What's a truth you've recently come to terms with?

What's your favorite memory with your family?

If you could only use five words, how would you describe yourself?

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

Have you picked up any new skills at your job this year?

What do people think is hard but actually isnt?

If you could promote one value or ethic in the world, what would it be and why do you think it's vital?

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

Explain your current feelings in life to a 3 year old.

What is the last book you read? Would you recommend it?

What's one thing you recently did for yourself?

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

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

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

What profession would you be in if you had known about it earlier?

What do you wish people would ask you more about right now?

What do you plan to learn in the coming days?

What behavior or trait immediately makes you like someone?

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

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

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

What's the most challenging ethical dilemma you've faced in your career?

What do you think people might envy you for?

What was your favorite childhood toy?

What is your most regretful purchase?

If you could start your own charity, what would it focus on?

You can stop time for 24 hours. What do you do with this opportunity?

What are you working on in your relationships (with friends or with a partner) right now?

What's a challenge you recently faced?

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

What trait signals to you that someone is wise?

What is your biggest accomplishment outside of academia and work?

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

Is there an experience you think everyone should have at least once in their lives?

What would you consider to be a 'dream job', and how close is your current job to that ideal?

Is there a particular event or moment that redirected the course of your life? How did it impact you?

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

What's a new hobby or activity you've tried recently?

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

What do you consider as red flags in a potential employer or boss?

What do you wish people would talk more about right now?

Have you ever turned down an opportunity, then came to later regret that decision?

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

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

If every time you snapped your fingers, you would instantly and irreversibly be transported to a random point in humanity's timeline, would you snap your fingers? If so, how often?

Have any priorities recently shifted to the forefront of your life?

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

What's the most exciting improvement you've been seeing in yourself recently?

Which best describes you? An introvert or an extrovert?

What legacy do you hope to leave as a result of your professional work?

What's a hobby you've always wanted to try?

What or who do you have an unhealthy relationship with?

What professional accomplishment are you most proud of and why?

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

How is your current health, fitness, or wellness routine going?

What would make you feel like "you made it"?

What do you most need to hear right now, and from whom?

What does your ideal/dream life look like?

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

Think of one of your big, lofty goals. What small step could you take today towards achieving it?

What tools or apps do you find indispensable for your work?

In what way do you differ most from your romantic partner? In what way are you most similar?

What recent mistake taught you the most?

Are human desires endless, and can a society exist without wanting more?

If you could be the CEO of any company, what company would you choose?

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

Have you ever made a dramatic career shift, and what drove that decision?

What made you happy today?

What song has been on repeat for you lately? Does it have any special meaning?

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

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

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

If you could travel anywhere in the world right now, where would you go and why?

What quality are you currently cultivating in yourself?

Where you currently facing uncertainty or unknown, and how are you navigating it?

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

How has your perspective on the world changed in the last five years?

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

What’s one family tradition you want to pass down to your kids?

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

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

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

What kind of person do you want to be?

What practice or habit (if anything) best supports your mental health/well-being?

What’s your dream vacation right now? Why?

If you could intervene during any historic event, changing history, what would it be? How would things unfold differently?

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

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

What has surprised you recently?

If you were a dictator of a small country, what crazy dictator things would you do?

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

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

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

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

What's a standout moment where you felt excited recently?

What's something you're absolutely convinced is going to happen in the future?

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

How do you balance work and personal life?

What's a funny or interesting story from your week?

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