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“I wish I had asked my mom that” and other heartbreaking regrets YOU can avoid

Ask your parents to share stories from their life—not only will you have the security in knowing their legacy is preserved (no regrets of unasked questions!), but you’ll undoubtedly gain some laughs and lessons along the way.

If there’s one thing I’ve learned over and over again in this business of memory keeping, it’s that we all take our loved ones for granted—and we think that tomorrow or the next day we’ll be able to have that meaningful conversation. I struggle with finding a way to convey to everyone just how important it is to both

  • ask our parents about their lives

  • and tell them how we feel

—and to do so now.

Unfortunately, for many people, it’s only stories of regret that sink in:

I could tell you the story of my friend who came out as gay to his mom as she lay in her hospice bed, unresponsive. He likes to believe she heard him.

I could tell you the story of my client who had a million ideas why her mother was so emotionally closed off, but who never asked her mother to share her experiences. She is haunted by her many questions…and lack of answers.

I could tell you the story of an almost-client who booked me to interview her grandfather, who was a Holocaust survivor, only to have him die two days before our scheduled interview. We shifted to creating a tribute book in his honor, but how much more special would having his own stories have been?!

Often I simply share this powerful quote from William Zinsser that says so much with so few words:

“One of the saddest sentences I know is, ‘I wish I had asked my mother about that.’”

Have you asked your parents or grandparents about their lives? If that seems like something you just don’t have time for, please think again.

3 ways to ask your parents for their stories—before it’s too late

Not sure how to capture your parents’ stories? Here are three foolproof ways to invite, hear, and preserve your parents’ stories. Whichever you choose, I implore you: Get started now.



  1. Record an interview with your mom or dad.

  2. Ask your parents to write about their memories.

  3. Hire a pro to help your parents record their stories.


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1 - Record an interview with your mom or dad.

No need to overthink this—just find a way to sit intentionally with your parents for the express purpose of listening to their stories. Use an audio or video recorder to capture the conversation. You can always decide what to do with it later. Choose questions from this free guide, or make them up as you go along.

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2 - Ask your parents to write about their memories.

They don’t have to think of themselves as writers to undertake a project such as this, but they do need to be committed to writing regularly. So, provide them some friendly accountability: Ask if they’ll call you once a week to read their stories to you (and your siblings, if you have any—a fun excuse for a Zoom get-together!); or, undertake an email correspondence with your parents where you ask the questions and they reply with their stories.

I recommend they spend an hour or so brainstorming a list of memories, then use the items on that list as prompts for their life story writing; or consider signing up for a class with weekly memory prompts to get them going.

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3 - Hire a pro to help your parents record their stories.

Whether your parents don’t have the stick-with-it-ness to keep writing, or you’re too busy or otherwise unable to interview them, or you simply want the best experience possible, consider partnering with a personal historian such as myself to record your parents’ stories and preserve them in an heirloom book. I’d be happy to chat with you about the ways to bring your project to life.

A surprising benefit of going this route: Some people feel more comfortable telling their stories to an open-hearted stranger as opposed to a family member—it could be because they know they have a captive audience who hasn’t heard their stories before, or because they may fear familial judgment for certain experiences or decisions in their past—but whatever the reason, the stories often flow more smoothly and fully when told to a professional interviewer.

This approach also allows you to let your parents know how much your stories mean to you while taking the pressure off you to guide the project through to completion.




Whether you interview your parents or ask them to journal about their life, let them know, in no uncertain terms, that their stories hold value for you. Convey just how special this undertaking is to you and not only will you get their stories, you’ll inevitably grow closer in the process.

Modern Heirloom Books offers plenty of free family history resources to help you interview your parents and capture their stories for posterity, including this guide, “56 Essential Family History Questions to Ask Your Parents Before It’s Too Late.” Click the button below to access it right now!