Somewhere between holiday conversations and quiet moments, I realized my mom wasn’t just a storyteller — she was a listener, too.
We spent this past Christmas break with my mom. Every year, my wife, daughter, and I head down to Florida for the holidays. My mom loves having a full house, especially when it means extra time with her granddaughter. We enjoy the sunshine, the slower pace, and my wife and I really enjoy unplugging for a week.
Most years, the rhythm is familiar. We hang out around the house. My daughter hears stories about my mom’s childhood growing up in Sri Lanka in the 1940s and ’50s. My mom catches up on everything happening in my daughter’s life. The conversations flow easily across generations.
But this year felt a little different. I found myself doing a lot more of the talking.
Many of our conversations revolved around my daughter’s thoughts about life after high school. She still has more than a year before she needs to decide anything, and I’m perfectly comfortable with her answer being “I’m not sure yet.” The older generation, however—including my mom—had more questions. And somehow, those questions kept circling back to me.
Before I knew it, I was sharing stories from my own past: how I chose where to go to college, why I picked my major, what drew me to certain jobs, and why I moved around so much in my twenties.
What surprised me most was how much my mom enjoyed hearing these stories.
Some of them she knew pieces of, but not the full story. Like the summer after my sophomore year of college when I stayed on campus to take summer classes. The extra credits helped, sure—but the real reason was that I didn’t want to spend the summer at home, and summer school felt like my last escape hatch. Or the mystery of why my car always seemed to be full of sand in college—not because of some elaborate prank, but because we’d road-trip to the Jersey Shore on Saturday afternoons, then head straight to Atlantic City. We’d change clothes in the car. The sand stuck around.
Other stories she was hearing for the first time. Like the time I quit my tech job and disappeared to the Bahamas for a couple of months, including a solo ten-day kayak camping trip through a remote marine park. Or the three months I spent Jeeping through Colorado, New Mexico, Arizona, and Utah a few years later. These are not the kinds of stories you casually tell a mom who still says “be careful” when her 55 year old son goes out to buy groceries.
As I watched her listen, laugh, and ask questions, something clicked for me.
The original motivation behind Self Told was simple: I wanted to capture my mom’s stories before they were lost—before memory faded, before time took its toll—so they would be preserved for me and for my daughter. I had been so focused on my mom as the storyteller that I hadn’t fully appreciated her as a listener.
But of course she is. Human connection doesn’t flow in just one direction. Stories matter at every age.
When we’re all together around the table, listening to stories is effortless. But once we left Florida, I had to be honest with myself. No matter how simple I try to make Self Told, I don’t realistically see my mom opening the app on her tablet, logging in, browsing a growing list of stories, and deciding what to play. Even with bookmarks. Even with saved passwords. Even with the best intentions.
That friction matters.
If Self Told was going to truly serve my mom—not just as a place to record stories, but as a place to enjoy them—I needed to make listening as easy as sitting around the table.
That’s when the idea hit me: what if Alexa could play Self Told stories?
My mom talks to her smart speaker all the time. More often than I ever expected. What if listening to a family story was as simple as saying, “Hey Alexa, play me a Self Told story”?
No logging in. No browsing. No decisions. She could be cleaning up the kitchen, sitting on the couch with a cup of tea, or winding down for the evening. A family story would always be just a simple voice request away.
That realization led to the creation of the Self Told Alexa skill. Alexa plays stories from your account—and only your account—and chooses one at random each time, turning listening into a small, delightful surprise.
Self Told started as a way to preserve stories. But it’s growing into something more meaningful: a way to keep families connected, not just through recording memories, but through listening to them—easily, naturally, and often.
And it turns out my mom helped me see that.
