What’s your most cherished family tradition? Why is it important?
What have you liked best about your life so far? What’s your happiest or proudest moment?
What do you feel have been the important successes in your life? The frustrations?
What’s the most difficult thing that ever happened to you? How did you deal with it?
What do you think the turning points have been in your life? What were you like then?
Are there times of your life that you remember more vividly than others? Why?
What have been the most influential experiences in your life?
Describe a person or situation from your childhood that had a profound effect on the way you look at life.
If you were writing the story of your life, how would you divide it into chapters?
What, if anything, would you have done differently in your life?
What do you know now that you wish you’d known when you were young?
What have you thrown away in your life that you wish you hadn’t? What have you held on to that’s important and why is it important? What “junk” have you held on to and why?
Over time, how have you changed the way you look at life/people?
What advice did your grandparents or parents give you that you remember best?
Do you have a philosophy of life? What’s your best piece of advice for living? If a young person came to you asking what’s the most important thing for living a good life, what would you say?
How do you define a “good life” or a “successful life”?
Do you think a person needs to first overcome serious setbacks or challenges to be truly successful?
In what way is it important to know your limitations in your life or career?
If you had the power to solve one and only one problem in the world, what would it be and why?
What do you see as your place or purpose in life? How did you come to that conclusion?
What would you like your children and grandchildren to remember about you?
If you could write a message to each of your children and grandchildren and put it in a time capsule for them to read 20 years from now, what would you write to each?