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Questions are powerful insight generators.

Questions invite curiosity and discovery.

Questions are a way to improve your self reflection.

Questions are a way to deepen intimacy and knowledge of another.

Asking someone thoughtful questions shows you respect them.

Questions, by the way they are framed, can be unhelpful or limiting, or they can be powerful and liberating.

Most people ask far too few questions driven by curiosity and the joy of discovery.

You can create a list of your favorite questions. This list could either be a list of questions you ask to get to know someone better, or they could be a list of questions about big ideas and projects you are working on. My 12 favorite questions is an example of the latter.

Referenced in


This whole experiment is inspired in part because I want to keep learning and growing, and I don't want to only share work with the world when it's in a completely finished state. The further I progress in my career and success, the more I'm tempted to appear as if I have it all together. I don't. I have many blind spots, thoughts in progress, and I'm constantly asking questions as I continue to learn. I want to grow in my thinking with the rigor that athletes train their bodies. I have thousands of notes in my digital second brain on Roam Research, so I thought I'd share some of those pages here in a bit more disciplined, yet still work-in-progress fashion. If some of my notes don't feel finished or don't totally make sense, that's because they're not finished, or are written largely to develop my own thinking.

Evergreen Notes

They're guided by the questions: "What thinking practices can help me reliably develop insights over time?" and "how can I shepherd my attention effectively?"

What stands out to you?

'What stands out to you?' is one of My 12 favorite questions. I typically ask it multiple times a day. I use this question at the end of most of my therapy sessions. Asking powerful questions has developed into one of my superpowers, and can be learned by anyone.