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Welcome to Coffee with Kevin – Weekly Reflection

Saturday mornings hit differently. The pace slows down, the coffee stays hot a little longer, and there is finally time to reflect instead of just keeping up with the week.

Welcome to Coffee with Kevin—my weekly space to step away from news headlines, charts, and rankings to share personal stories, practical lessons, and observations.

Some weeks, we’ll explore life in retirement, living in Brazil, photography, books, or family. Other weeks, I’ll draw on four decades in technology, leadership, and change management—offering perspectives that remain relevant long after leaving the office.

Think of this as two friends catching up over a fresh cup of coffee: honest conversation, stories worth sharing, and an idea or two to take with you into your weekend.

Grab your cup, settle in, and let’s dive into this week’s conversation:[Memories – The Last Time]

The Last Time We Never Knew Was the Last Time

I was sitting here the other day thinking about my past, and I started to wonder: Would I think about certain moments differently if I had known they were going to be the last time I would ever do them?

I drifted back to being a kid. All of my friends in the neighborhood got together almost every day to play whatever sport was in season. In the summer, we would gather in Scott’s yard for baseball or Wiffle ball. Fall meant football, and winter meant street hockey.

We did it so often that we never thought about it. Why would we? Tomorrow was always there.

But somewhere along the way, as we got older, there was a day when we walked out of Scott’s yard, or off that street, put our stuff away, and never gathered together like that again.

There was no announcement. Nobody said, “Well, boys, this is it. Thanks for the memories.”

We just went home.

And somehow, that was the end.

It is a little sad when you think about it. We spend so much of our lives doing things for what seems like the first time, or the hundredth time, rarely realizing that one of those ordinary moments will quietly become the last.

I look back at high school, and for some reason I remember exactly what my last day was like. I walked out the side door after midterms and just kept going. It was a cold day, and I had all my credits, so I was finished with high school halfway through the year.

I didn’t know it was a moment I would remember decades later. I just walked out the door.

I remember walking out of work on my last day, too, heading into retirement. I stepped through the door, looked back, and that was it.

That one felt different. There was sadness, but also satisfaction. Forty-plus years of working had come down to one final walk through a door. There was no dramatic music playing in the background, unfortunately. I didn’t even get a commemorative plaque.

I just went home.

But the one that stays with me the most is August 12, 2014.

I remember pulling out of the driveway, headed for Florida. My dad was standing there waving goodbye.

I had no idea I was seeing him for the last time.

That hurts even today.

Life moved quickly. By the time I was planning a trip back to see him, I think nearly three years had passed. Then he died.

My last vision of my father is still that driveway, that moment, and him waving goodbye.

There is a Brazilian Portuguese word, saudade, that is often translated as longing or missing someone. But it feels deeper than simply saying, “I miss him.” It is the strange ache of longing for someone who is no longer there, mixed with the memories of when they were.

I think that is what I feel when I remember that driveway.

Saudade.

And then there is hockey.

I played hockey most of my life. I even coached kids for a while. I spent countless hours on the ice, tying skates, taking them off, getting bruised, getting cold, getting yelled at by referees who were clearly wrong, and occasionally wondering why I was still doing this to myself.

And yet, I never knew when I pulled off my skates for the last time that it really was the last time I would ever skate.

There was no final faceoff. No announcement over the loudspeaker.

I just took off my skates and went home.

I guess life is odd like that.

It moves so quickly that we don’t stop to consider that the people we see, the places we visit, and the things we do may already be approaching their final appearance in our lives.

The last time you sit around a table with someone.

The last time your kids need you to drive them somewhere.

The last time you play a sport you love.

The last time you walk through the door at work.

The last time you say goodbye to someone you love.

We rarely recognize those moments while they are happening.

Maybe that is part of what makes life both beautiful and painful. If we knew exactly when something would be the last time, we might hold on tighter, pay closer attention, or say the things we sometimes leave unsaid.

But perhaps there is another way to look at it.

Maybe the fact that we don’t know is what makes those ordinary moments so meaningful. We don’t have to know something is the last time for it to matter.

That afternoon playing Wiffle ball mattered.

That cold walk out of high school mattered.

That final walk out of work mattered.

Those years on the ice mattered.

And that driveway in 2014 mattered more than I knew.

We can’t go back and change the last time.

But maybe we can be a little more present for the next time.

Because someday, without knowing it, the next time may be the last time.