How to Collect, Organize, and Preserve Family Memories and History (Part 1) — The Questions

Posted on: October 14th, 2024 by Julie Bestry | 18 Comments

It’s hard to believe that we’re in the final stretch of the year; next month will be Thanksgiving, with the various winter holidays coming up right behind. It may be a joyous time spent with family or one marked by an empty seat at the table, a time of sharing new and old stories and, sometimes, grieving the questions un-asked and stories never told.

Over the next two posts, we’re going to look at ways of gathering and preserving your family stories so that future generations will have no regrets about what they’ve missed.

PAPER DOLL’S FAMILY HISTORY (AND FICTION)

Paper Doll is naturally curious. I have annoyed Paper Mommy (both as a child and as an adult) by insistently begging for tales. “Tell me a story about your grandparents that I haven’t already heard!” or “Tell me about when you were in school!” I urge my mother, to her frustration. She retorts, “I tell you things when I remember them. I can’t call up stories at the drop of a hat!”

As someone who is practically built out of words and memories, I can’t fathom it. Ask me about my first day of kindergarten, or my first date (an extremely embarrassing skating story everyone somehow remembers clearly) or the day I bought my car, and I can recite it as if it happened thirty minutes ago.

My family finds this annoying.

I find the lack of stories annoying. I want a complete biography, with footnotes, of my mother’s life — every conversation and experience I missed from the day she was born until I was a toddler, I want filled in. And the ones I know by heart, I still want to hear her tell them over and over again, complete with accents and narrative flourishes. 

My favorites? The time in her nursery school education class where the miniature turtle went missing after the toddlers left, but (after a length search) was found in the back of a teeny toy dump truck. The time when my great-grandmother, who ran terrified of a dog chasing her from the streetcar and hid on the floor of the closet during thunderstorms, nonetheless ascended a ladder and climbed in a window when she was locked out of the house. (That’s my mother’s Bubbe on the far right, below.)


I know how my mother’s father came to America. He, his father, and his brother set out from home in Poland so his brother could take a boat to America, but (as you likely learned in Social Studies), people with diseases of the eye could not be admitted. (It’s an imprecise analogy, but imagine your nine-year-old’s pinkeye caused your family to be turned away at Disney World!) My great-uncle’s suitcase was thrust into my grandfather’s hands, and the teenager set off for America.

I’ve heard a few stories about my Poppy, some surely apocryphal. (Only many decades later did we start to doubt the tale of his job unloading cargo on the docks: a burlap bag of chocolate burs open, upon which he and his fellow worker filled their pockets with chocolate and ran away. Um, did chocolate ever come wrapped in nothing but burlap?)

Other stories were also questionable, such as when he told of a man running a food cart being asked for a hot dog. The cart only served fish, so the cart owner gave the man a fish sandwich, and the man was heard saying it was the best-tasting hot dog he’d ever had! (Years later, my grandmother, feeding my toddler uncle, urged him to eat the yummy hot dog he’d been requesting. It was a soft-boiled egg. Perhaps my Poppy’s story was the catalyst?)

Still,  there are verifiable stories. My grandfather bought part ownership of a decommissioned battleship as scrap metal, and later owned an apartment complex he named after my sister. A friend researching genealogy found a Depression-era news article about him being robbed of of hundreds of dollars cash (because he didn’t believe in banks) but was not destitute because he’d also hidden money in his socks.

And once, my mother exited a downtown summer camp reunion luncheon to find her father — a Jewish man from Poland — at the head of Buffalo’s St. Patrick’s Day parade! 

And yet, we know nothing of his life before he came to America except his mother was tall and that his father was, circa 1910, the captain of the town’s fire brigade. When my maternal grandparents were visiting in the mid-1970s, my grandfather slipped on the Buffalo ice and went to the hospital. Fed up with the pesky questions demanded by the hospital, my grandmother snapped when the nurse wanted my grandfather’s mother’s name, and made up a random name that sounded shtetl-appropriate.

