Life is what happens while you are busy making other plans.
John Lennon
Every Wednesday at 10:00, I gather with 10 to 15 similarly aged men for conversation and fellowship. We often start our meeting with the big news of the day, but it doesn’t take much to shift into subjects more personal and relevant to us old(er) guys — grandchildren, medical concerns, home projects gone awry, and aging parents are all common themes. We have lived lives filled with joys, successes, failures, disappointments, and transformations and our conversations are richer because of our shared experiences.
Last week, someone brought up the idea of creating one’s life story and the website storyworth.com was suggested as a tool to accomplish that. If you aren’t familiar with Storyworth, their business model is quite simple. Each week they email a question and at the end of the year they massage the responses into a bound book. A year of questions and one book will run you $99.
I can’t say for sure, but I expect that they use generative AI for a lot of the writing. That’s what I would do. If AI is good at one thing, it’s summarizing large amounts of data.
Since I didn’t know a whole lot more than they emailed questions and a created a book, I did a little poking around on what those questions might be. From my research, I was able to put together this list of 50 common questions.
- What is one of your earliest childhood memories?
- Who was your best friend growing up?
- What games or activities did you love as a child?
- Did you have a favorite subject in school?
- What did your family do for fun when you were young?
- What was your childhood home like?
- Did you have a favorite toy or book?
- What’s a childhood tradition you still remember fondly?
- What do you remember most about your parents or grandparents?
- What’s a family recipe that’s been passed down?
- How did your family celebrate birthdays or holidays?
- Did your parents have any sayings or expressions you still use?
- What chores were you responsible for as a kid?
- What was dinnertime like in your house?
- Who in your family made you laugh the most?
- What was your first job?
- What music or movies defined your teenage years?
- Who was your first crush?
- What kind of student were you in high school?
- What did you want to be when you grew up?
- What were your favorite hangout spots?
- Did you ever get into trouble?
- How did you meet your spouse or partner?
- What was your wedding like?
- What relationship advice would you give younger generations?
- What’s your secret to a lasting relationship?
- How has love changed for you over time?
- What was your first “real” job?
- What career moments are you most proud of?
- Did you ever have a mentor?
- What lessons did you learn from your work life?
- How did you balance career and family?
- What surprised you most about becoming a parent?
- How did you choose your children’s names?
- What family traditions did you create?
- What’s the hardest part about parenting—and the most rewarding?
- What do you hope your children remember about their childhood?
- What does happiness mean to you?
- What’s the best advice you’ve ever received?
- What are you most grateful for today?
- How have you changed over the years?
- What do you wish you had known sooner?
- How do you define success?
- What do you want people to remember about you?
- What do you hope future generations learn from your story?
- What moments shaped your sense of identity?
- How do you hope to be remembered?
While I will not say these are terrible questions, they seem pretty pedestrian. Asking “What does happiness mean to you” and “What was your first job” ultimately paint a fairly mundane portrait. Even their edgy questions (which are not very edgy) like “Did you ever get into trouble” leave a lot on the table. It’s almost like describing someone by looking at their Instagram account. There is a zero chance that what you come up with will be an accurate portrait. It may be colorful and shiny, but it will not be real.
A life is not important except in the impact it has on other lives. Jackie Robinson
Digging Deeper
This got me to thinking about the questions required to get down to the true essence of a human life. If I am to be remembered, I want folks to know the happy parts as well as the scars, warts, and wrong turns. I did, and still do some things really well, but I screwed up a lot and those screwups are just as important as my so-called successes. My failures define me as much as they do — especially when you consider what I did with my mistakes and shortcomings. That’s where the real growth occurred.
See the immensity of life
from the joys to the struggles
from the setbacks to the reasons we start all over again
see the flowers among the garbage
the candles that drive away the darkness
and the darkness that smothers the light
See when eyes are open
but more when eyes are closed
looking from deep within

In addition to the baseline, softball Storyworth questions, I would like to see these added:
- What are some of your biggest regrets?
- Tell about the times you were hurt by someone.
- Who are the people you hurt? What did you do to cause that hurt?
- Was there dysfunction, abuse, neglect, mental illness, addiction, or rage in your birth family? How did it carry into your adult life?
- What are your biggest fears?
- How do you deal with stress?
- What was your most difficult amend? What amends have you yet to make.
- What resentments do you still carry? Why are you unwilling to give them up?
- What changes have you been afraid to make?
- What are, or were your biggest health challenges? How did they alter your life?
- Who are the people who love you the most?
- Do, or did you have any enemies? How do you deal with them?
- What did you learn from a very difficult moment and/or person?
- What are five words you would use to describe yourself?
- What are five words you think others would use to describe you?
- What areas in your life are most in need of improvement?
- How have you disappointed people?
- How have others disappointed you?
- How do you manage your secrets?
- Are you good with money? Define good.
- Are you, or were you happy with your physical appearance?
- What makes you uncomfortable?
- Describe a moment where you felt rage?
- What did you hope to accomplish, but never got around to doing?
- Are you more of a leader or a follower?
For most people, these questions would not be easy to answer, but they are necessary to truly understand one’s life. None of us led lives that were any one thing. We were happy and we were sad. We were looked upon with love and we were abused and neglected. We were proud of our accomplishments and felt shame from our moral failures. You cannot brush your lens with only the happy emotions if you want to see a person’s true colors.
We live in a rainbow of chaos. Paul Cezanne
Tell it Loud, Tell it Proud
We all have a story to tell and revealing both our triumphs and our vulnerabilities is how we connect to one another. It’s how we turn isolation into a shared journey.
It doesn’t matter how much money you made, where you traveled to, how many minutes of fame you achieved, where you worked, who you loved, or who loved you. We are all unique, similar, interesting, simple, and complicated and our stories are worth telling. Find a way, or the ways to capture yours before it is forever lost.
And most of all, keep it real.
Thank you for reading.

Even larger than a life of strength and courage
a heart bursting with love shared and love returned
free and sometimes unexpected
This is the old growth oak
standing tall and sturdy
this is the evening star brightly shining
as kinetic as the universe and its ever expanding ways
All that bigness
all that wonder and awe
All day long

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