What's something you are really into right now?

What life event did you learn the most from? Would you change it?

Does your current job challenge you to grow in the ways you truly want? If not, what’s missing?

What self-limiting beliefs do you currently hold?

In what way do you differ most from your best friend? In what way are you most similar?

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

How do you feel about your relationship with your mother?

What is something you hate, that everyone else loves?

Imagine you could instill one habit in your child that they would carry for life. What habit would you choose and why?

What recent mistake taught you the most?

How well do you feel your work aligns with your purpose or identity?

What trait signals to you that someone is wise?

How do you reconcile the need for financial stability with the desire to pursue a passion that might be less lucrative?

Do you feel like you've found "your people" yet in life?

Which of your expectations of someone is causing hurt?

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

How has your perspective on your career changed over time?

What's something you've recently let go of, and how has it impacted you?

What's something that you wish was easier for you?

What's a deep question you often ask yourself?

What's one interesting thing you've been thinking about lately?

What's your secret talent that no one would expect you to have?

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

What fictional character do you most relate to?

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

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

What character traits do you most appreciate in your teammates?

What's a current trend you find concerning?

What quality do you most appreciate about your partner?

What aspects of how you were raised do you want to continue on to future generations? What aspects do you want to be sure not to repeat?

What are 3 things you love about yourself?

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

How do you prioritize your goals and desires in life?

What areas of personal development do you feel you need to focus on to to achieve further professional success?

What are you grateful for lately?

What is something you've become increasingly interested in the more you've learned about it over time?

What's one thing that you wish would never happen to you?

How do you feel about your relationship with your father?

Which form of self-expression has become increasingly important to you?

What’s something that made you laugh recently?

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

What was a pivotal moment in your career that led you to where you are now?

If you were a pizza topping, what would you be and why?

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

Are you closer to one of your parents than the other, and why?

What movie traumatized you as a kid?

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

Are there any inner thoughts you have that bother you?

What crucial boundary do you need to establish with someone in your life? What's been holding you back?

What person in your life do you most admire?

What's a challenge you've overcome that made you a stronger person?

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

What's the weirdest food combination you actually enjoy?

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

Can you share a personal tradition that holds deep meaning for you, and explain its origin?

How do you approach networking, and have you had any success stories?

What was the last fear you overcame and how?

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

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

Some historical figures have epithets attached to their names (e.g. Alexandar The Great, or Michael Jackson: King of Pop). What would you like yours to be?

In what ways do you mentor or support others in your field?

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

What would you most like to become famous for?

What was the scariest moment of your life thus far?

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

What advice would you give to your teenage self?

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

What are you most grateful for in your life right now?

Who in your life would you trust with your deepest secret?

Do you feel you're operating in a sustainable way?

What gives you supreme joy right now?

What's your favorite personality or character trait about yourself?

What's one of your biggest pet peeves?

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

Spiritually, do you believe in something bigger than yourself? What inspired this belief?

You will be granted supernatural ability in one of your five sense (sight, smell, taste, hearing). Which would you choose, and why?

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

What inaction or missed opportunity do you regret?

What's something you wish people asked you about more often?

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

Who here is most likely to bring an axe to a pillow fight?

What's the one thing you would like to change about yourself?

What's the most significant risk you've ever taken, and how did it turn out?

What's something you'd like to do, but have a hard time acting on?

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

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

What is one your core principles in life that is guiding you at this time?

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

In what ways are you similar to your parents? In what ways are you different?

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

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

Which societal norm would you like to see ended, and why? What changes would you propose?

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

What have you been eating lots of lately?

How have you stepped out of your comfort zone recently?

What's a compliment you recently received?

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

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

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

What's a belief you held strongly that you changed your mind about?