iiinova — where your digital self keeps evolving

Andrew Simmons @adlsimmons.bsky.social · 06/10/2026

I'm working on an article about teachers who bring guests into the classroom to serve as visiting experts, judges, audiences, and more. I'd love to chat with any public or private school educators who make this practice part of their pedagogy. Please feel free to message me here.

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Andrew Simmons @adlsimmons.bsky.social · 18/08/2026

With Saunders (and I’m focused on the early stuff I teach more than the newer works) the cruelty of his worlds feels almost quaint compared with the tech CEO worship unfiltered bigotry comfort with violence now mainstreamed. Students are not shocked. Sedaris I flat out dislike. That’s just me maybe.

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Andrew Simmons @adlsimmons.bsky.social · 18/08/2026

The gangs in “CWLIBD” are characterized as multi-racial, probably to emphasize the nihilism cutting across demographics. I’ve taught two stories from that collection and they’ve felt relevant to teens (triumph of selfish bullies, sacrifice of morals for gain). I agree the fastball feels flatter.

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Andrew Simmons @adlsimmons.bsky.social · 16/06/2026

I often discuss with fellow alums the extent to which living in what was once “Internet House” and studying punchline postmodernists at Oberlin prepared me for spending middle age in this circus.

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Andrew Simmons @adlsimmons.bsky.social · 10/06/2026

Yesterday, I heard a sports podcaster disdainfully characterize him as "performative". It speaks to the current notion that all documented public acts = curated for image. Would it be less performative if, instead of sketching Hamlet, he prayed at a local church or did business meetings for a brand?

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Andrew Simmons @adlsimmons.bsky.social · 30/05/2026

My eloquent students are featured in a NYT video this morning. Justin, Daniella, and Cherise are heroes of Lit 12 and Journalism. They have magnificent aurae and participate in class discussions without trying to intellectually mog anyone. Young people to watch, for sure.

nytimes.com

Video: Can California Convince Teens to Work in Construction?

Facing an uncertain job market and the looming threat of A.I., graduating high school seniors in America’s tech capital are increasingly rethinking their career plans. Job demand in fields like constr...

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Andrew Simmons @adlsimmons.bsky.social · 07/05/2026

My mom worked at the Louisville newspaper and when Clinton stopped by on the trail he knew the name of everyone in the room—a big room—and did the eye thing. I remember hearing that (specifically about my mom’s colleague being essentially hypnotized) when I was in middle school.

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Andrew Simmons @adlsimmons.bsky.social · 02/05/2026

For volume 50 of my under-optimized newsletter on teaching in dark days, I write about how teen AI adoption hinges on loneliness and that a bot is the worst buddy a kid could have.

open.substack.com

50. More Human Than Human (Sycophantic, Overconfident, and Nosy)

A bot is a kid's worst friend...

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Andrew Simmons @adlsimmons.bsky.social · 01/05/2026

What if you’re two outta three?

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Andrew Simmons @adlsimmons.bsky.social · 01/05/2026

The Google one about the basketball kid asking a bot for a training regimen so he can hit “the big shot” is great too.

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Andrew Simmons @adlsimmons.bsky.social · 09/04/2026

Good to have yet another reason not to buy that coffee. Didn’t even like the vibe back in the day on 24th street.

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Andrew Simmons @adlsimmons.bsky.social · 25/03/2026

It's infuriating considering how many likely endeavor to get a piece of writing into this series. The prose in that piece is not particularly good but its AI voice has to be modeled/optimized re: what NYT likes, so is it not basically NYT loving itself instead of trying to find exciting voices?

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Andrew Simmons @adlsimmons.bsky.social · 23/03/2026

For profit-averse newsletter #49, my sloppy conversation-with-myself about teaching English in grim times, I discuss my favorite 2025 film The Secret Agent and the idea of modeling "small-h heroism" in class.

open.substack.com

49. Let’s All Go to the Lobby

History, small-h heroism, memory, The Secret Agent, Judy Hopps, a box of Whoppers, and a keg-sized soda cup filled with ice and everything carbonated…

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Andrew Simmons @adlsimmons.bsky.social · 23/03/2026

Just had a training on this stuff and that’s what I said!