Paper Doll with Poppy, circa 1968 or 1969 (The booklet we’re “reading” says it “will tell you how you can become a Computer Programmer.”)

As I described in The Great Mesozoic Law Office Purge of 2015: A Professional Organizer’s Family Tale, it was only when I closed down my father’s law office that I connected with his cousin and learned that my paternal grandfather, whom I always imagined to have grown up in vague immigrant-era poverty, was decidedly more Upstairs than Downstairs.

Indeed, until recently I knew nothing of my father’s father’s family, and have been fascinated by what my genealogist friend’s have found. I didn’t even know my great-grandfather’s name before reading this obituary, let alone that he owned a hardware and tinsmithing store. (When was the last time you heard about “tinsmithing?”)

I only knew of two of my grandfather’s sisters; two others plus a brother were surprises to me. Nor had I learned that my grandfather’s brother became a Broadway performer and impresario! Why was I never told these stories? My father was more interested in his future than his family’s past, I suppose. 

Speaking of my father, he was a clotheshorse and chronically disorganized. So, I was amused to find this post, referencing my Great Uncle Mike “Harry” Bestry:

Damon Runyon wrote in Short Takes, for example, that Harry Bestry owns or owned “3,000 Charvet neckties, which is more than Charvet has now, 75 suits of clothes by an expensive tailor, 75 pairs of shoes, each pair made to order and nicely treed, and hats and shirts and overcoats and sweaters in similar profusion.” He added that a friend of Bestry once reported one could barely get into the man’s apartment “because of the amount of wearing apparel stashed away on the premises.”

There’s something odd about knowing that the person who created Guys & Dolls wrote about my relative. Odder still that this could absolutely have been a description of my own father.

When I was home in June, helping downsize and declutter the family basement, I found a scrapbook my father’s first wife made of their trip to New England in 1951 and a few after that. His bride’s careful penmanship next to each piece of memorabilia detailed not only their trip, but the era. On the same page, she extolled the virtues of a restaurant meal but also noted the antisemitism of the hotelier announcing that the hotel — at which my father and she (both Jewish) had been welcomed — was restricted. No Jews allowed. (They departed before nightfall.)

[If you’re unfamiliar with this era in American history, you might want to see the Gregory Peck film based on the Laura Z. Hobson novel, Gentleman’s Agreement, in which Peck plays a journalist who goes undercover as a Jewish man to explore post-War antisemitism.]

As I reviewed the scrapbook, I absorbed the details of each crumbling page which had been lovingly assembled over seventy years ago by a woman who died perhaps sixty years ago. I was fascinated by the notations of someone to whom I had only a tangential relationship, narrating weeks in the life of someone with whom I shared half my DNA.

Of course, family history comes with world history. I was fascinated by the prices on the menus.

At Keeler’s State Street in Albany (established 1864), a whole baby pheasant with sides of lima beans and wild rice could be had for $3.50, with desserts from 30 to 60 cents. (Eat up quickly! Parking was twenty-five cents an hour!)

Meanwhile, New Orleans’ Restaurant Antoine (founded 1840, and which still exists) cost them a prettier penny. It was a multi-page menu, but my focus was on the eye-popping price of $7 for chateaubriande! Splurge further: $1.25 for a Crêpe Suzette for dessert.

WHY CAPTURE YOUR FAMILY HISTORY?

This is all to say that if you aren’t inclined to ask, and if your relatives aren’t inclined to tell, it can be difficult to create any sense of family legacy, either for yourself for for generations that come after.

In her excellent book, What’s a Photo Without the Story?: How to Create Your Family Legacy, my friend and colleague Hazel Thornton details why you might want to gather your stories and those of your family and your ancestors. At the start of the book, she explains that doing so will:

  • Give depth and meaning to your photos.
  • Make history come alive!
  • Preserve family legends  (rumored or proven).
  • Give children a sense of belonging and help them feel more secure.
  • Make us feel connected to our families , and to the world around us.
  • Help us better understand our families, and ourselves.
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For more on specialists like Hazel, take a peek at Paper Doll Interviews the Genealogy Organizers

HOW TO SET THE STAGE FOR ASKING FAMILY HISTORY QUESTIONS

In some families, older relatives may feel frustrated and put on the spot if they feel they’re being interviewed, while others might enjoy the spotlight.

