Remembering My Classmate, Jill Hennessy Shea (1973-2025)

Less than two months ago, I spent time in my beloved hometown in Columbia, Tennessee — about 35 miles south of Nashville — with high school classmates who were able to attend our 35-year Columbia Central High School (CHS) reunion.

All of us in our particular “Class of ’90” / Gen-X age cohort are in that infamous “sandwich” generation – juggling our lives and often the lives of the generations both ahead of and behind us.

Some of us still have kids at home. Some have long since also had grandkids. Many have aging parents with increasing care-giving needs of their own. Coupled with those demands are our own busy work schedules and careers. With all of the responsibilities and the daily intensity of our “sandwich” generation lives, it’s very easy to understand why it’s challenging to attend a high school reunion, particularly for those of us living many hours or numerous states away.

With all of that said, I’ve also become very aware of how many in our age group sometimes struggle with health challenges of our own – some of them quite serious.

It was for this reason that I felt especially motivated earlier this year to be sure we had our 35-year reunion, even if on a modest scale. The past number of years have reminded me all too often just how fragile life is. I’ve also received plenty of reminders myself that I’m no longer on the generous end of the age range considered to be “the younger generation.”  Anything can happen, anytime.

For those reasons, I kind of slapped together a modest high school reunion event this past September, as a self-appointed volunteer. I just felt called to do it.

My main focus was on a very informal gathering, simply for those of us who could attend to visit and catch up. No band or DJ. No printed invitations (Facebook is our only database). No decorations. No fancy name tags with our 35-year-old CHS senior year portraits also printed for the proverbial “then and now” reminders of our former selves.

During this past summer, after the date had been set and broadcast on our Class of ’90 Facebook group page, I texted a number of classmates who were out-of-towners like me, just to be sure they saw the alert about the event and could plan on attending, if schedules permitted.

One of these friends on my list to text was one of our classmates living in Florida who maintained “honorary” status within our CHS Class of ’90 – Jill Hennessy Shea.

Jill had actually moved away during our junior year due to a parent’s job move, and so she had not graduated with us. But she was one of those people who was so universally respected, well-liked, and valued all those years ago in high school, that we in our class just always laid claim to her as one of “ours.”

“You’re so sweet to think of me…!” Jill texted me back on August 10, 2025.

She said she hoped to make it to the event. I was excited about the prospect of seeing her. The last time I had seen Jill was at our last “big” reunion at our 20-year, back in 2010. I even have a picture of it. By pure chance, a photographer at the event had snapped a candid of me welcoming Jill, at the entrance of our old high school cafeteria, with a big hug…

For me, this picture captures so well my affection for Jill.

Our September 2025 reunion came and went, but sadly, I saw that Jill was among many unable to attend. I didn’t think too much of it, though. After all, we in the “sandwich” generation all know that life easily gets in the way of things.

Jill sent a very sweet note to our class on our Facebook group page, after we posted photos from the event. I also knew I’d hear from Jill during the upcoming holidays, as was usual, since she and I had been exchanging family Christmas cards for nearly two decades (I always loved watching her family grow and reading her updates from the past year).

But then, the unthinkable. Friday, October 31.

I abruptly caught sight during a random scroll mid-day on my Facebook feed a shocking announcement by Jill’s family: Jill had passed away on October 26. I was stunned.

A beautifully written obituary – which I read word for word, more than once – was attached to the family’s Facebook announcement. It mentioned that Jill had gone through “a brief but courageous battle with cancer.” My heart simply sank like a rock.

What she must have been going through in these very recent months… yet she had found time to text me back, and with such an upbeat tone and happy, encouraging words.

She was courageous, indeed.

I immediately relayed the news on to our high school Facebook page, and, as to be expected, the outpouring of sadness was immediate and heartfelt by all.

Speaking for myself, these past days have been so sad and even surreal, needless to say. My heart goes out to Jill’s beautiful family. The pain of the Hennessy and Shea family’s loss is, without question, unspeakable. I’ve kept going back to the lovely written tribute that was posted online… and with so much amazement at all that Jill accomplished in her life, both personally and professionally. It filled me with admiration and awe for Jill.

In re-reading it, there’s one thing that struck me in particular: Jill’s life of non-stop contributions to others – entirely consistent with the person we all knew her to be in high school.

I well recalled Jill’s academic achievements and her keen acumen in every subject, back in our school days. As it happened later, throughout life, Jill turned her substantial intellectual talents into an even more substantial career, on top of her roles as wife, mother, and community volunteer.

For me, absorbing this tragic news has taken my memories back, nearly four decades.

One aspect of my nostalgia is that it’s a Tennessee autumn right now. Each time I stepped outside this past weekend – feeling the Oct / Nov chill, smelling a touch of woodsmoke in the air, and seeing those Tennessee maples at peak color – it took me back to those Maury County autumns in 1987, ’88, ’89… almost like a soundtrack can do.

I still hold some of my most enduring high school memories with Jill during those fall season CHS pep rallies and football games, the Halloween Hayride we would host out at my parents’ farm, the Sub-Deb high school sorority events, the slumber parties… all of it that Jill and I were a part of, together with so many sweet friends.

So many memories of being young in our Middle Tennessee town, our futures still far out ahead of us, and enjoying the company of such wonderful people as Jill. My youngest daughter is now the age Jill and I and our friends were then, in these photos. It feels strange.

When I began thumbing through my old high school photo albums this evening, I marveled at how many photos I had of young Jill… but, of course I did!  She and I were so often in the same group, doing so many of the same things.

It makes me nostalgic but also glad to be able to share some of these pictures, particularly for classmates who remember those days, too, and how much Jill was part of that fabric of our youth. And, for those in Jill’s family, who can see just how much Jill was embraced by her friends back in her Columbia, Tennessee, days, just as she undoubtedly was beloved by everyone in what came to be her modern life.

Speaking from my memories circa 1987-89, we all simply loved being around Jill.

She was the kind of girl who consistently placed people at ease… never spoke a cross or unkind word, always treated everyone with the same respect, and truly cared about others in such an inquiring, authentic way. If something got you down and Jill perhaps caught sight of a sad look on your face in the school cafeteria or in the CHS hallway between classes, she would be quick to reach out and make sure you were alright. Her maturity belied her years.

You could trust Jill – in all things.

She exhibited a constant level-headedness that positively influenced others. At the same time, Jill was not the judgmental type, either… and frankly, that meant something in a small town. Her mode was very much “live and let live,” but at the same time, she modeled such a high standard in word and deed, that her positive ways came through to the rest of us, with even more compelling and influential effect.

These memories mean so much to me. Always have. Always will – but even more so, now.

I’m deeply thankful I had that little text exchange with Jill a few months ago. It was brief, but it reflected the mutual care of long-ago friends. I’m also very glad we had that class reunion a few months ago. Even though Jill couldn’t attend, I would not have had that last set of text exchanges with her, if we had not had the reason of the reunion to get back in touch before the holidays. Sometimes, it’s these little things that can mean everything.

It reminds me so much of how God blesses our lives with people, in ways and at times that can be under-appreciated until, suddenly, one day, it’s not. You see and appreciate and value everything they were to you, in its totality… even if a great deal of it lives as a collective memory, long ago. And you see what the world has lost in our having lost them… but what heaven has certainly gained.

Sending my love up there to you, Jill. How grateful I am that I knew you.