Best Results Organizing

Last week, in How to Collect, Organize, and Preserve Family Memories and History (Part 1) — The Questions we looked at why you might want to collect family memories and stories.

It’s easy to think that it’s all about “genealogy,” which can seem like a dry topic to those who haven’t delved into wacky and wondrous family stories. But we saw how embracing family history can do more than clarify what’s happening in family photos (or make those strangers in black-and-white come alive and feel more three-dimensional). Family stories can help tether us to a genetic continuum and weave us into a tapestry going back generations and extending broadly across time and locations.

For example, when I started my business, I felt like I was adrift, the first person to really “start” a business. When asked for her profession, Paper Mommy usually puts down “part-time brain surgeon” for fun, and while motherhood is an intellectual and physical triumph, it doesn’t ecacly bring in the Benjamins. My father was an attorney and judge, but in the late 1940s, he joined an already existing practice.

But focusing on those stories I told you last week, I can place myself along a continuum of business owners: my material great-grandfather owned his own bakery (with my great-grandmother, who ran it); my paternal grandfather, who co-owned a tailors’ notions shop; my maternal grandfather, who traded in scrap metal (though decommissioned battleships seem more grandiose than “scrap” would imply).  

Last week’s post also detailed a wide variety of questions to help get conversations started about family history and memories. We know that some people (and some generations) find it hard to talk about themselves, so it’s no surprise their children don’t ask questions; they don’t realize there’s anything to ask! Hopefully, the prompts I provided last week will give you a starting point to talk with your family about the rich tapestry of their lives.

But what will you do with these stories once you’ve gathered them, and how will you preserve them for future generations?

Incorporate family photos into their stories

Explore creative options for collecting family memories

The above options are more familiar, straightforward approaches to getting your family to tell stories and capture them, but if your family is up for some adventure, try something atypical.

This summer, I was intrigued by Perfect Pixel Moment‘s blog post on Medium, 12 New Ways to Preserve Family Memories, which included ideas like creating a family podcast series, developing a family blog, producing multi-generational family cooking videos, and more. Check it out.

What to do with what you collect

What you do with the notes, audios, and videos you capture is up to you. As with tangible organizing, you have to sort, merge, and edit your specific categories before organizing things into final form.

Whether you share raw footage or edit everything into a meaningful presentation, a documentary, or private YouTube channel is your choice. For now, focus on gathering and preserving the information while your storytellers are with you and up to the task of narrating their rich histories.

PLATFORMS FOR CAPTURING FAMILY MEMORIES IN BOOK FORM

There a huge number of services and apps designed to help you collect, organize, preserve, and share your family’s memories. The rest of this post explores just a few.

Storyworth

Storyworth is a subscription-based service. You select a weekly email prompt from the database of hundreds of “tell me about your life” questions. Your recipients respond with their own emails.

Unlike the broad, overarching prompts I suggested in last week’s post, Storyworth’s questions are more pointed and varied, including, “Can you sing your favorite lullaby?” and “What is one of your greatest fears?” (You can also edit the suggested questions or use your own.) 

Stories are private by default and available to download by only authorized family members. At the end of the year, the responses to the prompts are bound into a book.

A standard package includes a year’s worth of weekly story prompts to help you interview one “storyteller,” online access for an unlimited number of family members (as authorized by you), and one 6″ x 9″ hardcover book with a black & white interior and a full color cover.

You can’t apply any of your own formatting, change fonts, etc., but the books can include photos. (The storyteller attaches photos to their email responses.) Once the responses are submitted, you and/or the storyteller can log in and edit responses and add captions to the photos, though some online reviews have mentioned the editing process can be finicky. 

Extra books can be ordered, as follows:

• $39: Black and white interior, up to 480 pages
• $79: Color books, up to 300 pages
• $99: Color books above 300 pages, up to 480 pages

If you purchase multiple subscription packages, you can opt to blend multiple family members’ stories into one book.

A package is $99 for a year, with domestic shipping included.

Founded by Nick Baum to capture his father’s stories, Storyworth is independent and family-owned, and has been in business for over a decade. 

Storyworth is best suited for a loved one who is comfortable with technology, in good enough health to read on-screen prompts and reply on their own, and eager enough to overcome procrastination or inertia and respond to a weekly email.

