The Picture Gets Sent. The Conversation Stays With Me.
At a New York City yard sale, someone stops at my Boomernology table and pulls out a phone.
“Can you show me how to send this picture?”
A few minutes later, the picture is on its way.
Twenty minutes later, we’re still talking.
About how they came to New York City. Where they worked. The children they raised. The neighborhood they’ve watched change around them.
The phone has given us a reason to talk. And once we get going, there’s a lot more to talk about.
That’s one of my favorite parts of setting up at these neighborhood yard sales.
I find a spot between tables covered with records, books, lamps, and dishes. People browse. Neighbors catch up. Someone is deciding whether they have room for another chair in a New York City apartment.
An ambitious thought.
And there I am, with my Boomernology table, meeting people I might otherwise pass on the sidewalk.
Some have a tech question. Some want to know what I do. Some stop to say hello.
I never know where a conversation will go.
That’s what makes it worth having.
We spend so much of the day moving toward the next thing. Another appointment. Another errand. Another message we need to answer.
Even helping someone can become something we try to finish quickly.
We fix the setting, hand back the phone, and get on with the day.
I understand that. I’m running a business in New York City. I have places to be, too.
But I’m grateful for the times when a small question turns into a longer conversation. When I get to hear something I wouldn’t have learned if I’d packed up the moment the problem was solved.
The picture gets sent. The conversation stays with me.
It stays with me when I’m visiting clients, too.
I might arrive to help with email, a printer, or a phone that suddenly looks different after an update. While we work, we talk. I learn what matters to them, who they want to hear from, and what they’ve been trying to do.
Those details help me understand why the problem matters.
A family group chat is where the grandchildren send pictures. A video call is how an old friend in another state stays close. An email may contain an invitation someone has been looking forward to.
When something stops working, a little part of everyday life gets harder to reach.
And when we get it working again, there’s somewhere to go. Someone to answer. Something to share.
That’s why I care about how a person feels when I leave.
I want the phone to make sense. I want the printer to print.
I also want the person to feel comfortable calling again. To know they can ask a question without apologizing for it.
There’s a kind of trust in asking someone to sit beside you and help with something you don’t understand.
I try to remember that.
I also try to remember how much the person beside me knows.
The people I meet have built careers, raised families, cared for loved ones, and found their way through changes I may know nothing about.
They have stories. Opinions. A sense of humor. Entire lives that won’t become visible if all I look at is the screen.
Today, I know where the button is.
That gives me something useful to offer. Taking the time to listen gives me a chance to learn something, too.
This is part of what I love about Boomernology. I get to meet people spanning generations and spend time with them. We have a task to work on, but we also have a chance to get to know each other.
And sometimes a little humor makes the whole thing easier. You can be frustrated with a phone and still laugh with the person sitting next to you.
I think we could all use more moments like that.
A conversation with room for a story. A question we feel comfortable asking, a few minutes when someone is paying attention, and we don’t feel rushed.
At a neighborhood yard sale, those moments come naturally.
You stop at a table. You ask about something. You discover a shared memory, a familiar place, or a person you both know.
The neighborhood becomes a little more familiar because now you know one more person in it.
That’s what brings me back.
I’ll be at the 104th Street Block Association Yard Sale on Saturday, October 3rd, from 10 am to 5 pm. You’ll find me at the Boomernology table on West 104th Street between West End Avenue and Riverside Drive.
Bring a tech question, share a neighborhood story, or just stop by and say hello. I’d love to see you.
I’d love to hear your story.
— Dave