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Andrew Simmons @adlsimmons.bsky.social · 22/03/2026

In cadence and tone, it's a ringer for what my HS students submit when they are trying to pass off a Gemini production as their own fiction or personal narrative.

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Andrew Simmons @adlsimmons.bsky.social · 11/03/2026

Speaking of which, I'm reporting an article for publication about how HS teachers are handling the instruction of writing conventions in English classes in the current era. Any teachers in the building should feel free to send a chat my way if interested in sharing thoughts...

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Andrew Simmons @adlsimmons.bsky.social · 11/03/2026

Grammarly is also the most noxious AI plagiarism tool for HS students. A Trojan horse of false legitimacy dedicated to getting them insecure about their ideas and abilities AND dependent on generative AI "inspiration" and prose glow-ups. Hate, hate, hate!

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Andrew Simmons @adlsimmons.bsky.social · 05/03/2026

Hello! I am reporting an article for a national publication about the challenge and value of teaching writing conventions and proofreading. I’d like to interview high school English teachers at both public and private institutions! Shoot me a message if you're interested.

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Andrew Simmons @adlsimmons.bsky.social · 04/03/2026

With the same voice, through history? Or was it time? Cannot recall!

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Andrew Simmons @adlsimmons.bsky.social · 21/02/2026

I like to add “like a DOG!” To pretty much anything unrelated to killing.

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Andrew Simmons @adlsimmons.bsky.social · 19/02/2026

Agree. My knees, ankles, and hips don’t like it but I have had the same experience everywhere I’ve taught. I’m a good player so it helps build respect both ways but it’s also sports as a show of care and a willingness to risk failure publicly (which is school for many kids).

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Andrew Simmons @adlsimmons.bsky.social · 14/02/2026

Been doing this with my students (earnestly, candidly) for years.

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Andrew Simmons @adlsimmons.bsky.social · 11/02/2026

Last week, I wrote for @edutopia.org about teachers coping with too many software licenses for products that feel inconsistently useful, weaving my own experiences into a reported piece.

edutopia.org

Have Teachers Reached App Overload?

Educators are overwhelmed by an avalanche of tools. The solution isn’t zero tech, but the question of balance is critical.

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Andrew Simmons @adlsimmons.bsky.social · 06/02/2026

Curious how many district-level positions are being cut...

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Andrew Simmons @adlsimmons.bsky.social · 06/02/2026

Five years ago, I wrote about several students adding the image of an ape to a presentation about Black history (related to a unit on Kindred). The kids characterized it as a subversive "joke" and claimed, ironically, given the context, not to get why it was perceived as racist.

andrewsimmons.substack.com

6. Race to the Top

Updating the flow chart...

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Andrew Simmons @adlsimmons.bsky.social · 26/01/2026

In #48 of my newsletter about teaching high school in a depraved newsletter, with reflection on Minnesota and a trip down memory lane, I consider the allure of apathy for teens and express some optimism. Solidarity is the only path for the grievously disaffected!

open.substack.com

48. You Can Get With This, or You Can Get With That

The weekend crystallizes for teens a binary choice: bridge distance and take up the mantle of all-American solidarity or join the goons…

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Andrew Simmons @adlsimmons.bsky.social · 26/01/2026

A short story about a NYT mag story profiling a therapist who coaches AI bots in the 2030s through a reckoning with the tough times they experienced in their mid-2020s childhood is just there, waiting to be written..

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Andrew Simmons @adlsimmons.bsky.social · 17/01/2026

I used #47 of my poorly optimized newsletter to reflect on a country trying to edit itself and its history as my students edit their writing and selves. From Minneapolis to national parks to 1984 to the writing process…

open.substack.com

47. Processin'

Revising the country, its history, one's self, and an essay...

