Of just two skills Tim Ferriss claims are necessary for success, one of those is asking great questions.
The quote from Peter Thiel that Tim mentions above is laid out in more detail in Tools of Titans:
If you go back 20 or 25 years, I wish I would have known that there was no need to wait…
So if you’re planning to do something with your life, if you have a 10-year plan of how to get there, you should ask: Why can’t you do this in 6 months? Sometimes, you have to actually go through the complex, 10-year trajectory. But it’s at least worth asking whether that’s the story you’re telling yourself, or whether that’s the reality.
A good question is often specific to your situation.
For my situation this year, a good question is the following:
“What would I do if it was guaranteed that no matter what, I would make no progress at all in the next 6 months?”
That question works for me because I am very partial to grandiose fantasies of some big success that’s always just around the corner.
As I’ve grown older, the time frame has gradually lengthened, but not nearly enough. It takes time to do meaningful things, and my childish labrador-brain refuses to accept it. The “no progress” question forces me into a brief moment of maturity. It reminds me also to spend my time on things I will be happy to do for their own sake, not just as a means to an end.
The question probably should be
“What would I do if I were guaranteed to make no progress at all this year?”
But I find that prospect just a little too terrifying to entertain…