You know your relatives best. Will they feel like this is homework to slog through or an opportunity to shine?

Because stories are captured in print form (even with photos), they lack the vividness of platforms with audio and/or video. However, history tells us that print books will always be accessible, while digital A/V formats quickly become obsolete.

My Life In a Book

A similar biographical approach is offered by My Life in a Book, with questions selected from a database (though you can create your own questions to reflect the uniqueness of your relatives’ experiences).

Prompts come to your recipient via email, and replies are returned similarly, though there is a voice-to-text option, which allows someone to narrate stories directly into the online system.

Additionally, unlike the weekly flow of Storyworth, My Life in a Book allows you to customize the frequency of the arrival of the questions. Chatty Cathy can get them faster; Silent Sam can be asked less often.

This platform has a more structured biographical approach, with themes for the books:

• Preserving Memories fits the theme of tracking the lives of parents and grandparents
• Baby’s First Moments preserves important memories for new parents
• The Story of Us helps couples track their lives together
• I’m Writing a Book About You lets you create a book for and about a special loved one

My Life in a Book offers collaborative editing, so both the storyteller and any family members with access can help edit responses and even add photographs. You can also get real-time notifications to update you when your loved one has responded.

Users have input into the final book, including selecting from a variety of cover designs, choosing from a palette of color themes, and choosing different cover font text (but not interior fonts). Depending on the selected style, you may either select a pre-designed image or use a custom photo.

My Life in a Book is also $99, and shipping of books is free domestically and to Canada, UK, Australia, and New Zealand; there are shipping fees to other countries. Upgrades (at additional cost) include audiobook versions, additional print copies, and gift boxes for print books.

Remento

Remento is a worth considering if your loved one might feel more comfortable narrating a story rather than typing it.

There are still weekly prompts (which can include user-provided photo prompts), but the storyteller speaks the response into the system using a smartphone or computer; there are no logins or downloads, and reviewers report that it only requires a few clicks to get started.

Remento records and transcribes the recordings into stories printed as hardcover books.

Additionally, the books are printed with QR codes, which, when scanned, play the original recording used to write the chapters. Thus, future generations not only get the book, but get to hear the voice of the storyteller (at least as long as Remento is in business).

Remento uses artificial intelligence. Once the narration is recorded, you get to choose your preferred writing style (first-person, third-person, or transcript). From there, Remento’s Speech-to-Story™ AI technology turns your storyteller’s voice into a polished, edited written narrative. You can also customize the book’s title, color, and cover photo.

Remento is currently priced at $99, for which you get unlimited prompts and recordings, unlimited collaborators, and one premium, color-printed book. (If you subscribe to their mailing list at the bottom of the front page and are willing to get updates and notifications for sales and giveaways, you get $10 off.)

Remento is a little more focused on the journey (involving the whole family in encouraging responses to the prompts) than the destination (creating a book). All authorized family members can collaborate, watch the recordings as they’re submitted, send reactions to what’s been created (thereby providing the family storyteller with positive feedback), and select new prompts for future use. 

As with the above options, your loved one will still need to keep up with prompts to get value, but the easy audio interface may make the experience more inviting than having to reply in writing.

Getting reactions on each uploaded story may be a positive experience (like getting a thumbs-up “like” on Facebook) or might be distracting and yield self-consciousness. 

MULTIMEDIA PLATFORMS FOR PRESERVING FAMILY HISTORY

Books are fabulous, and your great-great-great-great grandchildren will probably be able to read text, as long as it’s not written in cursive. But if you want your family’s memories to come alive, and you want your own grandchildren to feel like they really knew your grandparents, there’s no substitute for audio and video.

StoryCorps

StoryCorps is a grand-daddy (or grand-mommy) of preserving family legacies, dating back to 2003, but it comes at it from a different perspective from most other platforms.

StoryCorps is a nonprofit project founded by a public radio producer, committed to the notion that we all have important stories to tell and that ALL of our stories matter. StoryCorps mission is to “help us believe in each other by illuminating the humanity and possibility in us all — one story at a time.” 

I have a lump in my throat just reading that!

