Reimagine Goodbye Back to Work With Me

A legacy project

Tell Love Stories

Make time to thoughtfully share stories—and record them, if desired—so you can revisit them for many years to come and share them with future generations.

Create a quiet space and select just a few of these at a time—record audio or video—and go slow with these—take your time. Linger in the details and the feelings. Pause to imagine your loved one at the time. Dwell in it with them.

Taken in small portions of time, these questions can create a beautiful library of stories and a meaningful walk down memory lane.

Childhood & Early Years

  1. Tell us about your family when you were young. Where did you live? Did you have siblings? Was extended family nearby?
  2. What were your parents like? If you had to describe each of them in three words, which words would you choose?
  3. Tell us about your siblings—or people who were close enough that they felt like siblings.
  4. What was your favourite holiday as a child? What traditions, people, places, clothes, sounds, or feelings do you remember?
  5. Did your family have special hobbies or pastimes? What did you enjoy most? What could you have done without?
  6. Who were you closest to in your family? How might they have described you at age five, ten, or as a teenager?
  7. Did you live in one home for most of your childhood or move around? Was there a favourite place or chapter?
  8. Did you have a pet or best friend who played a special role in your life?
  9. Can you remember a favourite vacation that made a lasting impression?
  10. What music, meals, books, or movies do you recall from that time?
  11. How would you describe what it felt like to be a child in that time and place?

Teenage Years & Twenties

  1. Do you remember becoming a teenager? Was it celebrated or treated like a regular birthday?
  2. What was the most mischief you got into? What did you do that scared you—and you didn’t get caught?
  3. How was being a teenager then different from what young people experience today?
  4. What was dating and finding a partner like in that era of your life?
  5. Do you remember your first dance? How did it feel, and what music from that time stays with you?
  6. Do you remember the first time you saw your husband, wife, or partner? What did you think?
  7. Tell us about your engagement and wedding. What makes you laugh? What brings a tear to your eye?
  8. How did you feel during this chapter about one day becoming a parent?

Parenthood & Grandparenting

  1. How did you share the news that you were going to become parents?
  2. What were some of the dreams and worries of that time?
  3. How did becoming a parent change you and your partner?
  4. What really surprised you about parenthood?
  5. What do you wish you had known then? What would you write in a letter to your younger self as a new parent?
  6. As the children grew and you learned to let go a little, how did that feel? What did you learn?
  7. Looking back, what is one thing you might have done differently?
  8. What are your favourite memories of family trips or traditions?
  9. What are your favourite stories of times your children made you laugh?
  10. What individual blessings has each child brought into your life?

Work, Purpose & Success

  1. What did you want to be when you were growing up? How close was the reality?
  2. Did you dream of the level of success you’ve had? What do you think was the secret to it?
  3. What is one thing you might have done differently in your working life?
  4. What was a huge win that felt especially good?
  5. Who influenced you most in business or work? Was there anyone who challenged you?
  6. What is your definition of success? Is it the same today as it once was?

Wisdom & Wonder

  • When did you last lose track of time in the best way? What makes you feel most alive?
  • What have you loved most about being alive?
  • When, if ever, is being right better than being kind?
  • When did you last say yes even though you wanted to say no?
  • What is your “I wish” statement?
  • How would you like this story to end?
  • What is one thing you hope your grandchildren always know or remember about you?
  • What is the nicest thing a friend has ever done for you?
  • Who has influenced you, taught you, or inspired your admiration most?
  • What did you believe for much of your life that you no longer believe in quite the same way?
  • What is the best compliment you ever received?
  • Have you ever had a supernatural experience? What happened?
  • When do you wish you had been bolder?
  • If you could ask your grandparents one or two questions today, what would you ask?
  • What do you hope others say about you when you leave the room—and when you leave the planet?

Next Chapters & End of Life

  • As you move closer to the end of life, what matters most now? Who do you want to spend more time with?
  • Are there conversations that feel important to have?
  • Is anything left unsaid or undone that you would like to address?
  • Are there burdens, regrets, or resentments you would like to release—for yourself or others?
  • What brings comfort, peace, or joy to your days right now?
  • Which parts of your life story do you most want remembered and passed down?
  • What was your earliest experience of death? What meaning did you give it, and how have your thoughts changed?
  • Do you think about your last days? What are your hopes for that time?
  • Who do you hope will be nearby? What music, scents, sights, and sounds would bring comfort?
  • If you could choose them, what would you want your last words to be?
  • What do you most want the people you love to know?

Keep these questions close

Download a beautifully formatted copy to keep, or print the questions to bring to your next conversation.

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