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In that case, should you try to fake your own situation as to not get pity or should you be honest? When I encounter people who are financially ahead than me I just think that it will be me someday... That I will reach that level too where I would be able to buy whatever they can. So basically I try to make them my inspiration. Do you take inspiration from the rich people or do they make you feel worse?
It depends on the character of the successful person. If we meet someone who is financially more successful than us and acts arrogant or haughty, then pretending might be something we have to do to avoid being underestimated by a handful of successful people. My personal experience is when I met up with old friends at an event, they were much wealthier than me because they inherited money from their parents, so they considered themselves more successful than me. Then they belittled me by saying that I would never be able to develop like them. Although their words sounded gentle, the impact was very piercing because I felt belittled.