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The columnist and his son outside the place the Grateful Dead played at Cornell University. (Free Press file photo)

COLUMN: ‘A Pirate Looks at 50’

by | Jun 22, 2026 | ALLFFP, Columns, Region

I stole that headline.

It’s the title of a book by Jimmy Buffett. And though I’m more of a Dead Head, a fan of the Grateful Dead, than a Parrot Head, a Buffett aficionado, I liked the man, and the words fit.

That’s because I turned 50 on Friday. It hasn’t felt that much different than 49 over the past few days — but it seems like it should be different.

Actually, I’ve felt the same for years. Sometimes, physically, I feel super old. It really is true that as you age, you experience random pains. I’ll just be sitting in front of the TV, for example, not using my feet, and then a foot will hurt.

Conversely, sometimes, socially, I feel about 16. To quote another song, Vance Joy’s “Riptide,” I can be “scared of pretty girls and starting conversations.”

But it’s just sometimes. The rest of the time, a lifelong career in news reporting has prepared me to ask anyone anything at any time.

So maybe the meaning I’m looking for isn’t about how you feel.

It could be about this: Maybe, at any age, one should consider whether the life was well lived.

That “pirate” headline relates to how I feel as a journalist. I started writing news stories in the mid-1990s, and almost as soon as I began, people would suggest that newspapers were becoming obsolete.

Then, after I left daily journalism to stay home with my son when he was a baby, there was a question of whether I would ever get another news job, so many of them having been cut all over the country.

The third strike was when I was really sick right before the pandemic, with a combination of OCD — I really have it; I don’t just like things neat, as some people characterize the illness — and what I now think was PTSD.

Really, I didn’t know if I’d ever be able to write again.

Somehow, though, I have found a way to bring these words to you, the reader, after each setback.

That’s because I didn’t worry about other peoples’ rules, kind of like a pirate.

Or, perhaps more accurately, like a cowboy. After maybe about age 16, I started thinking of cowboys not as people literally involved in agriculture, or as the white hat-wearing heroes of westerns, but as guys who thought the rules didn’t apply to them. And by this, I meant “cowboy” as a negative.

Now, however, I think of myself as a cowboy because I made my own way. I’m still here pounding away at the laptop, even though two of the papers I worked for don’t exist anymore and many of the others are struggling.

So that’s kind of how I think of myself, despite the fact that I look silly in a cowboy hat and would like even worse with cowboy boots.

But what else of reaching a milestone age?

The other day, I sort of decided a life well lived is judged by whether you end up with more friends or more enemies. On this, so far, I’ve won.

Oh, I have enemies. They’re the handful of folks I haven’t been able to forgive, despite a lifetime of listening to Christian teaching.

One idea I had for today’s column was to identify these terrible figures and describe how I had gotten one over on them.

But that’s not what this forum is about. Even though I think you might have laughed at some of that score-settling.

When I thought about that, I came to this instead: In spite of what I say about being a curmudgeonly old reporter who doesn’t like a lot of people, that’s not true. I have an army of friends.

The best thing about social media, in my opinion, is when your birthdate comes and you see all of the varied people, from all different parts of your life, who wish you a happy birthday. It really is amazing.

I have good friends, too. The kind who would do anything for you.

I’m reminded of the joke that a friend is “someone whom you ask to help you move,” but a real friend is “someone whom you ask to help you move a body.”

But my editors might not let me KEEP writing this column if go much further down that line of thinking.

So let’s agree to end on something more positive. The main thing I fear in life isn’t spiders, snakes or anything like that, though I’d move if I ever lived in a house that had a rodent problem.

I mainly fear failure.

That’s why I cried — but just one tear, mind you; remember, I’m a cowboy — the first time I saw this message at the end of one of my favorite films, “It’s a Wonderful Life:”

“Remember, no man is a failure who has friends.”

Well, OK, as I had to admit to an old friend once, maybe I’ve cried at that part of the movie more than just that first time …

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