There are abundant resources online and in libraries for family history questions. You know the kind I mean: checklists of all the possible questions you can ask the grandparents, military veterans, immigrants, distant cousins. One of my recent favorites is the #52Stories project from Family Search, which provides 52 prompts for capturing one brief story about your life every week, hopefully motivating you to begin shaping your family’s intergenerational narrative.
But if you’re in the market for more thought-provoking conversation starters—deeper questions that you can ask relatives or yourself on your journey of documenting your life stories—then we’ve got three unexpected resources for you. The questions included in these recommendations are often provocative, occasionally off the wall, and always open-ended to encourage a full, meaningful answer using the subject’s own experience and feelings.
The Best Questions Yield the Best Answers
If you select questions thoughtfully, you’re sure to get revealing answers. Whether you choose to use those answers to inform writing your own memoir, as episodic stories in a personal history book, or merely as a means of self-development or family bonding, you’re guaranteed to learn something new about yourself in the process!
1 - Gravitas: The Little Box of Big Questions
Gravitas is a powerhouse of thought-provoking questions. This parlor game of sorts engages “players” in conversation with questions that call for reflection yet can be dealt with in a thoughtful or a more lighthearted manner. While the goal of the game is ostensibly to declare a philosopher king of the occasion, the real value in this “Little Box of Big Questions” is to get everyone offering thoughts on life’s big questions as a way of discovering who we really are and how we have lived.
Here is a sampling of the prompts (there are 429 questions in the box), designed to spark meaningful conversation and profound insights.
- What takes your breath away?
- What is your gold standard for a good friend?
- How do you ‘carpe diem’?
- Describe the gap between life as you imagined it and life as it is.
- How do you practice kindness?
- When they say you have to work hard at love, what do they mean?
And a few less profound options to keep the banter flowing—questions that could as easily invite surprising insights and wisdom as they could a punchline:
- If we are what we eat, who are you?
- When does the fun stop?
- What is the best thing you have ever found?
- They say that Seinfeld is a TV series about nothing. Any ideas for an episode?
- Who would you like to eavesdrop on?
2 - Know Yourself: Cards for Self-Exploration
This small box of 60 prompt cards is less about conversation with others, like the Gravitas questions above, but rather about conversation with oneself. They delve straight into big-picture, deep ideas and often read like prototypical “head shrink” questions—but when approached with an open mind and a truly self-aware lens, these prompts can undoubtedly help us understand ourselves better.
Some of the questions in the Know Yourself box are clearly intended for private introspection, such as “What things would deeply alarm your loved ones if they knew them about you?” and “What are you currently lying to certain people around you about?”
Many of them, though, are wonderful prescriptions for prolonged thought or writing assignments that will yield worthwhile insights:
- When do you cry or want to cry (as an adult)?
- What did you learn about relationships from your parents?
- List everything you are worried about, from the very large to the very small.
And some, well, simply invite interesting answers:
- What are you trying to say through your clothes?
- If a really kind person wanted to praise me, they’d say… If a really tough person assessed me, they’d say…
- Name three works of art (music, literature, and visual art/architecture) that mean a lot to you.
I recommend consulting these questions if you are an aspiring memoirist or avid journaler who wants to be challenged to explore who you are, or just a curious soul craving a gentle nudge towards deeper self-reflection.
The cards are produced by The School of Life, who bills itself as “a global organization dedicated to developing emotional intelligence [applying] psychology, philosophy, and culture to everyday life.” Visit their site for a treasure trove of resources to enlighten and entertain. And if you decide to check out their Confessions Game—“a series of questions around career, sex, money, relationships, family, gently inviting everyone to share important bits of themselves in an intimate and playful atmosphere”—please let me know what you think, particularly if the questions might be helpful for memory-keepers and life story writers, too!
3 - If… (Questions for the Game of Life)
Writing one’s life stories requires not just looking towards the past, but also looking towards the future. It is our hopes and dreams and the life we imagine for ourselves that define us as much as the paths we have already taken—and preserving those thoughts for future generations is a worthwhile endeavor.
“Fantasies are what inspire us all; to work, marry, raise families, create, improve our world…. We imagine in order to learn, to understand, to strive, to attempt, to predict, to avoid, to correct, to describe, to solve,” write the authors of If: (Questions for the Game of Life) (Villard 1995). As you may have guessed, every question in this book begins with the word “if.”
Perhaps some of these questions lean towards the cliché (there are plenty of the if-you-could-dine-with-anyone-from-history variety), but that in no way diminishes from their purpose: to spark your imagination, and to provide glimpses into your personality and life. It is their accessibility, and their ability to make you step outside your everyday worries, that make them worthwhile.
These are a few of the questions that, in my opinion, go beyond the expected and provide impetus for life-story writing or conversation geared toward meaningful reminiscence:
- If your plane were about to crash and you had time to write one quick note, to whom would you write, and what would you say?
- If you could, in retrospect, change one thing about your childhood, what would it be?
- If you could discover that something you thought was true was actually false, what would you wish it to be?
- If you could gain total memory of one year of your life so far, which year would you pick?
If is a book that can be tucked away in your car’s glove compartment to make long road trips bearable, or it is a book that can be stashed in your bedside stand for instant journaling inspiration.
And now, some questions for YOU.
- What is the one question that you find always elicits interesting stories?
- If you could have asked one question of a deceased family member, what would you have asked, and to whom?
- What other sources of interesting questions are in your repertoire? Books, websites, podcasts?
Please share your thoughts in the comments below—I’d love to hear from you!
Who Will Tell Your Life Story? It can be daunting to think of writing (or even telling!) your life story. So don’t. Start saving your stories, one at a time.