The quality of your questions determines the quality of your life
Are you asking the right questions?
For the longest time, I had been quite skeptical of Tony Robbins. His books dotted the self-help section in bookstores, his face plastered across the cover of each book, with overdramatized and farfetched titles like "Awaken the Giant Within" or "Unlimited Power." People who talked about him spoke of him in reverent tones, going as far to declare him as a "guru."1
Then I listened to a podcast between him and Tim Ferriss which forced me to reconsider my notions of him. It revealed a man who seemed to genuinely care about helping other people achieve their potential. It piqued my curiosity enough for me to learn more about his work and teaching.
Fundamentally, I would say that much of Tony Robbins' "magic" is his realization that patterns of movement can cascade into accomplishments. A change in physical state (e.g. through exercise) or change in perspective can jumpstart changes in emotion, and through repetition, emotions create habits, which cascade into positive changes. He's figured out interesting ways to generate positive feedback loops that help people, all of which stem from an initial change in physical state or perspective.
On changing perspective, Tony Robbins said something that will always stick with me:
The quality of your questions determines the quality of your life.
Alan Kay said that a shift in perspective is worth at least 80 extra IQ points, and I believe it is asking better questions that allow us this perspective shift. In reality, intelligence is less IQ and more "will to think," where those who demonstrate a greater curiosity and epistemic humility often end up ahead.
The point remains that our questions constrain our understanding of reality and what is possible. Questions (and their answers) compound into more questions and more answers, allowing us to explore and learn more in iterations of learning.
Ever since stumbling upon this idea, I've been striving to always ask more questions.2 I've spent time collecting questions that I've found to be useful in multiple contexts for spurring orthogonal thinking and/or deeper reflection, and here are some of them:
Given that I hold position x, what evidence would I have to see to change my mind?
What is the most portable concept from your field that you think is undervalued and applicable to other fields and practitioners?
from Sam Altman: Is this person a force of nature? And what can I learn from them?
from Tim Ferriss: Who is good at this despite being poorly built for it? Who is good at this who theoretically shouldn’t be?
from Eliezer Yudkowsky: "If you were a character in a book, what would your readers be yelling at you to do?"
What are some quality, general-purpose questions that you like to ask?3
I always get nervous whenever someone invokes the "guru" moniker, as it tends to suggest a replacement of your own will, thinking, and agency with whatever is being fed to you by said "guru."
I subscribe to the quantity creates quality theory, so more generated questions means that I'll end up with a larger number of good questions.
I'd be remiss if I didn't include Morgan Housel's excellent list of questions: https://www.collaborativefund.com/blog/i-have-a-few-questions/