We recently had the chance to connect with Lesly Pyle and have shared our conversation below.
Hi Lesly , thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: Have any recent moments made you laugh or feel proud?
Cut to May 16, 2025.
I got laid off from an advertising copywriting job that I loved. Even though my spirits have stayed high, there have been moments when I felt like I had no value as a writer anymore.
Then along came Pauly.
Cut to June 11, 2025.
Paul Taylor of ADWEAK satire fame came calling. ADWEAK is like the Onion but for the ad biz. His LinkedIn posts are so funny because they’re so true. He slid into my DMs with an offer I couldn’t refuse — asking if I’d be willing to be his first-ever Field Reporter. Uh, yes, yes I will. I’ve got a few posts out there that are making some noise. People are laughing. People are commenting. And people are sliding into my DMs with potential paid writing gigs.
Can you briefly introduce yourself and share what makes you or your brand unique?
“Pyle of Memories” began humbly as simple short stories on social media all tagged with this message for friends: “#PyleOfMemories is a series developed for #DementiaAwareness as a reminder to write the good stuff down before it’s lost forever.” I started this because my grandmother had dementia and in one of her more lucid moments she asked me to write a memory about her. That was when it dawned on me that memories can disappear in a blink so I better start writing down the things I never want to forget. And I wanted to encourage others to do the same.
People started following the series and urging me to turn it into a book. So I did. But I didn’t have any desire to make a personal profit from it. I wanted to donate all the proceeds to dementia research. And to give it even greater fundraising potential, I got 35 fellow writers to contribute personal memories of their own. The book launched in September 2023 and became an Amazon bestseller (in the humor category) in the first week. Humor? Yes. Even though the subject may be sad, and there are some somber moments within the pages, most of the stories are funny. I love the balance. It feels more like real life. And that’s why I believe it’s been successful. The stories strike such a chord because they are so relatable.
In 2024, “Pyle of Memories” made its first donation to Lauren and Seth Rogen’s caregiving and dementia research foundation, “Hilarity for Charity.”
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What was your earliest memory of feeling powerful?
My earliest memory of feeling powerful came when I was 10 years old. Thanks to my Nonna Sarah and her idea of writing the good stuff down, here’s the first #PyleOfMemories social media story I ever posted. A decade later, it became chapter 1 in the book.
“Grandma Outlaw”
Cut to 2014.
My grandmother asked me to write a memory about her. A few minutes later, poof. She had already forgotten asking for it. She was suffering from dementia, and this was a rare lucid thought — one where she wanted so badly to remember the good stuff. But it got me thinking. And thinking. And it opened the floodgates to so many things I never would’ve written down without her request.
But before we get to my personal memory of a crazy moment my grandmother and I shared in 1988, I’d like to talk a bit about her. So here’s a few quick-cut flashbacks from my grandmother’s life. It spanned 95 long years but what remains actually makes for a pretty short story. While digging through my mother’s brain for the backstory section of this chapter, I learned that most of her mom’s history is still a mystery. And what she did remember was a slew of sad circumstances that her mother had to overcome. But my experience with my grandmother wasn’t sad at all.
In fact, it was anything but.
***
Cut to February 9, 1921.
My grandmother was born in the cozy coal-mining borough of Old Forge, Pennsylvania with ten fingers, ten toes and a ten-syllabic, beautifully-melodic name: “Saveria L. Caracciolo” [Sa-ver-ee-uh L. Ka-rach-ee-o-lo]. Her father, Matteo, grew up on the east coast of Italy in a town called Manfredonia in the province of Foggia. It’s just above the heel of the boot. He became a shoemaker. Go figure.
Saveria went by her American name: Sarah. Technically, it’s “Sara.” She added the “h” unofficially. No one knows why. But since I was young, I’ve suspected it was a silent, yet wonderful, rebellion.
Sarah was the eldest of nine children. She had two little sisters and six little brothers. But figuratively speaking, Mama(h) Mia(h), she was the one with the spiciest-a(h) meatballs-a(h) of all-a(h). [The silent “h” is in her (h)onor.]
