What past compromises do you refuse to make now?

What's a personal value or belief you've been reflecting on?

What fictional character do you most relate to?

What's one thing you do to distract yourself that you think you should less of?

If you had to get a tail, what tail would you want and what would you use it for?

Do you love yourself? What does that look like?

What talent of yours do you consider to be inherent, like an advantage you were born with?

What are people surprised to learn you're really good at?

If you were perpetually surrounded by one aroma (asides your own, natural scent) which you and everyone around you could smell, what would it be?

What was the last fear you overcame and how?

If you could change one thing about your childhood, what would it be?

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

Is there anything you think the previous generation did better than your generation?

Who had the most significant impact on your career and why?

Have you ever had a mentor, and what was the most important thing they taught you?

What thoughts distract you when you’re trying to get to sleep?

What's your favorite article of clothing you own?

What's your philosophy in life?

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

When you think of the legacy you want to leave, does your current job contribute to that vision?

If you could choose one superpower, but it had to be extremely specific and unusual, what would it be?

Can you share a personal goal that you haven't achieved yet and why it's important to you?

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

What's the most likely cause for the end of humanity, and how do we stop it?

If you have siblings, how do you (or did you) quarrel with them?

What's something you admire about each person here?

If you had the power of perfect memory recall, what’s the first memory you’d revisit?

What's that one thing you keep buying or doing even though you know it's unhealthy?

If you could teach someone just one thing about how to be in a good relationship, what would it be?

What or who do you have an unhealthy relationship with?

What was your worst conflict with a partner and what happened? What'd you learn from the experience?

What's a funny or embarrassing moment you’ve had at work?

What's a book or podcast you'd recommend that’s related to your career?

What is something that's easy for you but seems difficult for most other people?

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

What do you think is your biggest strength and your biggest weakness?

How do you prioritize your goals and desires in life?

What's the most enjoyable project you've worked on recently?

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

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's your favorite smell?

What's your favorite way to relax these days?

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

If you had 9 lives, what would you do with them?

What do you wish people would stop talking about right now?

Which is more important, nature or nurture?

What's something that tends to ruin your day as of late?

What's something you're embarrassed to admit you enjoy?

What color describes your mood today?

What's the most useless thing you've ever been taught in school?

It's "Freaky Friday". You wake up in someone else's body for a day. Who would you like to wake up us, and have them inhabit your body instead?

What would you like to thank yourself for right now?

What's something that will make you smile every time?

Who here is is most likely to eat cat food?

What's a recent decision you're glad you made?

Who here is most likely to invent the next technology that'll save the planet?

What do you take for granted?

What's a habit you picked up as a child that you wish you hadn't?

What do you think is the most significant impact individuals can make in the world today?

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

What life experience has shaped you the most, and in what way?

When do you feel most helpful to others?

What's your biggest dream?

Which of your expectations of someone is causing hurt?

Which superpower would you pick to subtly make your everyday life easier?

Who here is most likely to dedicate their life trying to go to another planet?

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

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

If you had to skip on meal every day for the rest of your life, which meal would it be?

Who do you go to for advice, and why?

If you had $1M, but couldn’t spend a penny of it on yourself, what would you spend it on?

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

What's one thing you've never done but feels like it's something you need to do in your lifetime?

What's an ethical dilemma that keeps you up at night?

What are some of your recent highlights and lowlights?

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

What's one thing about you that hasn't changed in the last 10 years?

What is the dumbest but most innocent thing you believed as a child?

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

What’s something at the top of your to-do list?

What's the most important life lesson you've learned in the last 10 years?

Who helped you recently?

You can know when you die or how you die. Which do you choose?

What area in your life do you feel you’re making progress? Not making progress?

What's a fun project you've worked on recently?

What's something you're you proud of, but never have an excuse to talk about?

What's a major life decision you made that you're really happy about?

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

What’s your best tip for staying focused and productive?

Who here is is most likely to call in sick at work just to travel for a concert in another state?

What's a deep or difficult question you've been pondering lately?

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

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

What's a deep question you often ask yourself?

What character traits do you most appreciate in your teammates?

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

What inaction or missed opportunity do you regret?

What does 'living authentically' mean to you, and how do you practice it in your daily life?

Which superhero’s powers do you feel are underestimated?

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