Context #1
Christine: I heard that Jane's going to break up with her boyfriend.
Veronica: Yeah, she caught him cheating on her. I would break up with him too if I were in her shoes.
Context #2
David: Due to the recent budget cuts, I have to lay off 2 people next month.
Steve: That's going to be hard because I know your employees all have families to care for. I wouldn't want to be in your shoes.
David: Gee, thanks!
Meaning: "to be in someone's shoes" means to be in their situation. It is used to think about what your would do if you were facing the same things that they are facing.