Later, she would teach me how to craft real spicy meatballs from Italian sausage as well as Chicken & Dumplings from scratch — something my own mother absolutely despised making. Cooking skipped a generation. Well, at least until after my big brother, Eric, and I were long out of the house. Our mom ended up getting really good once she had time to learn. We’d like to thank our Bonus Dad Roger for giving our mom that opportunity when she retired. Her cooking is one of the many things we now enjoy when we visit their place. Our mom says that one of her greatest parental achievements was raising kids who actually want to come home. This wasn’t always the case for her. After leaving Indiana at the age of 18 to marry our biological dad, it was a while before she went back. But towards the end of my grandmother’s life, my mom spent quite a bit of time at her mom’s Indiana nursing home fighting the system for better elder care. Another thing we can thank Roger for — giving our mom more time for the things that matter most.
Like my mother, my brother and myself, my grandmother started working when she was very young. Using her own money, she splurged on a bottle of nail polish. She was so proud of how pretty her hands looked that she thought it would make her hard-to-please father proud too. But he was horrified. So much so that he said God would punish her for being so vain. Two days later, at 18, she suffered a horrific, on-the-job injury at a laundromat which left her left hand with only a thumb, a pinky and three stubs in between. But she never let that hold her back. She cooked, sewed, knitted, worked and went about life with a handicap that she never seemed to be aware of. I just thought it looked like she was always waving “hang loose.” And though she harnessed the friendliness of the aloha spirit throughout her life, she didn’t make it to Hawaii until well into her golden years. Money for travel was a thing of the imagination given all the mouths she had to feed. Like any stray animal lucky enough to cross her path. And later, her own children. One of whom, my mother, would grow up to support her two young children on her own by polishing nails as a professional Manicurist. Go figure.
As sad as it is to say this out loud, my grandmother’s Hawaiian trip was her only real vacation to speak of — and she had to wait until it could be funded by one of her grandkids. I wish I could say that was me but I just recently heard this story. As legend has it, my cousin and his mom had trouble keeping up with my giddy grandmother YOLO-ing all over the archipelago. Something about the tropical weather did wonders for her arthritis and she climbed every hill with ease and danced in delight every night as the sun set. The Islands must have been even more beautiful while she was there.
In 1943, Sarah Louise Caraciollo married Chester Carl Webb. I know even less about my grandfather’s life than I do about my grandmother’s. From what I gather, it seems he was pretty similar to my grandmother’s dad. Chester also had a hard life, was hard to please, and was just as hard to get to know. I think that’s why my mom didn’t talk much about her dad. The same is true of my biological father, Lester, who I am named after. (Our mom may not have been a great cook when my big brother and I were little but she knew how to preserve our innocence.)
Continuing her legacy of resiliency, my grandmother gave back-to-back births to stillborn sons. But she didn’t let that hold her back either. She had four more children who bore her nine grandchildren. My brother and I were the only two who didn’t grow up close to her. Literally or figuratively. Our grandmother lived in Indiana (by way of Pennsylvania). We lived in Oklahoma (by way of Oklahoma). And none of us had extra cash for flights (or long-distance calling when that was a thing.)
After her grandchildren grew up, Grandma Sarah asked us to start calling her “Nonna” to hold on to our Italian heritage. Come si desidera, Nonna. [As you wish, Grandmother.]
On August 16, 2016, we lost Nonna Sarah Saveria Caracciolo Webb to complications from dementia. She fought long and hard like she did her whole life but the disease ultimately took her from us just like it took her mind from her. But as you’ll see, her name, and this memory are still very much alive.
***
Cut to July 31, 2014.
I sat down to write the memory Nonna Sarah requested. But I realized, sorrowfully, that I don’t have many. I thought maybe I could write about how weird it was that she and I both bounced back from potentially career-ending hand injuries that we got at work. But that’s not really what she was after. It’s just a bizarre true story.
Growing up so far apart, and only seeing her like four times ever, made this one of my hardest writing assignments ever. Then boom. It hit me. It had to be when she came to Norman, Oklahoma for my mom and Bonus Dad Scott’s wedding. But this story has nothing to do with marriage. Unless you count bravery.