Only you know what your relatives would prefer, but it may help warm up the interest (and the memory) to start with questions that develop more naturally, rather than seeming as though they’re being interrogated.

Share an activity together

Whether you are setting the table for Thanksgiving or the High Holidays, there’s a ritual to preparing food and setting the stage for a family meal. That’s a great opportunity to use the ebb and flow of the activity to tease out the stories of your mother’s or grandmother’s life, whether it was during the Great Depression or the 1980s.

Ask: Who was at your holiday table? Which relatives did the cooking? Did everyone follow traditional gender roles? What foods did you always have? What was the rest of the family doing while the meal was being prepared? Was it a formal or informal experience? Did everyone get dressed up? Was there a grown-up table and a kid’s table?

If you’re attending (or even just watching) a ball game, use those 7th inning stretches or longer commercial breaks to warm up the conversation. On a family vacation? Ask about the trips they might have taken in their youth. 

You may know (or think you know) bits and pieces of a family story, so start there and be open to being corrected.

Go on a “road trip” whether by car or foot

Whether you’re going over the river and through the woods by car to a relative’s house or just taking an amble through the neighborhood to enjoy the changing of the leaves (and walk off a tryptophan-heavy turkey dinner), being in motion has a few advantages when you’re trying to prompt memories.

First, sometimes it’s easier for people to recall and share memories when they don’t need to make eye contact. As the two of you face forward, either while strolling or driving along, you can ask direct questions without them feeling like they are the center of awkward attention. (Of course, some relatives like to be center stage to spin a yarn; experiment until you figure out what each one prefers.) 

Additionally, when you’re walking, the motion keeps the blood flowing, which may keep the conversation flowing as well!

Driving around the “old neighborhood,” whether it was a decade or half a century ago, can prompt stories. On various trips home, Paper Mommy and I have driven to various of the homes she lived when she was a teen or young bride, and it always prompts interesting (and funny) stories.

Share your own stories and seek comparisons

It may help to bring up a story of your own, or one you’ve heard. If someone you know recently got engaged, for example, you could talk about that experience and ask how it differed for them. 

What was the proposal like? How did the parents on both sides feel? Who was in the wedding party? Was it rushed because someone was headed off to war, or planned in detail? Were there bridezillas in the family history?

Similarly, talking to your relatives about school, about finding their first jobs or setting up their first homes, about having children, about long separations or special occasions — all of these stories may be more easily prompted when you tell your own stories, first. Sometimes, people feel like they have no tales to tell until they can compare and contrast with another’s experiences.

Use photos or physical props, perhaps as part of the downsizing process

Eighty percent of our family photos were taken by my father between the mid-1960s and about 1980; there’s not a lot from prior to then. Later, I started taking pictures with my mother’s 1960’s era Brownie Instamatic (the kind with the square flash cubes you snapped into the top). I thought I’d seen them all, but on my most recent trip home, I came across a stash of photos I’d never seen before.

A little worse for wear, my mother’s 8th grade graduation photo from 1949 was an amazing time capsule. Starting in the front row and going left to right, and then moving back row-by-row, I asked my mom about the people in her class. Understandably, many had been forgotten, but names and anecdotes started to arise, and I even knew a few of the people in the photo but only as adults, many years later.

Use the opportunity of preserving/scanning old photos to start asking questions about who the people were, and how they fit into the family stories.

Similarly, as you help relatives downsize or streamline their homes, ask about the history of pieces of furniture, decor, heirlooms, and memorabilia you come across

WHAT TO ASK YOUR PARENTS OR GRANDPARENTS

You’ll have your own ideas of what’s important to know and ask, but if you’re stuck, use these prompts to get you started.

