Know Thyself (and Others)

What is your most cherished childhood memory?
What achievement(s) in your life are you most proud of and why?
Describe a time when the idea of doing something terrified you, but you did it anyway. Why did you do it?
What’s a skill you have that not many people know about?
What’s something you’re nostalgic for?
What is your personal motto?
If you wrote a memoir, what would it be titled?
Do you own any family heirlooms? If so, what’s the story behind it?
Are you more like your father or your mother?
How much do you know about your ancestors? Do you have any stories about them?
What’s the best part about your day-to-day life?
What’s something you’ve been waiting for for a long time?
Who is the most influential person in your life?
Describe an opinion you used to hold but no longer do. What changed your mind?
What are you looking forward to most in your life right now?
What’s the most beautiful thing you’ve ever seen? How do you define beauty?
What do you do when things don’t turn out the way you planned?
What celebrity do you most look up to (if any)?
What traditions in your family do you want to pass on to future generations and why?
Who’s the wisest person you know?

Questions From Literature, Film, and Famous People

Willa Cather wrote in her novel “O Pioneers!” that the only way to really help someone is to understand them. Do you think that’s true? What does it mean to truly understand someone?
In Jane Austen’s novel “Emma,” one of the characters says, “There is one thing, Emma, which a man can always do if he chooses, and that is his duty; not by maneuvering and finessing, but by vigour and resolution.” Is it always possible to do your duty? How do we know what our duty is?
Choose one of these topics to explore: “Socrates’ own conversation was ever of human matters. Investigating what is pious, what is impious; what is beautiful, what is ugly; what is just, what is unjust; what is prudence, what is madness; what is courage, what is cowardice; what is a state, what is a statesman; what is government and what is a governor—these and others like them, knowledge of which made a gentleman, in his opinion, while ignorance could fairly be called slavishness.” (Xenophon, Memorabilia)
“Even when experts all agree, they may be mistaken” (Bertrand Russell). What’s something you think the experts are wrong about?
Franklin D. Roosevelt famously said, “The only thing we have to fear is fear itself.” Do you think that’s true?
In “The First Circle,” Aleksandr Solzhenitsyn wrote, “You only have power over people as long as you don’t take everything away from them. But when you’ve robbed a man of everything, he’s no longer in your power—he’s free again.” What does he mean by this?
“We need never be ashamed of our tears” (Charles Dickens). When’s the last time you cried?
In “Little Women,” Louisa May Alcott writes, “Be worthy of love and love will come.” Do you think she’s right about that?
“Success is not final, failure is not fatal: It is the courage to continue that counts” (Winston Churchill). Describe a situation where you felt like giving up, but you persevered and eventually were victorious.
What do you make of Shakespeare’s quotation from “As You Like It,” “All the world’s a stage, and all the men and women merely players”?
Has a book or movie ever changed your life? What makes a book or movie life-changing?

The Big Questions

What does it mean to be successful in life?
What makes a home?
What is leisure?
Describe the ideal vacation. As a follow-up, what’s the ulti

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