You can’t really walk in someone’s shoes. You can ask what the walk has been like.

Imagining your way into another life has limits, and pretending otherwise is how people end up confidently wrong about somebody else’s situation. You have your own history in the way; the best you can manage from inside your head is a version of them made out of you. Asking is different. It brings back information you could not have invented.

Next time you are sure you know how someone feels, ask instead of assuming. Use an open question and let the answer be surprising rather than fitting it to what you expected. Listening without preparing a reply is most of the skill, and it takes practice.