Author’s Note: When my wife was diagnosed with terminal cancer, I started compiling questions that our children would want to learn someday. We recorded a legacy video that I’m grateful we will have for the kids to see – most people don’t do it and wish they did.
So, weather you’re wanting to use an online legacy platform, or DIY and record your own video or just have some meaningful conversation starters, I hope this list will help you connect, reflect and remember your loved ones.
This process doesn’t have to be sad, and there’s no reason to wait until someone has been diagnosed with a terminal illness. I hope this list can be helpful for more people.
Early Life and Family Background
- What is your earliest memory?
- What were your favorite activities as a child?
- Tell me about your fondest childhood memory.
- Who had the most positive influence on you as a child?
- What stories have you been told about yourself as a baby?
- What were your parents like when you were a child?
- Do you have any particularly vivid memories of your grandparents?
- What did you learn from your parents?
- Who inspires you, and how?
Achievements, Experiences, and Choices
- What do you consider one of your greatest achievements in life?
- Tell me about one of the best days you can remember.
- What is one of your favorite trips that you’ve taken? What made it great?
- What is one of the bravest things you’ve ever done, and what was the outcome?
- Have you ever given or been the recipient of a random act of kindness?
- What inventions have had the biggest impact on your day-to-day life?
- Have you ever won anything? What was it?
- What was your first job, first boss like, and your favorite job?
- Did you consider any other careers? How did you choose?
- What was your best boss like?
Review our guide with dozens of recommendations for online legacy and archiving platforms and DIY projects to help you preserve your parent’s memories.
Personal Reflections and Values
- What qualities do you most value in your friends?
- What things matter most to you in life?
- What advice would you give your young family members?
- What have you changed your mind about over the years?
- What do you think is the meaning of life?
- What gives you peace of mind?
- What things do you think you cannot live without?
- What is one of the most selfless things you have done in life?
- Wishes, Hopes, and Fears
- What would you consider your motto?
- What are your hopes for the world?
- What do you hope for different people in your family?
- What are your fears for the future or personal fears?
- If you could thank anyone, who would it be and why?
- If you could have any talents, what would they be?
Personal Favorites and Leisure
- Favorite memory, food, color, ice cream flavor, snack, dessert, book, movie, drink, cuisine, athlete, television program.
- What is your most important possession and why?
- What are some of your special talents that people might not know about?
- What was your first car? Your favorite car?
- What about being a child do you miss the most?
- Would you prefer to have an adventure, or read about one?
Later Life and Legacy
- What advice did your parents regularly give you?
- Do you have any keepsakes or heirlooms from your parents?
- How do you want to be remembered by your family and friends?
- What stories or values do you wish to pass down to future generations?
- What has been your secret to a happy and fulfilling life?
- How has your life turned out differently than you imagined it would?
- What have been some of your life’s greatest surprises?
Thoughtful Life Reflections
- At what times in your life were you the happiest, and why?
- Do you have any big regrets in life? What advice would you give to others so they can avoid the same regrets?
- Which fads did you embrace while growing up?
- Who is the wisest person you’ve known? What have you learned from them?
- How has the country changed during your lifetime?
- What is one of the strangest things that has ever happened to you?
- What is your idea of perfect happiness?
- Are you more like your father or your mother? In what ways?
- Have you pulled any great pranks?
- What is your favorite joke?
- Who had the most positive influence on you as an adult?
- Has anyone ever rescued you, figuratively or literally?
- Who would you like to have lunch with (historical/current)?
- What is the farthest you have ever traveled?
- How has your life turned out differently than you imagined it would?
- What was your first big trip?
- Who has been your biggest inspiration?
Why It's Important to Ask These Questions Before It's Too Late
Asking your parents these questions may seem uncomfortable or even morbid at first, but the insights and memories you gain from these conversations will be invaluable. Not only will you gain a deeper understanding of your family history, but you will also strengthen your relationship with your parents by showing them that their stories and experiences truly matter to you. Don’t wait until it’s too late – start these conversations now and create a lasting legacy for your family.
As a courtesy, we’ve put these questions into a google doc that you are welcome to copy, customize and use for your DIY legacy project.
