If an ex asks "do you ever wish things had turned out differently?" In a conversation, what would you think she is referring to?

She had previously been talking about jobs we had each had so I answered in the context of how things would be different if I had gone for a different career. But I'm not sure whether that's the context she was asking about.
If an ex asks "do you ever wish things had turned out differently?" In a conversation, what would you think she is referring to?
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