What was the hardest decision you've ever made?

How would you summarize your life so far in one sentence?

What is the smallest thing for which you are grateful?

Who has had the most positive impact on your life?

What is your biggest non-academic, non-work-related accomplishment?

If you could use a time machine, would you rather have one that only goes back in time or only goes forward?

Where do you wish you had grown up?

What is something you're terrible at but wish you could do well?

Do you have a personal mantra? If so, what is it?

If you could change one thing about yourself physically, what would you change?

What do you think "success" means? How do you define it in your own life?

What single event or decision do you think most affected the rest of your life?

What would you like to accomplish before the year is over?

What was the best year of your life? The worst?

What is the longest line you have ever waited in? What was it for?

What is something you've done/felt/seen/etc. that you wish you could experience again for the first time?

What fictional character do you most relate to?

What character archetype is closest to your personality?

Have you ever had an epiphany? What was it about, and what sparked the realization?

Is there something about you that people assume because of your appearance or demeanor? What is a trait or preference you have that people don't expect you to have?

What was the happiest moment of your life so far?

What is your ideal birthday? Not the date, but rather your ideal way to spend the day.

What's the worst advice you've ever been given?

What is the best advice you've ever received?

What fact about yourself took you the longest to understand or accept?

In what ways do you benefit the world?

What do you get the most compliments about?

If seasons never changed, which would you most like to live in eternally?

What lesson have you had to learn again and again?

In what way would you most like to become famous?

Are you currently pursuing what makes you happy? Why or why not?

What is the best thing about the place you live?

What is one small change you made in your life that had a much bigger impact than you anticipated?

What has been the most notable phase of your life?

What keeps you up at night?

In what ways are you stubborn?

What is your favorite word and why?

What is a childhood habit or preference that you'll never outgrow?

Which of your flaws are you most proud of?

What's your favorite joke you've ever heard?

What's your favorite article of clothing you own?

What was your favorite thing about the place you grew up?

What was the best opportunity you ever received?

What unpleasant experience are you most proud of yourself for making it through?

What's the best outcome of a complete accident you've experienced in your life?

Have you ever desired or longed for something, but once you got it, discovered it was overrated?

What did you know was a mistake as soon as you decided to do it, and why did you go through with it anyway?

What is something you've done that you recommend everyone do before they die?

What was the scariest moment of your life thus far?

What's something you wish you enjoyed but never can seem to?

What is the greatest physical pain you've ever felt?

What is something you never thought you'd be able to do, until you actually did it?

What's the craziest thing you've ever done?

Have you ever been offered a good opportunity but refused? What was the situation?

What historical event would you most like to have experienced?

When do you feel like the best version of yourself?

What’s something you went through that you wouldn’t wish on your worst enemy?

When was the last time you tried something new? What was it? Did you enjoy it?

If someone were to travel to your town and you could only take them one place, where would you take them?

What is something that gets cooler/more interesting the more you learn about it?

What is the hardest way you’ve learned an important lesson?

What's the best lesson you've learned from a difficult situation?

What is your favorite musical?

What is your favorite movie?

What is your favorite album?

What is your favorite song?

What is your favorite TV show?

What is your favorite podcast?

What is your favorite documentary?

Who is your favorite actor?

Who is your favorite singer?

Who is your favorite band?

Who is your favorite comedian?

What is your favorite movie from your childhood?

What is your favorite TV show from your childhood?

What is your favorite song from your childhood?

What is your favorite singer or band from your childhood?

What is something you don't realize is weird until you really think about it?

What small thing annoys you to an irrational degree?

What always makes you nostalgic?

What is one childhood memory that you remember especially well?

If you could erase one thing or event from your memory, what would you choose?

Is there a song/movie/food/etc. that strongly reminds you of someone whenever you experience it? Who does it remind you of?

Are there any smells that bring back memories for you? What are they, and what memories do they elicit?

What is the most memorable meal you've ever had? (It can be good or bad.) What made it so memorable?

Think of the best teacher you've ever had. What did they teach, and what made them so special?

Think of your biggest regret. If you could go back in time and make a decision to keep it from happening, would you?

When you were a kid, were you excited to be a grownup? What about growing up excited you?

If you got a promotion, a job, a college acceptance, an accolade/award, or just generally accomplished something major, who is the first person you'd tell and how do you think they'd react?

What trait do you admire in others but don't possess yourself?

Is there something you wish everybody knew about you without you having to tell them?

What historical figure do you most admire and why?

Would you prefer your family to be smaller or larger than it is now, or neither? Do you wish you were more involved with your extended family?

If you had the power to completely solve one social or political issue affecting the world today, which would you choose?

If you had the power to completely eradicate one disease, which would you choose to abolish?

If you could play any instrument or learn any language in two hours, which would you choose and how would you use your talent?

Assume you have a lot of musical talent. If you started a band, how many people would be in it and which position would you be? What would you name it? What genre would you play?

If you could ask your future self one thing, what would it be?

If you could be any animal, what would you be and why?

What is the most useless talent or skill you possess? How and why did you learn it?

If you were an inanimate object, what would you be and why?

If you could live in another time period but stay in the same place you live now, when would you want to live?

If you were a character in a movie, book, or television show, what genre would you live in?

What have you been meaning to do but haven't yet done? Why haven't you done it?

