A More Beautiful Question By Warren Berger

• To ask a powerful question, we must:

Step back.

Notice what others miss.

Challenge assumptions (including your own).

Gain a deeper understanding of the situation or problem at hand, through contextual inquiry.

Question the questions were asking.

Take ownership of a particular question. 

• To question well, you must have the ability to say, ‘It doesn’t have to be that way.‘

• You don’t just “find” answers to complex life problems. You work your way, gradually, towards figuring out those answers, relying on questions each step of the way.

• The illusion that an “answer” is out there if we can just find it extends to everything from the dream job to larger concepts such as happiness or purpose. Creating happiness is ongoing. You don’t find it, you gradually figure it out for yourself—questioning and experimenting as you try to understand what makes you feel happy and how to bring more of that into your everyday life. 

• Figuring out what you want to accomplish is a continual search—and questions are the means to the search. 

• If not now, then when? If not me, then who?

• It’s easier to act your way into a new way of thinking then to think your way into a new way of acting.

• The challenge is not just to think of questions, but to then think about those questions—culling the best ones, improving them, and figuring out how you might begin to act on them. 

• What sets apart the innovative questioners is their ability—mostly born out of persistence and determination — to give form to their ideas and make them real. 

• The key to adopting this manner of questioning is to make an effort to become “detached”— from everyday thoughts, distractions, preconceive notion‘s, habitual behaviors, and even oneself. Basically, you begin to observe yourself as if you were a third-party. If you could achieve that sense of detachment, your thinking becomes more flexible and fluid and you find yourself in a better position to question everything. 

• “The mind of the beginner is empty, free of the habits of the expert. Such a mind is open to all possibilities and can see things as they are. In the beginners mind there are many possibilities, but in the experts there are few.” -Shunryu Suzuki

• It all starts with slowing down, stepping back, and trying to shift perspective in order to see your own life—and the problems, opportunities, and challenges with tackling—more clearly.

• What matters is your ability to triangulate, to look at something from multiple sources, and construct your own warrants for what you choose to believe.

• Drawing on other peoples experience resources is often better than going at it alone. When looking at challenging problems or questions, the more perspectives that can be brought to bear, the better. 

• If you give the mind time and space, it will do its own work on the problem, overtime, and it will usually come up with interesting possibilities to work with. 

• By living with a question, thinking about it and then stepping away from it, allowing it to marinate, you give your brain a chance to come up with the kinds of fresh insight and what if possibilities that can lead to breakthroughs.

• Fear is the enemy of curiosity.

• If you don’t have that disposition to question, you’re going to fear change. But if you’re comfortable questioning, experimenting, connecting things – then change is something that becomes an adventure and if you can see it as an adventure, then you’re off and running. 

• If you seek out problems in your life before they’re obvious, before they have reached a crisis stage, you can catch and address them while they still offer the best opportunities for improvement and reinvention.

• “The trick is to go from one failure to another, with no loss of enthusiasm.” -Winston Churchill

• When analyzing a misstep, you should ask, in this failure, what went right? Conversely, when you try out something that seems to have succeeded, look for what went wrong or could have been better. The best learning comes from looking at successes and failures side-by-side.

• Failure is, in a sense, the highway to success, inasmuch as every discovery of what is false leads us to seek earnestly after what is true.

• If you dream of something worth doing and then simply go to work on it . . . if you think of, detail by detail, what you have to do next, it is a wonderful dream even if the end is a long way off, for there are about five thousand steps to be taken before we realize it; and start making the first ten, and stay making twenty after, it is amazing how quickly you get through those five thousand steps.

• One good question can give rise to several layers of answers, can inspire decades-long searches for solutions, can generate whole new fields of inquiry, and can prompt change inch in entrenched thinking. Answers, on the other hand, often end the process.

• “Climb the mountain now to plant your flag, but to embrace the challenge, enjoy the air, and behold the view. Climb it so you can see the world, not so the world can see you.” -David McCullough

• “Don’t just teach your children to read. Teach them to question what they read. Teach them to question everything.”

• “Computers are useless— they only give you answers.” -Picasso

• Five habits of mind:

1. EVIDENCE: how do we know what’s true or false? What evidence counts?

2. VIEWPOINT: how might this look if we stepped into other shoes, or looked at it from a different direction?

3. CONNECTION: Is there a pattern? Have we seen something like this before?

4. CONJECTURE: what if it were different?

5. RELEVANCE: why does this matter?

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