Writing Boots

On communication, professional and otherwise.

My overwhelming Embarrassment of Riches

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I grew up in a quiet house. Shy writer parents, in a small Ohio town. I was my dad’s best friend. My little sister was my mother’s. If the phone rang, my dad bellowed, “Who could that be?” And if the doorbell rang! My sister and I knew it had better not be one of our friends (of whom we only had small handful of each, ourselves).

My life—in Chicago and through my work, around the world—became an existence no more fathomable or manageable to my parents than Frank Sinatra’s or Taylor Swift’s.

My parents, or me.

I don’t know how to handle this. How much longer can I keep this up before my brain/heart/soul/life explodes?

The answer is, the friends I choose, and who seem to choose me: usually, people who have a lot of their own people, and so they understand. In any case, they are so much more graceful about it than I am.

For instance, they don’t write shit like this, about how anxious they are about all the friends they have. Jesus!

But anyway, here’s what some of my people looked like last weekend in the Michigan woods. After a similar gathering last year, I called them, “a group of friends the loving, honest, soulful, funny likes of which even my own good fortune never began to prepare me to deal with.”

Never even began.

CAPTION: AI OIL-PAINTING TREATMENT BY EVENT ORGANIZER JOE RILEY, PICTURED IN BLACK T-SHIRT, TOP MIDDLE.

I’m My Own AI

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You’ve heard the song, “I’m My Own Grampa.”

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Well at this point, I’m my own AI. Or my own LLM, anyway. I call it Boots GPT. And it works automatically.

After almost 5,000 posts here—all of them on or around the subject of human communication—a thing will happen in the news or in my family or in my mind.

I’ll begin writing something about it. Halfway through the lead, I’ll get this feeling: Haven’t I written something like this before? I’ll query the Writing Boots search box for a keyword. Inevitably, up will come a post I wrote on the subject from 2018. Or 2013. Or 2009. (Or increasingly, troublingly, 2025.)

So more often than not, I repost the old one, with a little introductory note reestablishing the context. (And acknowledging that the piece is yesterday’s thought.) That may look lazy to you. (And so I’ve heard from some of you.) But writing a well-crafted old piece anew seems crazy to me.

The more important question is, why do I keep writing the same things over and over, like boats against the current, borne back ceaselessly into the archives? Familiar stimulus sparks repeat reactions. “We’re wet machines,” my writer buddy Mike Long always says. “Just wet machines.”