Is there anything you think your generation does better than the next generation?

What stopped you from following, or encouraged you to follow, your childhood passion?

What was your most memorable moment with your parent(s)?

What's a goal or project you've made progress on?

In three words, how would your family and friends describe you?

If you could live in any movie universe for a week, which one would you pick?

If you could have a superpower that helps you in your current job, what would it be?

What do you consider as red flags in a potential employee or coworker?

You're gifted 24 hours where you and your pet(s) are suddenly able to talk to each other. What would you want to tell them, and how would you want to spend your time with them?

What's the most important lesson a friend has taught you?

What do you think people might envy you for?

What have you been dreaming of eating lately?

Which is more important, nature or nurture?

What trends do you foresee in your industry in the next five years?

How do you feel about your relationship with your father?

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

You can impart one understanding about human relationships to your child. What insight do you choose to share?

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

What do you feel like you’re really good at?

What is your best season of the year? Why?

What are your biggest goals between now and the next issue of our Letterloop?

If the last month were a chapter of your life, what would you title it?

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

What are some bad things you did as a teenager?

You can guarantee that your child will have a deep understanding of one event in history. Which event do you choose and why?

What's your favorite memory with your family?

Are there any inner thoughts you have that bother you?

How can you better help others succeed, especially those who often go unnoticed?

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

Who do you wish was still alive? Could be someone you've met, never met, anyone.

Name one thing that stresses you out without fail.

What's something you did recently that took courage?

What would people be surprised to learn you spend a lot of time on at work?

Do you have a best year of your life? A worst?

What do you find yourself fantasizing about these days?

What outfit makes you feel powerful, smart, or capable?

If you had a magic wand, how would your life magically be better a month from now?

What do you think is the best place or way to meet a signifcant other?

After death, you can roam the universe and observe anything you want for all eternity, but never interact with anyone or anything. Or, you can cease to exist. Which would you choose?

What is your why? What gets you up in the morning?

What activity absorbs you completely and makes you lose track of time?

What boundary did you recently set that has improved your relationship with someone?

What do you think happens after we die, if anything?

What's something you've achieved that you never thought possible for yourself?

What has surprised you recently?

If you could be invisible, but it would mean being permanently invisible, would you want to be this way?

Do you have an inner monologue? Do you think your thoughts in words or concepts?

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

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

What scientific or technological advance blows your mind?

What’s one of your earliest memories of earning money?

What's something you're looking forward to doing or experiencing?

If all animals were the same size, what would win in a fight?

Would you rather have the power to turn invisible or to read minds?

What was the most recent thing that made you cry?

If you could learn one secret from anyone, who would it be and what would it pertain to?

When have you felt the most connected to something greater than yourself, and what were the circumstances?

What’s one thing that brings you energy and joy lately?

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

Is there anything important you've been putting off? If so, why?

What's the most challenging thing you're working through these days?

What would you do if there were no internet for the next 24 hours?

What principle do you hold that you would never compromise on, even under pressure?

Is there anything you'd like to get off your chest?

What's your philosophy in life?

Which relationships are you investing the most in right now?

What's an interesting conversation you recently had?

What do you consider as red flags in a potential friendship?

What fictional character would you most like to have as a mentor?

What's a professional setback or shortfall you recently experienced, and how has it influenced you?

If you accomplished something major, who is the first person you'd tell and how do you think they'd react?

What's something very strange that happened to you?

How's your family doing?

What did you learn about yourself from your last relationship?

If you could choose one experience from your life that your child could also have, what would it be?

Has your gut feeling or intuition about someone or something ever been wrong?

Imagine that you can choose when and how you die. How long would you like to live, and how would you like to go?

Is there anyone who intimidates you? Why do you think this is?

What's the best advice you've ever received?

What does "success" mean to you, and how has that definition evolved over time?

What's the most unusual food you've ever tried, and would you eat it again?

How’s your heart today?

Are you currently mentoring anyone, or being mentored? How is that going?

What's a surprising hobby you enjoy?

What's a moment in your life that felt like a crossroads?

What's your go-to productivity hack?

What's a great piece of advice you recently received? Who was it from?

What elements of your daily routine have become non-negotiable lately?

Is there a quote or saying you call to mind often, intentionally or unintentionally?

If you could telepathically say something that all 8+ billion people on Earth could hear at once, what would it be?

What was your first job, and what did it teach you?

What inaction or missed opportunity do you regret?

What was the scariest moment of your life thus far?

What was your first job ever?

Are you currently holding a grudge against anyone?

What's the most valuable lesson you've learned from a culture different from your own?

What's a fear or insecurity you're working through?

What kind of games did you play as a child?

What's a memorable lesson you've learned from a mistake you've made?

What do you think will still be the same about you 10 years from now?