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I like to ask people what their most controversial opinion is. That often leads to interesting talks, and people’s answers can be surprising.
In my experience, the kind of questions I ask people, they back-off from answering them because they’re too personal or deep for us. For example:
– If today was your last day, how would you spend it?
– how do you want to be remembered by the people who matter most to you?
– If you could, what advice would you tell your 15-year-old self?
And some questions are too philosophical. For example:
– what is the reason we are in this world?
– why are we here, and what are we supposed to be doing with our time?
Maybe start simple with questions, then build and get complex. All the best.