Blog

Tired of small talk? Here are 30 questions to spark a meaningful conversation:

• 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?