The Glorious Blahs of November

by | Nov 26, 2025 | Blog

Dear Friends of Boundless,

We earned three Top-Impact Charity Awards this year, nationally and for Toronto, from Charity Intelligence. These awards brought many of you to our doorstep, and that’s a big deal. Your support sponsors countless stories like the one below.

I returned to the Boundless world yesterday after a painfully long stint in Toronto and got the chance to run an evening program — an event this community refers to, affectionately and somewhat cynically, as a “Stevening.”

The topic: “You Don’t Know Shit – Part One.”
Part Two, coming next week, will be titled, “It’s Shocking What You Know.”

The evening started well. The kids locked onto the theme instantly and began their finger-wagging early. We explored how organizations “don’t know shit,” and it was fun to lambast humanity with the benefit of hindsight. Morality and virtue are crystal clear for teenagers, don’t ya know.

Then we shifted into trickier terrain: What about our own baggage? Can we admit we don’t know shit about ourselves?

Using an ancient Star Trek episode to show how the versions of ourselves can stay hidden, the stories started flowing like the Madawaska River out back. (Pseudonyms used below.)

Sean described a moment of rage toward his sister when a realization hit him like lightning,

“In that moment, I knew I had become my mother.”

Sammy spoke about a parent’s alcoholism.

“I could be next,” he said quietly.

Not all the realizations were dark. Kentucky confessed her shock at being an extravert.

“When things went south, I just stayed inside. I never knew I liked people so much.” Then she added: “If they’re the right people.”

The evening ran past the allotted time, and later I hung out with a cluster of these precious and precarious younglings. One conversation still lingers.

Dylan, who’s given me permission to use his real name, was carrying himself with a confidence I’d never seen before. So much so that he started going at me,

“Steve, why didn’t you bring up Krispy Kremes for Evan’s birthday like you did last year?”
“You still haven’t gotten back to us on the environmental audit!”
“And why not build a roof over the hockey rink?”

All this from a young man who recently discovered fitness. My theory? This is the root of his emerging swagger. He must have dropped twenty pounds and his pipes are getting scary.

November, in our tiny Boundless bubble, is considered the hardest month of the boarding school. It’s dreary. Dank. The Wreck of the Edmund Fitzgerald month.

It’s also overloaded with compulsory subjects like Math and English, academically the toughest stretch of the year by far.

And yet, despite the rain pounding outside as I write, this November is kind of fabulous. The kids are hanging in. They like each other and are bonded tight. And we will try to officially retire those ridiculous little cream cups and get our environmental act together.

Thanks for making all this happen, dear friends.

Warmly,

Steven

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Steven Gottlieb
Steven Gottlieb