Writing your stories is, sometimes, simply a matter of answering questions.

That said you’re probably wondering: WHAT questions?

Over the years I’ve helped hundreds of people tell their stories. Everybody, and I mean EV-REEE-BODY, loves the following questions. I call them the “Terrific Twenty.”

Select a question; sit at your keyboard; invite your intuition to speak; don’t think; start to type. Your story will practically write itself. Guaranteed.

  1. What is your first memory or a very early memory?
  2. When you were a kid, what did you want to be when you grew up? How did that turn out?  
  3. Did you have a “road not taken”? What? Do you regret a missed opportunity? Or was that one of your best decisions ever?
  4. Describe a typical family meal when you were growing up. Who sat around the table? Were mealtimes important to you? Why/Why not? What was your favorite meal—dish?
  5.  If you had all the time in the world and money was not object, what would you do? Why?
  6. What was the best gift you ever gave—ever received?
  7. What challenges—obstacles—did you face during the early years of your family business or another career? How did you overcome them? What advice do you have about overcoming obstacles?
  8. Tell me a story about a happy time in your life. Tell me a story about a sad time in your life.
  9. Pretend you are going on a long trip. Where will you go? Why? What will you write on the note you leave behind on the kitchen table?
  10. Tell me a story about your best friend. What do friends mean to you?
  11. Tell me a story about your first date—who was it with, what did you do, and where did you go? Did it end with a goodnight kiss? Why or why not? Who—what—is the true love of your life?
  12. Tell me a secret.
  13. How do you hope you will be remembered?
  14. Today is a perfect day. What will you do?
  15. What is the best piece of business advice you ever received—ever gave? What is the best piece of personal advice you ever received—ever gave?
  16. Tell me a story about your favorite tradition—holiday or otherwise.
  17. When you’re feeling down, what makes you smile?
  18. If you ruled the world, what changes would you make? Why?
  19. Pretend you are creating a time capsule that will be opened 100 years from now. What will you put in it to represent your life and your lifetime? When you look down on the world and your family 100 years from now, what do you hope to see?  
  20. Tell me a story about a time and place you felt truly happy—truly at peace—with yourself and your life. What does happiness—peace—mean to you? Does money itself lead to happiness?