Ancestors and Relatives

You might start by asking about the generations that came before. They may assume you know stories about relatives you vaguely, barely know (or don’t know at all).

  • How did their parents (or grandparents on either side) meet?
  • Where did their families live when they were born? Did other family members live with them?
  • How did they come to live where they did — either how did they come to North America, or to the various cities where they’ve lived and settled down?
  • What did their parents do for a living? — My paternal grandfather was in a business partnership with his brother-in-law; they sold tailors’ notions. My maternal great-grandfather was a baker, and the part of his obituary that notes that he “specialized in pumpernickel and bagel” always makes me smile.

  • How many children did they have? (If their stories predate the mid-20th century, you might ask how many children survived. My grandmother was one of six daughters, besting even Tevye’s five in Fiddler on the Roof, but sadly one died in the early 1930s, leaving a bereft fiancé.) 
  • Did they have any fun nicknames? (Two of my great-aunts had “boyish” nicknames; Miriam was Mickey and Laura was Larry.)
  • What were each of them known for? Did they have any interesting skills or talents?
  • What stories do they have about extended family members? (My mother’s first cousin, Sandy Konikoff — and yes, I’ve forgotten again if that makes him my first cousin once removed or my second cousin — is a famous drummer. He was a session drummer on albums like Joe Cocker’s Mad Dogs and Englishmen and played gigs with Bob Dylan in the mid-1960s. That’s him, below, on the far right.) 

Childhoods

  • Where did they go to school? Were they good at school? 
  • Do they have a favorite teacher? One(s) they despised? (Paper Mommy had a teacher who had a mean nickname for my mom. It’s probably been 75 years, but even now we don’t think kindly of that woman; meanwhile, I am still intrigued that my mother took Industrial Arts in the 1950s (from a teacher missing a few fingers).)
  • How did they get to school?
  • Did they each lunch at school or go home at lunchtime? (Lunch was not served at my mother’s grammar school, and imagining her bundling up and shlepping home in the snow for lunch prepared by her Bubbe — while her mom was Rosie the Riveter at the airplane factory — and then trudging back to school again fascinates me. It was a far cry from my mom’s daily trips to ferry me to and from school and the orthodontist and everywhere else in her Chevy station wagon.)
  • Did they wear uniforms?
  • Did they have extracurricular activities?
  • Did they have to work after school?
  • Who were their best friends? What did they do together?
  • Were they good kids? Did they get in trouble?
  • Did their family take vacations? Where? What’s their most memorable family vacation?
  • What was the financial situation like? Did they have any awareness of how much money their family had?
  • Did they get an allowance? How much? What did they spend it on?
  • Did you have to do chores?
  • Did they have their own bedroom or share it? What was that experience like?
  • What big historical events do they recall living through? (You can always fall back on “What do you recall about World War II?” Where were they when JFK or MLK or RFK was killed? Future generations will ask about 9/11 or January 6th.)
  • How far did they go in school?
  • If they went to college, ask them to tell you all about their college experiences. Ask about where they lived and with whom, what classes they took (and why).

Romances

  • Were they allowed to date? Did their parents set any particular rules about dating?
  • Who was their first crush? First date? First kiss?
  • Who broke their heart? (Paper Mommy is blasé about how many proposals she got, but tells lively tales about the bad ex-boyfriends. Most intriguing? The ex who sent her a dozen long-stemmed roses with a card that read, “May you prick your fingers on every thorn.” Some guys just can’t handle rejection!)
  • To whom did they propose or from whom did they receive proposals?
  • Do they have any romantic regrets? Who was the one who got away?
  • How did they know they’d found the right person (if they did)?
  • What advice do they have based on their experiences?
  • How did they meet your other parent (grandparent)

Careers and Adulthoods

  • What did they envision wanting to be when they grew up? Did they end up doing that?
  • What was their first real job? Do they remember what they got paid?
  • Were they ever in the military? Were they drafted?
  • What were their dreams? Which did they achieve? What do they still want to do?
  • What did they imagine the world would be like when they were older?