Below was my first #PyleOfMemories social media post — the memory that kickstarted my memories — which developed into a series for dementia awareness and is now a book for funding dementia research. Thanks for the idea, Nonna Sarah. And thanks for making this, and every other memory our family has ever had, possible. Your resilience — and surprising rebellious spirit — are truly things to be remembered.
***
Cut to April 21, 1988.
I was smaller than all the other students in my fourth-grade class. As a scrappy tomboy to the core, I didn’t let my size hold me back. My school, Eisenhower Elementary, was about to host their annual ‘89-er Day Celebration. This highly-anticipated children’s event reenacted the notorious Oklahoma Land Run of 1889 (where the infamous terms “Boomer” and “Sooner” were “born and bred” and still exist today in the eponymous University of Oklahoma’s fight song.) You might remember the Land Run depicted in the 1992 film “Far and Away,” starring Tom Cruise and Nicole Kidman? Well, in our version, 100s of kids, donning period-appropriate costumes, clawed their way across the schoolyard to stake their plots before anyone else. It was as competitive and vicious as the original.
In short, it was awesome.
My favorite part was picking a trade and dressing in character. I found most school subjects kind of boring but I was all in for any homework that encouraged creativity — especially if it meant I could pretend to be a bad guy. My fellow tomboy friend, Paula Peterson, and I chose to be outlaws. (God forbid we wear dresses like the other little girls. Like, who can run in those things?) Paula and I scrounged around her sprawling property on the remotest stretch of Rock Creek Road for the largest piece of cardboard we could find. Eureka! An old refrigerator box! This could easily transform into a cave fit for criminals! We spent hours spray painting it to look like the Devil’s Kitchen chamber at Alabaster Caverns — a landmark near the Oklahoma panhandle that Paula and I would later visit together. We may have gotten a little high from the paint fumes.
In short, it was awesome.
The next step was buying enough candy to barter for goods all day long which was required for ‘89-Day survival.
Enter Grandma.
We backed out of our humble home on Haverhill Circle in my mom’s blazing red 1978 Ford Granada. Grandma adjusted the bench seat a few inches forward so she could reach the pedals. We were off to shop for the most coveted of candies. Jolly Ranchers, Charms Blow Pops and Life Savers. Never chocolate. Even 10-year-olds know if you’re gonna have anything worth trading, your sugar selections have to stand up to the heat. (Summer starts in spring in the Heartland. So does winter sometimes.)
It was getting close to closing time as we headed down West Robinson towards Flood Street. I was nervous we wouldn’t make it to the store before the doors locked and my dreams of being “The Bad Guy with The Good Candy” would be killed. In retrospect, that should’ve been the least of my worries.
Enter an oncoming cargo train.
We simultaneously spotted the red flashing indicator light at an intersection that was known for backing up traffic. My intuitive grandmother, sensing my distress, tightened her grip on the steering wheel, white-knuckling all seven of her remaining fingers, jammed on the pedal, and outran the gate just before it slammed down. We got like five feet of air. (Which was taller than her!) Turns out, grandma was an undersized outlaw too.
Paula and I cleaned up at ‘89-er Day in ’88. We couldn’t have done it without Nonna Sarah. And this book couldn’t have happened without her either.
In short, she was awesome.
If you could say one kind thing to your younger self, what would it be?
I wish I had come to this realization so much earlier in life. But I live by it now:
“Don’t measure yourself by other’s successes or anyone else’s measure of success.”
I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What would your closest friends say really matters to you?
Them. I hope they know how much they matter to me.
Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What is the story you hope people tell about you when you’re gone?
When my time is up, I want people to remember that I lived by the lessons I learned in this moment: the most influential one of my adult life.
Cut to June 1, 2019.
2:41 p.m.
Click.
One Mississippi.
Two Mississippi.
Click.
I looked up to find the rhythmic sound’s source. It’s the unhurried cane of an extremely elderly lady crossing the street. No, this isn’t a setup to a joke. It’s something profound that actually happened to me.
Click.
One Mississippi.
Two Mississippi.
Click.