What question do you most hate being asked?

What would you title your memoir?

What is the quality you admire the most in the person you dislike the most?

What is the most important quality you look for in a friend? A romantic partner?

What was the most recent thing that made you cry?

What are the books/movies/games that never get old and always make you feel better when you get down?

What is the most trivial thing about which you have a strong opinion?

Some historical figures have epithets attached to their names, like The Mad or The Wise. What would you like yours to be?

You have one year to live: how do you spend it?

What one thing, whether it's something you did or something you made or something you caused to happen, would you like to be remembered by?

What is the closest you've ever come to dying?

Imagine that you could choose when and how you die. At what age would you like to die (no maximum here) and how would you like to go?

You're old and on your deathbed. With your last breath, you may deliver your last words to anyone you know. What do you say and who do say it to?

What cliché do you think is bullshit? What cliché do you think holds truth?

What is your least popular or most controversial opinion?

What has been the biggest change of heart you've had? Have you ever started off on one side of an issue and wound up on the other? What influenced that change?

What, if anything, is too serious to be joked about?

What is the most ordinary-seeming thing that you find fascinating?

What activity makes you lose track of time?

Have you ever challenged or questioned a belief you held for a long time? What prompted it and what was the result?

What's a brief summary of your outlook on life?

Do you believe in fate, the idea that "whatever is meant to happen will happen"? Or do you believe more in a universe governed mainly by chaos and the unknown?

Has a piece of media (book, film, play, song, etc.) ever changed the way you thought about the world?

What do you do differently that allowed you to succeed, that you think other people who had similar circumstances to you did not. Where did you succeed where they didn't?

What moment in your career are you the proudest of?

What trends are you most excited about right now?

What founder or business person inspires you the most?

How do you make your worklife better?

What was the first job you ever had?

What was the most recent job you ever had?

What was the best job you’ve ever had?

What was the worst job you’ve ever had?

What is the weirdest job you’ve ever had?

If you lived in a colonial or Medieval village, what would your job be?

If you could be good at any profession without having to receive the accompanying education or trade experience, which would you choose?

If you’ve had more than one job, which job taught you the most?

What is the one thing you've made that you're the most proud of?

If you opened a business, what type of business would it be? What would you name it?

What is your biggest academic or work-related accomplishment?

Let's say that regardless of what job you have, you'll make $250,000 a year, enough to live comfortably without having to worry about expenses. What job would you choose to have if money were no object?

What's the coolest project you've ever worked on?

Have you ever gotten the giggles in an inappropriate place? Where was it?

What are you most likely to be arrested for (even if you don't do anything illegal—what crime do you think you're most likely to commit)?

Do you have any conspiracy theories? If so, what are they?

What is the "strangest" thing you believe in? Do you believe in the supernatural? Heaven, angels, ghosts? Luck, fate, magic? Mind reading, lizard people, the Illuminati? Where do you draw the line of belief and disbelief?

What do you know isn't real, but want badly for it to exist?

What scientific or technological advance blows your mind? Is there any technology that seems so futuristic and advanced you're surprised it actually exists?

In a "Freaky Friday" situation where you woke up in someone else's body, who would you like to be for a day and have them inhabit your body?

How would you describe this year with a single word?

What's a thing you learned about yourself this year?

What are you most grateful for this year?

What is one difficult decision you’ve made this year?

What are you most excited about for the year to come?

What hasn’t gone as planned this year?

Does your job reflect your core values?

If you can only contact three people for the next entire year, who will they be, and why?

What is the most worthy investment of your time/money this year?

Describe the best day of the year.

What have you done this year to improve your mental health? (therapy, journaling, support group, etc.)

What are you most grateful for this year?

What is something nobody asked you that you wish they would?

What went well in the past week because of you?

What two or three things, your fault or not your fault, changed your professional trajectory?

What's one belief you had as a child that you no longer hold? What changed your mind?

If you had the ability to relive a single day of your life exactly as it happened without changing anything, which day would you choose and why?

Flash forward 3 years, and your company has failed. Why has it failed? What assumption do you think was wrong?

Tell me, when you're sitting around the Thanksgiving table with your family, what you say about your company and your job.

What news source do you wake up to?

Do you have a favorite weekend market?

Papers delivered or a trip down to the kiosk?

A favorite podcast?

What's the best thing you've seen on TV recently?

What about books?

What are your summer plans?

What's the first thing you pack in your suitcase?

What food will you be looking forward to eating?

What's your superpower?

What other career goals do you have?

What types of problems do you like to solve?

What are the last two things you changed your mind about?

If you could have a gigantic billboard anywhere with anything on it, what would it say and why?

What is your one absolutely fundamental contribution that would not happen without you?

If you could press a button and solve one problem of your business, what would it be?

What's been the highlight of your career so far, and were there any deliberate moves you made when you were at my stage that contributed to that highlight?

What are you rethinking right now?

What is ignored or neglected by the media -- but will be studied by historians?

Instead of "What does your company do?" ask someone, "What changes when someone uses your company/product?"

Why did you choose this path at this point in time?

As a kid, what did you want to be when you grew up?

What is your favorite childhood memory?

Who is one person from your life that you admire the most today?

What's the best thing about your hometown?

What is ignored or neglected by the media -- but will be studied by historians?