Whatever questions you ask, be prepared for the questions to meander into unanticipated territory.

LOOK BEYOND BLOOD RELATIVES

About a decade ago, while visiting my mom, I had a sudden urge to know more about how our dear family friend Jennie, much like an aunt to me, had met and married her late husband. Dave was a delightful teddy bear of a guy — similarly ever-present when I was little — and I asked if my mother and I could come over and have her tell me the story.

Jennie was surprised, but happy to share her lovely WWII-era story of romance. A soldier, visiting his girl and her friends, brought along his fellow GIs. Fresh from the shower, her hair was in curlers when Dave first met Jennie, and he seemed to pay little attention. Indeed, upon their meeting the next day, he didn’t even recognize her…but he fell in love.

(I hadn’t yet mastered taking a photo of a photo without getting a blob of flash. Nonetheless, don’t Dave and Jennie look like a promotional photo from a post-War film?)

Jennie passed away just a few years ago at the age of 97. While she wasn’t family by blood, she was my Tooth Fairy (Paper Mommy couldn’t bear those wiggly teeth) and even just a few years ago was the source of some fabulous phone conversations about Grey’s Anatomy. (She agreed that Alex would never have left Jo.) 

Sometimes, your family legacy extends beyond the genealogy chart.


Obviously these are not one-and-done conversations, but hopefully the foregoing has given you some great ideas for how you might start your journey into collecting memories and family history.

Asking questions is just the first step. Securing the answers for future generations may require a different type of effort. Certainly, you can record these conversations as an audio note or video on your phone, or you may choose to take advantage of a wide variety of apps and services designed for the purpose.

Next time, we’ll look at technology, from simple recording to AI-assisted efforts, for preserving your family history.

18 Responses

  1. All holidays for my family, Thanksgiving, Christmas, and Easter were with my mother’s family. It was (still is) a huge family. There were many family members in New York City, where I grew up. I have endless stories of my grandmother and her siblings – stories that I heard recounted time and again.

    My siblings and I only gather rarely. Geography- living far apart – is one of the reasons. The other is that we’re all busy and don’t take as much time for holidays as we once did. My older son loves the stories. So I share the ones that occur to me.
    Thank you for all the questions. I’ll share the questions with my sons and encourage conversations!

    • Julie Bestry says:

      I hope you get some great tales!

      My family is small — and my father had no siblings and never shared stories, and his parents were very quiet people. It took a long time to find some stories and even to know what might be there. I’m hoping this post will help people learn more about their family’s histories while they still can.

      Thanks for reading!

  2. Seana Turner says:

    How fun to read all of this history of yours. You have made some fascinating discoveries!

    I relate to your discussion of being sensitive about asking people for family stories. I remember a time over dinner asking my parents about when they met and their early romance. The details seemed pretty brief, and my father seemed resistant to discuss it. This made me realize that you need to tread lightly. You never know when a family member may have a part of their story that they wish to forget, or at least keep from perpetuating.

    On a more positive side, I remember my daughter was given an assignment as a child to interview a family member. She interviewed my mother, and it was all recorded on an audio cassette. Reading this reminds me that I want to get that transferred to digital format to preserve it. It really is a treasure!

    • Cathy Borg says:

      This blog post is a great reminder to cherish our family stories. Your questions are a helpful start. I’m inspired to start asking my own family more questions. Thank you!

    • Julie Bestry says:

      I’ve noticed that when I engage my clients and ask questions related to things we’re downsizing, they’re eager to talk. Sometimes their adult children express surprise. It can be that nobody has shown interest, or that it takes years or decades to feel ready to open up. It definitely takes light, gentle “treading” to get some stories out.

      What a great project your daughter got to do. (I remember when big, bulky cassette recorders were just coming on the market!) Definitely digitize that interview; tape breaks down!

      Thanks for reading!

  3. Julie- What a rich, vibrant collection of family stories, pieces of history, and conversation starters! I also love the images you shared of old menus, newspaper clippings, and photos.

