At Operational Planning 2026, Jack York reminds us of the powerful stories contained within us all
As the first keynote speaker to take the stage at the annual Schlegel Villages Operational Planning Retreat in Niagara Falls in early October, Jack York touched upon something immensely personal early on. He spoke about the death of his mother as a catalyst for the path his life up to now has taken.
In the late 1990s, Jack was remarkably successful in California’s emerging Silicon Valey tech world, and he and his team donated computers to a senior living community in Southern California. At the time, he didn't imagine this would become a business or change the direction of his career.
He explained to the Schlegel conference how six months after that computer donation, his family celebrated his mother's 80th birthday, and how awful it was that she died from a massive stroke just eight hours after the celebration.
Jack described his mother’s death as both tragic and joyful in an odd way. He was financially successful, but he felt this work wasn't feeding his soul, so the aftermath of her death, he chose to leave that world behind and do something that made a difference.
That decision led him to establish IN2L (It's Never Too Late), which developed technology to enrich the lives of older adults. The company eventually grew to serve thousands of communities across North America, and Schlegel Villages was the first to adopt it in Canada.
“This is really a circle of life moment for me, being right here with you guys,” he explained, adding that the next hour of his discussion was about what he has learned since he made the choice to focus beyond the power of technology to the power of human connection.
His journey with IN2L eventually led to his latest venture, TaleGate, which has seen him travel a few hundred thousand miles across North America in a van, venturing from community to community, meeting older adults and listening to their experiences. Along the way, he encountered a former tap dancer who hadn’t danced in 35 years, a quiet Vietnam veteran who came alive when he spoke about his time as a drill sergeant, and people whose seemingly small habits revealed much deeper stories of love, loss and resilience.
Each encounter was a reminder that there is so much more to a person than what we see upon first glance, which is a message that feels at home in Schlegel Villages. Though more than 10 years of our #ElderWisdom campaign and our ongoing commitment to storytelling, we’ve been working to celebrate the experiences, wisdom and individuality of the people who call our Villages home. 
We know that every resident has lived a life full of moments that have shaped who they are, and that sharing those experiences can bring us all closer together.
Jack is a likeminded friend who reminds us why this work matters.
His own path was shaped by the loss of his mother and the questions he never asked his father, who among other worldly adventures had been shaped by his service in the Second World War. There are so many questions Jack wishes he had asked his dad; today he asks those questions of others, and he’s learned a key lesson in the process: ask a question, then be quiet and give the person time to answer.
Don’t rush to fill the silence. Don’t finish their sentences. Don’t assume you know the story.
Sometimes, the most meaningful moments come when we slow down enough to let someone share a memory they haven’t thought about in years, or discover something about themselves through the act of remembrance and sharing.
Jack has also seen how stories can help us connect with people living with dementia. Rather than focusing only on what someone may have lost, he encourages us to meet people where they are, finding connection through music, familiar experiences and the feelings that remain.
The impact reaches beyond the specifics of what a person sharing. When we hear someone’s story, we begin to see them differently. We understand a little more about who they are, what matters to them and the experiences that have brought them to this moment.
That’s the beauty of storytelling. It builds bridges between generations, strengthens relationships and reminds us of the person behind every role, diagnosis or assumption.
There are so many stories waiting to be heard across our Villages and we’re always looking to tell more.
Jack’s message is a timely reminder that Schlegel Villages is on an important path and that as we grow, we must stay connected to our stories. We don’t always need a special program or a grand gesture to make a connection. Sometimes, all it takes is a little curiosity, a good question and the willingness to listen.
- Previous
- View All News
- Next
