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Desire success? Start asking dumb questions.

In a world afraid of embarrassment, asking dumb questions is a super power, says Tim Ferriss. It takes a secure intellect to risk looking silly, but the rewards are there for the taking.

Chris Sacca is very good at asking dumb questions, says Tim Ferriss – and Ferriss means it as a compliment. Years ago, Sacca got an entry-level job at Google and invited himself along to executive meetings where, once people got used to his strange presence, he started asking dumb questions, chiming in with the obvious things that no one was bringing up. "He's created some incredible breakthroughs in investing as a result of that," says Ferriss. In a world where everyone is afraid of looking stupid, a lot of basic improvements and ideas get missed for fear of embarrassment. Through several anecdotes amassed during the writing of his new book Tools of Titans, Ferriss makes a case for being more intellectually secure in yourself so that you can raise your hand without fear, ask a dumb question, and actually become smarter. And in Sacca's case, wealthier. Tim Ferriss is the author of Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers.

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Entrepreneurs: Stop Fetishizing Failure, Start Asking Absurd Questions

Silicon Valley's entrepreneurial trends go through births and deaths, revolutionizing business attitudes before turning stale. Tim Ferris explains two trends: one near its death, the other very much alive and kicking.

There are two start-up trends that are sweeping Silicon Valley and beyond: one, says Tim Ferriss, needs to be redefined, and the other needs to be more widely activated. The first has gained so much popularity it has become a motto: "fail fast, fail forward". Ferriss is concerned that we’re fetishizing failure as something harmless that only leads upwards, when in reality in some industries it can be quite deadly. The second is the practice of absurd questions. Billionaire investor Peter Thiel will look at a business plan and say to its creator: "Why can't you accomplish your ten-year plan in the next six months?" Asking seemingly crazy questions, and setting hypothetical limits (such as, "how would you hit your goal in the same time by working only 2 hours per week?"), forces divergent thinking and can prompt you to actually do what once seemed unthinkable. Tim Ferriss is the author of Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers.

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Technology & Innovation

Procrastinating? Use these Jedi mind tricks to meet your goals.

Tim Ferriss shares a bounty of strategies to help you really and truly overcome procrastination. And if it doesn't do it for you, hey, at least you just killed 10 minutes.

Procrastination hits everyone, although perhaps that wording is wrong. It’s an internal force rather than an external one that acts on you – and that’s great news because it means getting past the thumb-twiddling is just a matter of having an actionable plan.

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