    It’s fascinating how you’ve been a curious question-asker since you were little. I love that about you! And because of your inquisitiveness, you’ve collected many treasures that are now captured for your present and the future.

    At this point, most of the elders in my family are gone. My brother and I had a conversation yesterday about something he wished he asked my mom for more details about. There was a story she used to tell us frequently about one of her college professors. She’s no longer here to ask, but my brother will try to find out through other sources. We’ll see.

    It speaks to your point. Interview and have those conversations while your loved ones are still here.

    • Julie Bestry says:

      Awww, thanks, Linda. I’m the end of the line, family-wise, so I won’t have any kids or grandkids with whom to share these stories. So, the next best thing is to share them with readers in service to a larger focus on organizing family legacies.

      I hope your brother is able to flesh out the story about the professor; when he does, please share it, as now I’m curious, too!

      And yes, we mustn’t wait. And next week’s post will give us more pointers on how to put all of these prompts into action!

      Thank you for reading and for your supportive comments!

  4. Brian O'Hara says:

    Once again a fun and full description of what to do, why to do it, and suggestions for how to make it happen! A most enjoyable and practical piece. I will work on some of the questions at the next extended family gathering.

  5. Great post. I also love hearing stories, which my mom was good at producing, but my dad was not, so I don’t know a lot about his upbringing.
    Years ago I gathered photos of both sides of my family and my husband’s family. I created a family wall in my dining room where I hung them. At the center of the wall is a family tree and I made sure that every person in the photos is noted on the back. I don’t know if my kids will want the photos, but I have enjoyed having them.

    • Julie Bestry says:

      What a lovely way of capturing your family history visually! While it’s possible that not all of your children will be attached to this information when they are older, I bet at least one will be, and will be eager to share it with future generations. May I suggest that you take one master photo of the entire layout so that if there are any questions in the future regarding how it was laid out, they’ll be able to rely on that?

      Thanks for reading!

  6. This is SO up my alley (and I also love Hazel’s book). Sadly, there aren’t many people left who can share stories or answer questions any more. I wish I’d been more interested when I had the chance. 🙁

    On the other hand, I did a DNA test this year and have connected with a few relatives who know stuff that I don’t (and vice versa) so there’s that. 🙂

    • Julie Bestry says:

      I think it can be a vicious cycle. Not everyone wants to tell stories (think of how the Greatest Generation folks often didn’t/doesn’t want to talk about wartime), and that means succeeding generations came to have less curiosity (due to fewer prompting comments). I figure, whatever we can learn (and tell) now, the more opportunities there will be.

      How fun, to find other relatives who know stories you don’t!

      Thanks for reading!

  7. Hi Julie, your stories and prompts are so much fun you could probably make a living drawing the stories out of others! And I know you have more, like the wedding cake story (included in “Paper Doll Interviews the Genealogy Organizers”). Thanks for mentioning my book! You are so right that this is a good time to be thinking about this, with holiday gatherings coming up. And yes, your mother’s first cousin is your first cousin once removed. 🙂

    • Julie Bestry says:

      Heh, maybe my next career, eh, Hazel?

      And I knew you’d verify my family history chart. I thought he was second cousin, but there’s something difficult when relatives are so far from you in age, and from distances, the connections seem vague.

      Your book is FABULOUS, so everyone should buy it and read it, no matter the depth (or shallowness) of their current interest in family history. I love how your book helps people adjust their actions in accordance with how much effort they want to put in.

      Thanks for reading and inspiring this post!

  8. Oh, Julie, you again delight me with your researcher’s mind and ability to formulate wonderful, insightful questions. Thanks for this. I hope all those people who are thinking of writing a memoir in their retired years will have the opportunity to read this post and the next one to help them orient their writing. Thanks!

    • Julie Bestry says:

      Aww, I’m blushing! And absolutely, these prompts should be a great catalyst for starting a memoir. (Next week’s suggestions should also be helpful for those who want to pen a memoir but need some outside motivation to capture the stories.)

      Thanks for being so supportive and reading the blog!

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