StoryCorps has a collection of more than 700,000 stories, the largest archive of its kind. Rather than creating a recorded family history for just generations of your people, you can create a story for future generations of people all over. 

You have a few options for creating stories:

• Record with StoryCorps’ self-directed tools. If you can get in the same room with your loved one, use the StoryCorps App. Use my prompts from last week’s post, invent your own, or use StoryCorps’ prompts — then ask away. Alternatively, if your loved ones are elsewhere, whether across the city or across the world, you can record stories together via your web browsers using StoryCorps Connect. Either way, you can preserve your conversations using StoryCorps DIY resources.

• Alternatively, you and a loved one can record a conversation at one of the StoryCorps recording sites with the help of a facilitator. This adds a nice professional layer to the question-and-answer experience and may help your loved one feel more inspired. At the end of the session you get a recording of your interview and a copy is sent to the American Folklife Center at the Library of Congress. Talk about legacy! 
  • StoryCorps Mobile Tours — Each year for the last 15 years, StoryCorps has been going on a nationwide mobile tour. As I was writing last week’s post, I just happened to learn that they’re just up the road from me in Knoxville, TN, through the end of the month!
  • StoryCorps Atlanta Booth — The StoryCorps facility at the Atlanta History Center has recorded and preserved thousands of conversations since 2013. If you’re in or near Atlanta, book an appointment to “interview” your loved one in person or even virtually, by phone. (They can feel like they’re on NPR, being interviewed by Terry Gross or Mary Louise Kelly!)
  • Military Voices Initiative — This program provides a way for service members, veterans, and military families across America to honor and listen to their loved one’s stories. Book an appointment to preserve their memories (and your questions) in person or virtually at one of their Military Voices Initiative stops.

Some segments may even air on NPR, and I’ve seen beautiful StoryCorps personal histories set to animated video on StoryCorps’ TikTok channel. In fact, the following video prompted this part of the post series.

For more stories, see StoryCorps’s archive and YouTube page.

StoryCorps is free to all users.

Obviously, StoryCorps isn’t the right option for capturing an entire lifetime of memories, let alone the stories of all of your loved ones. However, the professionalism of the production experience may inspire your family members who may be dubious about having something to say, or who are shy about sharing their stories, to open up a bit. Consider StoryCorps as a way to delight in the storytelling experience and use it as an on-ramp for refreshing memories.

STORII

Storii recognizes that not everyone is going to be comfortable with typing their stories or even clicking around on an app or website. It’s designed for Great-Grandpa, who grunts at computers and cell phones whenever he sees them in public. (And for folks who, for whatever reason, have difficulty with technology.)

Storii uses actual phone calls to collect memories. Unless Great-Grandpa predates Alexander Graham Bell inventing the telephone in 1876, I think you’re safe.

Set up an account profile (in Storii’s iOS or Android app) for your loved ones to receive phone calls, whether on a cell phone or landline; alternatively, they can call in. (No smartphone or internet is required.)

Next, choose prompting questions from more than 1000 life story questions in their database (broken down into guiding categories like life, family, religion, career, or legacy), and/or craft some of your own.

Schedule up to three automated incoming calls per week at a time you know is good for your loved one, or arrange for them to call in to record their responses. Storii records and transcribes the calls, and adds them to your profile.

Record interactive responses. You and other family members can listen to the recordings and respond with audio, video, photo, and text responses.

Access the recordings as audiobooks or downloadable PDF books. Recordings can be shared with other family members by secure links or via emails. 

If you think your storytellers won’t be at ease if they’re “surprised” by a question (even on a scheduled call), there are a few options.

They (or you) can log in to their Storii profile to see all upcoming questions (and remove, re-order, or add custom questions). If your loved ones don’t have (or don’t want to use) internet, and aren’t keen on getting you involved, they can call in to Storii at any time to hear their next upcoming question.

They can also just hang up after they hear the question on the scheduled call, and Storii will keep asking the same question until it’s either answered or skipped.

Storii’s pricing is $9.99/month or $99/year.

We have just scratched the surface of the DIY options and formal platforms for capturing, organizing, and preserving your family’s stories. But Paper Doll has one more trick up her sleeve. Next week, we’ll close out this series with AI-assisted platforms and apps for creating those family legacies. See you next time!

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.

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.