We measure time in many ways. We measure it in the last time I saw you, the last time we spoke. The space between those moments grows into “it’s been too long,” until one day you realize you can’t remember the last time at all.
Too often, we don’t get to say what needs to be said to the person it belongs to. We begin to understand the space between time only when time is up in this lifetime.
This weekend, I attended a celebration of life for a woman who was many things to me—boss, co-worker, colleague, mentor—but most importantly, a friend.
Since 1984, Lillian was a part of my life. That’s a long time, more than half of it. I was a twenty-two-year-old just out of college, and the bank was my first real job. Lill was instrumental in my development—not just from a career standpoint, but in learning how to be an adult. The bank was a family, and I don’t say that lightly. Lill was the matriarch, sitting quite literally in the middle of it all, in the main lobby, as Senior Vice President. I watched the way she interacted with customers—with warmth, with grace, with a kind of presence that made people feel seen.
As I reflected yesterday, I started thinking about circles.
Our First Bank of Highland Park circle was one of the closest-knit groups I’ve ever been a part of. A lot of us grew up together inside that circle. We ate lunch together—small groups of two or three—back when long lunches were still a thing. Kountry Kitchen, Little Szechwan, J.B. Winberie’s. Drinks after work made us regulars at Winberie’s and The Wooden Nickel in Highwood. We had a basketball team, a co-ed softball team.
I started playing golf only because one of the Vice Presidents—and a few others—would leave the bank at 2:00 on warm Tuesdays and Thursdays to “survey some property.” One day he told me I needed to get some clubs and asked me where I thought they were really going.
And during those years, when the city of Chicago felt electric, four of us shared season tickets to the Chicago Bulls from ’91 to ’93. Those championship runs weren’t just about basketball—they were about who you experienced them with. Nights filled with noise, belief, and the kind of joy that only comes when you know you’re witnessing something special, together.
I think it was around ’87 when Lill invited me to join her poker group. We played once a month, rotating houses. Truth be told, it was more about the food and the conversation than the low-stakes card games. That’s the group in the picture above, it was the 25th anniversary of their group playing so we flew to Vegas for some real gambling. That’s Lill, second from the right.
Some of my fondest memories were when it was Lill’s turn to host. I’d get there early, before everyone else, sitting with her at the table, sipping tea—long before “sipping tea” became a thing people joked about. Just the two of us, talking about life, work, people. Nothing rushed, nothing forced. Just time, shared without knowing how valuable it would become.
That ritual lasted more than thirty years and ended over something petty. I don’t know what happened to the rest of them, but Lill and I stayed friends.
The circles within the circle of life. A big Venn diagram of shared relationships and experiences.
And then I started thinking about those circles a different way.
Like tires on the 18-wheeler of your life. Each tire its own circle, rotating on its own axis, serving its own purpose, but all necessary for the journey. They move independently, but they’re all carrying the same load—you, your life.
Tires go flat. Some blow out. Some just wear down over time and get replaced. But some… some last the entire ride. Family. Close friends. The ones you don’t discard—you patch them, repair them, keep them rolling.
And too often, those are the ones we take for granted. We don’t check them regularly. We forget they’re there until there’s a slow leak, or until they hit a nail, or the tread gets too low from neglect.
If the First Bank of Highland Park was a wheel, Lillian Herter was the hub. At least for me. But if you knew her, you’d probably say that for a lot of people in that circle.
A celebration of life has a way of bringing all those circles together, if only for a moment. Time expands, and in doing so, it creates space. The distance between phone calls and text messages grows. The gap between lunch and laughter widens.
I want to do a better job of checking my circles. Kicking the tires, so to speak. But more than that, not letting time rob me of the people who matter most—the ones who shaped me, the ones who are part of my foundation.
Because space can be narrowed.
Sometimes with something as simple as a text—
Thinking of you.
Or, Do you remember the time…
In memory of Lillian Herter.