She’s managed to make it halfway. I’m not sure if she needs help but it’s a busy thoroughfare (as busy as it gets in the sleepy San Francisco surburb of Dublin, California, anyway.) So I offered her my arm. She snatched my hand with the strength of nine nonagenarians.
Click.
One Mississippi.
Two Mississippi.
Click.
At last, we made it to the other side. There’s a neighborhood park with a 1/4 mile walking track, a playground and a mini dog run. Perhaps she’s headed to the annual Corgi Con happening today, I wondered. I saw a woman sitting on a bench inside the Canine Corral consoling the only dog that didn’t fit in. She looked up from her sulking Schnauzer and locked eyes with me. We studied each other’s situations with a smirk of solidarity. I can only imagine what she must have thought. What a sight the two of us must have been. Me, a conspicuously undersized and overly-pale girl of ambiguous age having just come from the pool — wearing only a bikini. Her, an incredibly dark-skinned Indian woman with a vice grip on my fingers who was fully-shrouded in a sari — and even shorter than me.
Click.
One Mississippi.
Two Mississippi.
Click.
Slowly, we left Corgi Con and Tormented Terrier in our wake.
Click.
One Mississippi.
Two Mississippi.
Click.
I had no idea where this woman was going. I just trusted that when we got there, she’d let go. So we kept on in silence, with only the sounds of a clockwork cane and oddly-proportioned dogs barking in the background. We walked without words, fully aware we didn’t share a common language. Not a verbal one, anyway.
Click.
One Mississippi.
Two Mississippi.
Click.
After a half hour of inching counterclockwise around a loop that I can do in five minutes flat, we circled back, hand-in-hand, to the crosswalk where fate brought us together. There’s a 55+ Senior Center on the other side. Surely that’s where she lives? No. We pass it by.
Click.
One Mississippi.
Two Mississippi.
Click.
She pointed with her cane to turn left. We crossed the gate to an elevator where a few residents were also boarding. They patiently waited and held the door open as it beeped angrily. They asked where we were going. I told them that I had no idea. When they realized we didn’t know each other, they asked if the woman was lost. I said that I wasn’t sure but I was letting her lead the way. The old woman tightened her grip as she leaned in close enough to the see the elevator buttons and pointed at the top floor with her nose. I was losing circulation. But not hope. A young lady pressed the button for us. Once we ascended, the others scattered with the quickness of youth, not wanting to get involved in what seemed to be a case of dementia. So the two of us were left standing at another crossroad. She contemplated. And chose a direction without any real confidence. But she led me leftward to the end of a long walkway. Which led to another long walkway. That’s when she let go of my hand, looked up at me for the first time, smiled toothlessly, and patted me on my now-sunburned back.
I stared down that long, dark, lonely hallway.
There was no way I was just going to leave her there.
Click.
One Mississippi.
Two Mississippi.
Click.
With the hand that had once held mine so tightly, she used the wall to steady herself. I walked with her to the last door, again on the left, as she draped her shawl over her head. She turned the nob and opened the unlocked door. Her family stood up from their sofa in silent unison. I’m not sure if it was as a sign of respect or relief. Maybe both. But I asked if she belonged to them, and they simply nodded “yes” in appreciation. I wept, overcome with emotion, wondering if I rescued her. Or if she rescued me. Maybe both. I walked away at her pace thankful that I knew the right way home. All right turns. A metaphor that was not lost on me.
Cut to the present moment.
Not a day goes by that I don’t think about how a nearly-blind perfect stranger helped me see the light. There are so many precious moments to be had if you slow down long enough to appreciate them. So count your Mississippis, my friends. Time is a blessing. And there’s no better way I could have spent mine that day.
Contact Info:
- Website: https://www.pyleofwords.com
- Instagram: @pyleofmemories_book
- Linkedin: https://www.linkedin.com/in/friscomoon/
- Other: Paul Taylor’s hilarious ADWEAK page:
https://www.linkedin.com/in/paul-taylor-ab2721163/
Image Credits
Book + Creator Image: TRG Studios
Nonna Sarah photo collage: Photographers unknown
