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Taking Smart Risks: How Sharp Leaders Win When Stakes are High by Doug Sundheim

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CHAPTER ELEVEN

Fail Early, Often, and Smart

Perfectionism is the enemy of creation.—JOHN UPDIKE, American Writer

One of the questions I ask clients who are about to take a risk is: “What are your thoughts on failure?” The question usually garners a nervous chuckle, followed by a response along the lines of: “I don’t like it, and I try to avoid it at all costs.

Wanting to ease my clients’ anxiety, I ask them to reflect on a productive failure—a misstep or difficult situation that turned out to be surprisingly beneficial. Within 30 seconds, most people can usually think of at least one. It’s often a compelling story of a struggle that led to personal development, the development of the person’s business, or both. When I ask whether, given the choice, ...

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