They are questions about orientation, perspective, and meaning.

In the next post, we’ll begin to approach empathy from this angle—not by abandoning what people experience when they empathise, but by asking what must be going on for those experiences to count as understanding at all.

Empathy does not fail because we fail to feel.

It fails because feeling, on its own, is not enough.

Empathy Without Collapse: 1 Why Empathy So Often Goes Wrong

Empathy is one of those things we rarely question until it fails.

Most of us grow up assuming we know what empathy is. We’re told it matters. We’re encouraged to practise it. In moments of conflict, misunderstanding, or pain, the advice arrives quickly and confidently: try to empathise.

And often, we do.

We listen carefully.

We imagine how the other person might feel.

We try to “put ourselves in their shoes.”

And yet—despite all this goodwill—something still goes wrong.

The other person pulls back.

They say we’re not really listening.

They tell us we’ve missed the point entirely.

Sometimes they’re polite about it. Sometimes not.

But the message is familiar: whatever you’re doing, it isn’t working.

This is not a rare failure. It is common enough to feel almost built in.

The quiet puzzle of failed empathy

What makes this puzzling is that empathy is usually treated as a moral or emotional virtue. When it fails, we tend to explain that failure in personal terms:

I wasn’t empathetic enough.
They were too defensive.
The situation was too emotional.
I didn’t choose the right words.

Occasionally this is true. But it doesn’t explain the pattern.

Empathy fails not only when people are careless or cruel, but often when they are sincere, attentive, and trying their best. It fails between people who care deeply about one another. It fails in families, friendships, workplaces, and political conversations alike. It even fails—perhaps most painfully—when both parties believe they are being empathetic at the same time.

At that point, the problem can no longer be dismissed as a lack of goodwill.

Something structural is going wrong.

“I understand how you feel”

Few phrases are more closely associated with empathy than this one.

And few are more likely to provoke irritation.

“I understand how you feel” is often meant kindly. It can even be offered tentatively, with care. Yet it regularly lands badly. Instead of reassuring, it can sound presumptuous. Instead of opening space, it can close it.

Why?

It’s tempting to say that the problem is tone, or timing, or emotional sensitivity. But notice something subtler: the phrase fails even when spoken gently, even when followed by attentive listening, even when the speaker genuinely believes it to be true.

The issue is not rudeness.

The issue is not arrogance.

The issue is not lack of concern.

The issue is that empathy is being attempted in a way that does not reliably connect.

When empathy increases misunderstanding

One of the most unsettling features of empathy is that it can increase confidence while decreasing understanding.

People often become most certain that they understand another precisely at the moment when they least do. They feel aligned. They feel emotionally attuned. They feel they’ve “got it.”

And yet the other person feels unseen, misread, or overwritten.

This creates a peculiar asymmetry:

One person feels closer.
The other feels erased.

When this happens repeatedly, empathy starts to feel dangerous rather than healing. It becomes something to resist rather than welcome. “Don’t tell me how I feel” becomes a defensive necessity, not a rejection of care.

If empathy were simply a matter of emotional attunement, this pattern would be hard to explain. Emotional attunement should reduce misunderstanding, not amplify it.

Unless—of course—we are misunderstanding empathy itself.

The temptation of easy explanations

There is no shortage of explanations for empathic failure.

Some focus on psychology: different attachment styles, personality traits, emotional literacy.

Others focus on morality: selfishness, defensiveness, lack of compassion.

Still others focus on culture: power, identity, lived experience.

Each of these explanations captures something real. None of them fully accounts for the persistence of the problem.

Because even when we control for all of these factors—even when people are emotionally literate, morally serious, and culturally aware—empathy still breaks.

And it tends to break in the same ways.

That regularity should give us pause.

When something fails predictably across contexts, the problem is rarely just personal. It is usually conceptual.

A suspicion worth taking seriously

Here is the suspicion that will guide this series:

Our everyday understanding of empathy is too crude to support the work we ask it to do.

That does not mean empathy is unimportant.

It does not mean we should abandon it.

It does not mean people who value empathy are naïve.

It means that empathy has been overloaded with expectations it cannot meet, and defined in terms that obscure its actual structure.

As a result, we keep trying to use it—and keep being surprised when it collapses under pressure.

Why this matters now

Empathy is not just a private virtue. It is increasingly treated as a social solution.

We are told empathy can bridge political divides, heal social fragmentation, repair institutions, and restore trust. Workshops are designed to teach it. Metrics are invented to measure it. Leaders are praised or criticised according to whether they appear empathetic enough.

And yet, at the same time, many people report feeling more misunderstood than ever.

This is not because empathy has suddenly become less important. It is because we are relying on a conception of empathy that does not scale—and does not even function reliably at close range.

Before empathy can do the work we want it to do, we need to understand what kind of thing it actually is.

Where we’re going

This first post has not offered a definition of empathy. That is deliberate.

Instead, it has tried to make a modest case:

that the familiar idea of empathy—however well intentioned—is not robust enough to explain either its promise or its failures.

In the posts that follow, we will proceed carefully.

We will not begin by dismissing feelings or denying their importance.

We will not reduce empathy to technique or training.

We will not pretend the problem is simply that people are doing empathy “wrong.”

Instead, we will start by disentangling empathy from things it is commonly confused with. Only then will we be in a position to ask what empathy actually involves—and why it is both fragile and demanding.

If empathy so often goes wrong, it is not because we care too little.

It is because we have not yet been precise enough about what caring, in this case, really requires.