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

Complete this sentence: "I wish I had someone with whom I could share ... "

What's a challenge you recently faced?

What's a recent disagreement or conflict you had in the workplace? How did you handle it?

When was the last time you experienced stillness and wonder?

What's been on your mind a lot lately?

Who here is most likely become a philanthropist?

How do you prioritize your tasks when everything seems urgent?

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

What do you find yourself fantasizing about these days?

What do you believe is the most significant factor in shaping one's destiny, and how much control does one have over it?

You can only guarantee your child learns one life principle. What do you teach them?

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

What's a recent personal growth moment you've experienced?

If you were to suddenly inexplicably go missing, who in your life would be most likely to solve the mystery and find you?

If you could pick up a new skill in an instant, what would it be?

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

What are some of your recent highlights and lowlights?

What was your biggest win lately?

What's a significant change you're considering or have made?

How do you contribute to a positive work environment or culture?

What subject or course do you wish they had offered in school?

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

What do you consider as red flags in a potential romantic relationship?

What did you learn about the concept of love from your parents? Is there anything you want to keep, or anything you want to let go?

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

What is something you love, that everyone else hates?

Who in your life do feel is receptive to receiving feedback?

What's the most fun you recently had? What did you do, and who were you with?

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

If you could go back and relive one day in your life without changing anything about it, which day would you choose?

What's something people often incorrectly assume about you?

What's your most common feeling lately?

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

Are you settling for less than what you are worth? If so, why?

What's the best purchase you recently made?

Explain your job to a 3 year old.

What kind of person do you want to be?

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

Who helped you recently?

Is there anyone close in your life that perceives you differently than you perceive yourself?

What's your favorite way to unwind after a busy week?

How do you feel about your relationship with your father?

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

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

What bad habits would you like to get rid of? What steps do you need to take to make that happen?

What's your ideal first date?

What was your first job ever?

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

What skills or passions are you not currently utilizing in your job?

How has your industry changed since you started your career?

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

To what degree do you modify your behavior based on who you're with? Do you think this is good or bad?

What do you have up in your browser tabs right now?

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

What was the best birthday gift you ever got?

What do you plan to learn in the coming days?

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

How has your perspective on your career changed over time?

Which is more important, nature or nurture?

A highly advanced alien species has arrived on Earth, and you are selected as the spokesperson to represent humanity. You have one sentence to communicate your most important message. What do you say?

If you could instantly bankrupt any person, company, country, or organization, who would it be?

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

What instantly makes you think less of someone?

Are you currently holding a grudge against anyone?

What's a surprising hobby you enjoy?

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

When do you feel most helpful to others?

Think of someone you're currently in conflict with. If it was the last conversation you'd ever have with them, what would you say?

What or who do you have an unhealthy relationship with?

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

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

What's one rule you'd put in place if you ruled the world for a day?

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

If you only had one year left to live, what would you do?

Have any failures played a significant role in your your career development?

What are some bad things you did as a teenager?

Who here is would most likely become a CEO at a company ranked amongst the top 100 largest in the world?

What’s your take on the common career advice to "follow your passion"?

What's a recent moment in which you're proud that you spoke up?

What's a time when you were extremely underprepared for the task or situation at hand?

What social behaviors of yours are driven by the need for safety, belonging, acceptance, or validation, rather than genuine desire?

If you could witness any event in the future, what would you choose to see?

What career decisions have you made based on fear? What decisions have been based on confidence?

What is one action that would make today a success?

How authentically do you feel you represent yourself to others?

Are there any relationships in your life that feel imbalanced? What would it look like to restore balance?

How do you stay productive and motivated when working from home?

How have you stepped out of your comfort zone recently?

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

What behaviors will you no longer accept in your relationships?

Have you ever desired or longed for something, but once you got it, discovered it was overrated or that you no longer wanted it?

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

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

On a scale of 1-10, how happy are you?

How much of your decision to stay in your current job is influenced by comfort and fear versus ambition and fulfillment?

What's a habit you're trying to develop or break?

You just inherited $10,000,000. How does your life change tomorrow?

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

If you could know for certain the answer to any question, what would that question be?