Most of what we call empathy is a guess made from our own position. We hear what happened to someone, and we run it through what we would feel if it had happened to us. The result feels like understanding. It is not. It is our life, with their name on it.
This matters because the substitution is invisible. Nobody experiences their empathy as a projection. It arrives as a feeling of closeness, and the feeling is real. What is missing is the other person.
The self that stands there

When you imagine someone's situation, you do it from where you stand. Your reactions, your history, your sense of what is reasonable all stay in place. They are the instrument doing the measuring. So the reading you get is not a reading of them. It is a reading of how your particular self would respond to their circumstances.
For small things, this approximation is good enough. Most daily life runs on it. But for the situations where understanding actually matters — grief, humiliation, a decision that looks irrational from outside — the approximation fails precisely because the other person is not you. Their history produced reactions yours would never produce. The more different their life, the worse your guess.
What real understanding costs

Real understanding goes further, and it costs more. It requires letting go of your own reactions, your own past, your own frame of what is sensible, and living through the situation as them. Not picturing it. Occupying it.
This is not a mood. It is a structural shift. You are temporarily removing the self that would otherwise stand between you and the thing you are looking at. For a while, there is no outside position from which to judge, compare, or protect.
The protection you do not notice

Here is the part people skip. Other people go through immense hardship. If you keep yourself intact while looking at that, you are protected. You are also outside.
The intact self is not neutral. It is doing a job. It keeps your own continuity unbroken while you approach something that might break it. That is a reasonable thing for a mind to do. But it means the safety and the distance are the same thing. You cannot keep one and drop the other.
This is why understanding is often avoided without anyone deciding to avoid it. The mind chooses approximation not because it is lazy but because approximation is safe. The cost of understanding is that, for a while, you are not defended.
The choice inside every attempt

So there is a choice hidden in every attempt to understand someone. Stay yourself and stay approximate. Or let yourself go for a while, and know what it actually was.
Neither is wrong in every case. Some situations do not warrant the cost. But it is worth knowing which one you are doing, because the two feel similar from the inside and produce very different results. One gives you a comfortable picture of a person. The other gives you the person, at the price of briefly not being you.
If this pattern of connection failing while feeling like connection is familiar, the essay on levels of awareness goes further into where the gap opens.