When talking with people, ask deep open-ended questions — like “What’s your biggest regret?” — that will lead to unexpected stories. When ordering in… - Derek Sivers

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When talking with people, ask deep open-ended questions — like “What’s your biggest regret?” — that will lead to unexpected stories.
When ordering in a restaurant, ask them to surprise you.
When doing creative work, let the random generator make your artistic decisions, shaking up your usual style.

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Additional quotes by Derek Sivers

Let the random generator decide what you do, where you go, and who you meet. It’ll scramble your habits.
It’ll break the myth of causality.
It’ll guide you to see places you’d never ordinarily see, and do what you never would have done.

We want to see the world clearly and know what’s what. But once we’re past the first stage of wisdom, the next stage involves adapting to new changes. We don’t get wise just by adding and adding. We also need to subtract.

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