Bridging the intergenerational divide

An afternoon of conversation and connection across ages.

The holidays can be a wonderful time to enjoy the company of loved ones. But for people who experience loneliness, social isolation, or social anxiety, the holidays can instead be a source of compounded sadness or stress.

Unfortunately, many people feel this way. The Economist recently reported that 22% of adults in the U.S. “always or often feel lonely, or lack companionship, or else feel left out or isolated.” Other surveys have estimated that loneliness affects nearly half of Americans. As a result, people may develop health consequences similar to those caused by smoking and obesity.

When I moderated a panel on this topic earlier this year, one takeaway was that intergenerational connection can be a meaningful way to counter loneliness and foster social health. I’ve been interested in exploring that idea ever since, and the holidays seemed like the perfect opportunity.

Facilitating connection

So in December, I hosted an Intergenerational Friendship Pop-Up with my fellow World Economic Forum Global Shapers in San Francisco. We brought together fifteen millennials and fifteen “perennials” (as Marie Jobling, executive director of the Community Living Campaign, calls seniors) for two hours of conversation and connection.

The outcome was beautiful.

Designed and led by Ivan Cash and Scott Shigeoka, the interactive experiences began at the door. Participants walked in one by one, picked up a handwritten note, got a 30-second portrait painting done, and contributed herbs and spices to a large pot of hot water.

Once inside, participants sat in a circle, shared their names and motivations for coming, and paused for a moment of mindfulness breathing. Then Scott assembled millennial-perennial pairs by randomly matching two portrait paintings.

That was when the real magic began.

Ivan guided the pairs through a series of prompts that bypassed small talk, such as, “Share your life story in four minutes,” “Describe a challenge you are currently facing,” and, “What is one thing you are especially proud of?” Over the course of an hour, I watched people who had never crossed paths before open up to one another, discuss personal experiences, find commonalities, empathize, laugh, and even cry.

Lastly, everyone came back together in a circle to reflect as a group. One pair had discovered that they both grew up within a few miles of each other, albeit during different decades. Others shared what they learned from their partner or how the conversation differed from their normal interactions.

“I was amazed that we had so much in common.”
“She reminded me of the excitement I felt when I was her age.”
“I came in as a stranger not knowing anyone. I’m leaving here with a friend. And all it took was conversation — I didn’t even have to bake her cookies!”

Participants clearly enjoyed exchanging perspectives and wisdom across the age gap. But I was also struck by how much people appreciated the chance to connect on a deeper level, period — regardless of age.

“I’m surprised by how little space there is in my life to have conversations that are so human with anyone. If this was the norm, we would feel so much more connected. I’m wondering why I don’t even ask these questions with my existing friends.”
“We could all practice more active listening in our day-to-day lives.”

Overall, it was gratifying to see the experience unfold and hear people’s reactions. When I first envisioned the event, I hoped participants would walk away having had a meaningful conversation with someone they wouldn’t otherwise have gotten to know, thought about age differences and human connection in a new way, and learned to see strangers as neighbors or potential friends.

And that’s exactly what happened.


We were intentional about capping the event at 30 participants and limiting the number of volunteers on the sidelines. I think this choice was crucial, because it kept the environment intimate and made it safe for people to be vulnerable.

Another successful element was infusing ritual throughout the event. For example, everyone helped make and later drank communal hot tea, and we convened as a group at both the start and finish. Ritual served to anchor people around shared actions, while symbolizing unity and community.

Interestingly, we gleaned an insight about marketing to different age demographics. With just a few social media posts, we filled the millennial spots within two days and ended up having a wait list.

But for perennials, raising awareness was challenging. We tried targeted Facebook ads, outreach to local retirement residences and senior organizations, and posting flyers at coffee shops, community centers, and churches. None of those tactics worked well. The most reliable source of perennial sign-ups ended up being personal invitations to second- and third-degree connections. Perhaps having a trusted source who could provide more information was the key.

New year, new connections

Opportunities to bridge generations and improve our social health don’t stop once the holidays are over. Here in San Francisco, 180,000+ residents are over 60 and many are socially isolated due to mobility restrictions. It’s likely that 43% are lonely. With around 300,000 millennials in the city who are even lonelier, that’s a lot of possibilities for new friendships.

As we head into 2019, consider making a resolution to introduce yourself and develop a rapport with at least one elderly or younger neighbor. And if you’re looking to exercise your social health with friends, family, coworkers, or strangers of any age, I recommend The And cards for conversation prompts. If you try it, let me know how it goes!

Special thanks to Caroline Gutman for the photos, Ivan Cash and Scott Shigeoka for designing the interactive experiences, and my fellow WEF Global Shapers for helping organize the event.