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Andrew Simmons @adlsimmons.bsky.social · 06/01/2026

Also studying American cinema and postmodernism. We’ve got quite a text here.

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Andrew Simmons @adlsimmons.bsky.social · 16/12/2025

One interesting bit is the usage of Grammarly to simply “clean up” writing. Grammarly has a generative AI feature that changes entire documents with a click: “make it confident,” “make it persuasive,” etc. Students can use this and feel authentic unlike when they put prompts into chat gpt…

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Andrew Simmons @adlsimmons.bsky.social · 08/12/2025

For #46 of my boutique newsletter dedicated to teaching English to teens in dark times, I share a medication-scrambled thought-vomit from Thanksgiving vacation: the next book for educators I just might write.

open.substack.com

46. From Kyoto, On Drugs: A Maybe-Book Stirs

How any class can make better communicators, planners, problem-solvers, and community members through journalism…

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Andrew Simmons @adlsimmons.bsky.social · 08/12/2025

I had that reaction to the joint-in-mouth selfie on the couch as his kid goes off to fight fascism. Too perfect.

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Andrew Simmons @adlsimmons.bsky.social · 28/11/2025

Both red fern and bridge in fourth grade for this guy. Along with “a taste of blackberries.” And Roots, the whole TV series! In class!

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Andrew Simmons @adlsimmons.bsky.social · 03/11/2025

They pretend that sentiment does not exist but view every slightly wishy-washy likely-R voter as this unlearned kingmaker to be soothed like a fussy baby.

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Andrew Simmons @adlsimmons.bsky.social · 21/10/2025

Watching this was fascinating after having Wigand for high school chemistry.

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Andrew Simmons @adlsimmons.bsky.social · 13/10/2025

A very bad recent diagnosis, a sudden authentic spiritual awakening, and/or a decision to pack everything/everyone along for the trip…

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Andrew Simmons @adlsimmons.bsky.social · 06/10/2025

I’ve found that high school students (I teach) often don’t even perceive AI use in brainstorming/writing process as inauthentic, because the app extension is in the document advising them, because they see it as an extension of the self.

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Andrew Simmons @adlsimmons.bsky.social · 05/10/2025

When this man writes, I just hear the porter from Macbeth hissing “equivocator” over and over.

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Andrew Simmons @adlsimmons.bsky.social · 04/10/2025

Also: an elderly man pushing a wheelchair on a quiet tree-shrouded street with evidence of bike use and public transit. What is that code for?

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Andrew Simmons @adlsimmons.bsky.social · 04/10/2025

Seems like it’s time for the 82nd Airborne to come deal with farm-to-table cuisine and the inevitable products of drug wars and public health failures.

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Andrew Simmons @adlsimmons.bsky.social · 26/09/2025

Nothing is more fun (as a journalist) than (as a teacher) getting to speak with bright, reflective, serious educators about their work. I find journalistic curiosity and teaching practice satiated, two birds, one stone, and so forth.

edutopia.org

Tackling the Question of Character Development in the Classroom

Using texts, projects, and classroom policies, some English teachers encourage self-reflection and teach social responsibility.

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Andrew Simmons @adlsimmons.bsky.social · 17/09/2025

The Articles must be protected at all costs. We have to write and share them. Together. On the same page. America is made up of many Articles. Some I like, some I don’t. But I’ll defend your right to Article to the death. Our Articles sit together in the pews of the Times. Along with our Pods.

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Andrew Simmons @adlsimmons.bsky.social · 12/09/2025

In addition to providing therapy and companionship!

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Andrew Simmons @adlsimmons.bsky.social · 12/09/2025

My sense, as a teacher and observer, is that a lot of young people are simultaneously lonely/sad, fairly privileged, desensitized to depictions of suffering, perma-distracted, and very very bored. "Recreational nihilism" is accurate and may in fact appear in my upcoming unit on The Stranger....

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