Ten Infrequently Asked Questions

Notice that some of these questions are abstract, while others are concrete. Some express deep longings, while others are more like spontaneous interests. Many are questions about how to live a better life, while a few are focused on how to succeed professionally. The key to this exercise is to make them open-ended questions that don’t necessarily

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Big questions interrupt the daily routines people fall into and prompt them to step back and see their life from a distance. Here are some of my favorite questions that do that: “What crossroads are you at?” At any moment, most of us are in the middle of some transition. The question helps people focus on theirs. “What would you do if you weren’t a

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Here are a few somewhat more unusual questions we recommend—again, depending on context—with more questions coming in the section on how to get “meta”: “What are ten words your spouse or partner or friend would use to describe you?” “What’s the most courageous thing you’ve done?” “If you joined us and then in three to six months you were no longer

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“What are ten words your spouse or partner or friend would use to describe you?” “What’s the most courageous thing you’ve done?” “If you joined us and then in three to six months you were no longer here, why would that be?” Or ask the same question about five years down the line as well and see how the two answers differ. “What did you like to do a

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Questions I like to ask myself include:-‘What is the most capable version of me that I can imagine?’-‘What would I be like/spend my time doing if all my current major problems had been solved?’-‘What are the things I say I value but don’t act as if I value, and what would my life feel like on inside if I actually acted as if I valued those things?’... See more