The questions below I accumulated gradually, over the course of many years, using two criteria:
- Is the question itself inherently illuminating?
- Does the question, even in the asking, tend to make you a better person?
Even the very first question, "What is wisdom?" is very difficult to answer with true depth. I once spent an entire ten-day vacation asking strangers "What is wisdom?" Most of the answers were painfully lame and thin: "knowledge," "expertise," "experience." Not one person mentioned deep understanding of your own nature and how in specific ways your nature may be the same or different from that of other people, the difference between short-term and long-term effects in both individual development and the development of complex situations, the moral and immoral responses of human beings and specific understanding of where such responses lead, or the fundamental issue of the many ways we are tempted to and do lie to ourselves.
I dare you to try to answer any of these questions to a fully convincing extent, even to yourself. Go ahead—give it a shot.
What is wisdom?
What is maturity?
What is "character" exactly?
What does it mean to be a complete person?
How can you improve your own thought processes?
What are your personal ideals, and why? Do you come anywhere close to meeting them?
What proportion of your activity is meaningful? What proportion is meaningless? Why?
What proportion of your activity is conscious? What proportion is unconscious? Why?
Can you imagine yourself as a completely different person? Who could you become, better than you are now?
A task you could complete in only a few days would transform your life all for the better. What is that task?
What is the relationship between meaningful activity and stress?
What would happen if you chose to criticize nothing at all, other than yourself?
If you changed your verbal habits, would that change your mind? If so, how?
What are the conformity pressures in your life? How do they affect you?
What are you lying to yourself about?
What could happen in your life, if only you made the choice?
Why do some people evolve, others remain static, and others devolve?
What is the relationship between suffering and depth of character?
What do you habitually pay attention to? What would happen if you chose otherwise?
What constitutes a truly valid, meaningful apology?
With an ideal diet, no bad habits and optimal exercise, you're still going to die. Now what?
What are you not noticing? What is not occurring to you? What are you not thinking about? What are the implications of all of this?
What is the relationship between comfort, complacency & personal development?
What does friendship mean to you?
Is becoming considered unbecoming? Is that why people avoid it?
Have you ever become insane because you were in a relationship, or part of a group?
Are the stories you tell yourself true? Are you sure? What if those stories aren't true?
Why do people not actually solve their problems?
Is your diet healthy? Are you healthy? Do you care?
We all have selective blindness. Can we become each other's seeing eye dogs?
Is all suffering necessarily bad? Can we distinguish between productive and unproductive suffering?
Are genetics and environment your excuse, or do you have some other excuse?
What are you doing to improve society? What else could you do?
On what basis do you manage your finances? Is there an ethical or moral basis to your financial decisions?
Did you use your time on earth wisely?
Are you unknowingly creating scarcity?
What are your limitations? How can you know?
How much of your behavior is robotic? How do you know?
Clichés have stolen your brain. How can you get it back?
What is "spirituality" exactly, and why should you care?
What exactly is virtue, and why is there so little of it?
Are groups of human beings beyond a certain numeric threshold inherently immoral?
What are the sources of evil?
Is there a cyborg in your future? Could that cyborg be you?
External travel versus internal travel: Which is more productive?
Does true art have any future at all?
Is there any such thing as rationality?
You are so much more than what you eat. But what?
What's the point of being religious, if you're not good?
What constitutes "success" to you? Are you getting there?
Emotional competence & emotional incompetence: The most important determinant of success?
Why are so many supposedly spiritual people so horribly impersonal?
Sociopathy as normality: Is conscience just a comforting myth?
Given that there are now far more people on earth, why are there far fewer geniuses?
Personal loyalty versus moral principle: Which side are you on?
Is Freudian theory full of crap, or is it just you?
Do people become "spiritual" because they have trouble with reality?
Does the word "sacred" have any useful meaning at all?
Are you a robot? If so, would you be interested in meeting other robots?
Is the multilingual mind inherently different than the monolingual mind?
What is the good of integrity, if it doesn't actually exist?
Why are post-menopausal women so much more interesting than post-manopausal men?
Would the earth be better off without people?
Is there actually any such thing as gender?
Clearly there are more than just two sexes. So how many are there, and what are they?
What would be an ideal education system?
What exactly does it mean to be a good person?
People are gross, so let's become something better than people. What would that be?
Are we entertaining ourselves into utter idiocy? Is there any solution to this?
Is there any such thing as morality?
Do your emotions control even what you are aware of?
Is every desire for something material actually only a desire for an emotion?
Does the prevention of genius depend on social pressure?
What is the relationship between peace and justice?