How much is enough?
What are you grateful for?
What setbacks have you endured?
What accomplishments are you proudest of?
What’s a long-term goal you are working towards?
What dreams have you given up on?
What role have mentors played in your life?
How and when have you experienced transcendence?
What do you wish that you’d done differently?
What have you built?
What’s a story you’d like to tell?
In what ways would your college-age self be surprised by who you’ve become?
If money were taken care of, what would you be doing with your life?
What books have most influenced you?
What did you believe then that you disagree with now?
What help do you need?
What role has luck played?
What events have been most influential in your life?
What’s the contribution you seek to make in the world?
What are you currently most excited about?
When have you most felt a sense of belonging?
What has been your experience of loneliness?
What makes you come alive?
What for you would make an ideal day?
How would you define a rich life?
What brings you joy?
What do you worry about the most?
What habits have you recently changed?
In what ways do you fear that you fall short as a parent?
What is holding you back?
