They say you can learn a lot by asking questions. You can also learn a lot by listening.
Last month, I made plans to spend a long weekend in Florida with my dad since he wasn’t planning on coming up for the holidays. Between the time I booked the trip and the moment wheels were up on my flight south, his real estate agent called with news: there was a serious offer on his apartment.
For context, Dad moved to assisted living back in March after a roller coaster of health scares. The closing was scheduled for the exact weekend I was coming down, so to say the stars aligned would be an understatement. He’s 93. There was a lot of confusing paperwork and no shortage of jobs-to-be-done to get the apartment sale ready. Not only would there be a financial benefit due to the sale, dad’s not having to pay taxes, assessments, common fees, and that pesky monthly charge at the pool restaurant was a tremendous weight off his shoulders. Christmas came early indeed!
My brother Jimmy—acting in his official role as Chief Legal Officer of the family—booked a last-minute ticket (in the right order, I might add) and joined us. On Friday night, we took Dad to his club, which always does a great job with holiday decorations, and we had a genuinely great time. Jimmy flew home Saturday morning, leaving me with one more full day.
That day was simple in the best way. I helped Dad by running a few errands, went with him to the five o’clock Mass at Our Lady of the Elderly (just kidding, the Mass was at the auditorium at his facility – John Knox Village), and then we had an early dinner. Afterward, we went back to his room and just talked for a while. Neither of us was interested in TV—though I’ll admit I was itching to watch a Hallmark movie, I didn’t feel like subjecting him to that.
Somewhere in that conversation, under the learn something new every day category, I found out that my grandfather—who I never met because he died a few months before Jimmy and I were born—only had a sixth-grade education.
I had to let that sink in. His son, my father, went on to have a tremendous career as an executive at American Express and built a wonderful life for my mother and siblings. That life came from a one-income household led by a man who never made it to middle school.
My grandfather started out as a milkman. I learned that my grandmother’s mother—my great-grandmother—told him that if he wanted to marry her daughter, he’d need a better career than delivering milk. So he became a cop.
My father remembers him going to “cop school” at night to earn his high school diploma, which opened the door to promotions within the New Rochelle Police Department. Over time, my grandfather rose
to the rank of Lieutenant and received multiple commendations for his work.
And then there was my grandmother.
I learned just how instrumental she was to this family’s success. She could stretch a dollar like you wouldn’t believe. Growing up, my father often said I should have attended the Grandma Carlon School of Economics as saving money from my taxing lifeguarding job wasn’t a strong habit. Grandma took what little money my grandfather earned and somehow made sure the family—including two very tall boys—never went hungry.
Looking back, I realize how much I took my own upbringing for granted. My father was older when I was born and more established in his career. We didn’t take fancy vacations, but we always made it to Florida in the winter—often by car. There was always an overabundance of food on the table because my mother “cooked enough for the Russian army,” according to Dad. I never had to take out a student loan. There was always a car when I needed one. Life for my siblings and me was, for the most part, comfortable.
Dad’s wasn’t. He worked a number of jobs to get himself through high school and college. He scooped ice cream at Schoppe’s in New Rochelle and would bring some home for my grandmother, who ate it late at night while waiting for my grandfather to finish his beat. He drove a bus. He delivered mail—learning where all the “gin joints” were in town along the way. He served in the Coast Guard. Eventually, he became a salesperson at American Express.
I’ll say it plainly: we had it easier. I can’t help but wonder, though, if he would be where he is today had life been easier for him. He shared that when he retired, he and my mom didn’t take any big, splashy trips. Most of their travel happened while he was still working—often on Amex’s dime after winning sales excellence contests. In retirement, they played golf at their club, socialized with friends, and bounced between Connecticut and Florida, frequently driving just like we did when we were kids. He saved his money, and invested it wisely in an ocean front condo which no longer bears his name.
Sitting there with him, I realized how little of this I would have known had I not slowed down long enough to listen. Not ask, just listen.
There’s something about the holidays that invites nostalgia, but this felt different. This wasn’t about longing for the past. It was about understanding the scaffolding that held it all up. About seeing my father not just as my dad, but as a man shaped by sacrifice, discipline, and a quiet kind of ambition that never needed applause.
It’s humbling to trace a line from a sixth-grade-educated milkman who went to cop school at night, to a lieutenant with commendations, to a son who built a remarkable career, to a family that—without fully realizing it—benefited from every late night, every second job, every mile driven instead of flown. None of it accidental. None of it easy.
I don’t think my father succeeded despite those challenges. I think he became who he is because of them.
As the holidays approach, that’s one lesson I’m carrying with me. Gratitude isn’t just about being thankful for what we have. It’s about understanding where it came from. About recognizing that our comfort often rests on sacrifices we never had to make ourselves. About honoring the people who quietly did the work so we wouldn’t have to.
This year, when we gather around tables heavy with food, complain about long drives, or worry about things that—if we’re honest—aren’t all that heavy at all, I’ll think back to that night. That room. A father sharing stories. A son listening.
And I’ll say thank you—not just with words, but with attention. Because sometimes the greatest gift we can give the people who raised us isn’t another thing. It’s our time. And our willingness to truly uncork their story.
