Think of a time you were deeply satisfied at work. What specifically made it satisfying?
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Think of a time you were miserable at work. What specifically made it intolerable?
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When you've changed jobs or roles, what was the real reason?
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If you had to choose between more money with less freedom, or less money with more freedom, which would you pick? Why?
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What would you refuse to give up in a job, even for a significant promotion?
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When you daydream about ideal work, what does a typical day look like? Be specific.
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