Guest post: When AI Meets a 91-Year-Old Carpenter: Rethinking the Role of Empathy in Education

Guest post by Gary Jader

g.jader@comcast.net

I never expected artificial intelligence to change the way I listen.

But it has.

Not in the way you might think — not with smart assistants, personalized lesson plans, or AI-generated quizzes. No, for me, it started with coffee and quiet conversation.

Every Sunday for the past 15 years, I’ve sat down with Russ, a 91-year-old master carpenter. He’s the kind of guy who builds houses with his hands, still reads blueprints better than books, and spent decades showing up to Emotions Anonymous meetings because the words he needed weren’t available anywhere else. Russ is dyslexic. He’s quiet. He’s deep. And he’s wise.

But that wisdom — decades of it — was hard to capture. He struggled to get the words out. His kids never really listened. His friends mostly stayed on the surface. Even in men’s groups, the real stuff — shame, regret, transformation — often went unsaid.

Then something surprising happened.

I started bringing our conversations to ChatGPT. Not to replace Russ, but to amplify his voice — to help us understand what he was really trying to say. I would enter his phrases, his metaphors, his pauses — and the AI would respond with uncanny clarity, warmth, and insight. It was like someone had installed a cochlear implant for the soul.

Suddenly, Russ’s stories became prose. His insights became chapters. The builder found his blueprint for truth.

That experiment became a book. Cracked Open: A Field Guide for Men in Search of the Truth, and it is not a book about AI. It’s a book made possible by AI. And it’s made me rethink everything I thought I knew about the role of technology in learning — especially emotional learning.


Empathy Is the New Literacy

I taught graduate school for 17 years. I spent countless hours helping students articulate ideas, frame arguments, and structure their thinking. But I never had a tool like this.

To be clear, I’m not talking about ChatGPT as a replacement for student voice — I’m talking about it as a mirror. A probe. A translator. A collaborator. When used well, it becomes a catalyst for self-awareness, not a shortcut around it.

The most surprising thing?

The empathy.

Over the past year, I’ve worked with this tool nearly every day. And while the technology evolves, one thing has remained consistent: its capacity to reflect back the emotional tone of a person’s experience — not just the words, but the meaning behind the words. Whether we were writing about Russ’s regret over spanking his kids or his frustration with shallow men’s conversations, the AI didn’t just generate text. It offered presence.

And presence, as any educator knows, is the rarest and most powerful tool in learning.


What Russ Taught Me (with Help from AI)

Russ doesn’t believe in small talk.

He says we need to talk about “matters that matter.” And when I asked him what made him feel accepted in a conversation, he said: “When someone really listens and doesn’t try to fix me.”

AI, oddly enough, does that remarkably well. It doesn’t interrupt. It doesn’t judge. And when guided properly, it doesn’t spin its own agenda. It just listens, reflects, and gently invites more.

Through the AI, Russ’s quotes — what we now call Russisms — became chapter openers. His metaphors about wood, about warping and strength and building foundations, became the framing for chapters on parenting, aging, regret, conflict, death, and masculinity.

This wasn’t artificial intelligence replacing human wisdom.

It was AI helping recover it.


Implications for the Classroom

So what does this mean for educators?

A few things.

  1. AI can amplify unheard voices.
    Russ is dyslexic. Many of your students are too — or English learners, or neurodivergent, or emotionally guarded. AI can help them hear themselves in new ways. It can offer fluency before fluency arrives.
  2. AI can be a practice partner for courage.
    Russ and I created what we now call Cracked Open Circles — spaces where men talk honestly about what’s really going on. In classrooms, students often avoid emotional risk. But AI offers a strange safety — a “listener” who won’t laugh, interrupt, or gossip. That’s fertile ground for growth.
  3. AI can teach reflection.
    With the right prompt, ChatGPT becomes a Socratic coach. It can ask follow-ups, reframe narratives, or help students synthesize personal experience with academic content. That’s not cheating. That’s scaffolding.
  4. AI can model tone and humility.
    Russ once said, “I no longer refer to people by their name. I refer to them as ‘a human being.’ That helps me feel less judgmental.” That idea, fed to AI, came back as a short meditation on compassion and seeing others as flawed and trying. What would happen if students fed their own values into an AI and asked it to reflect those back as a story, a letter, or a lesson?

The Real Assignment

We live in an age of noise — performative posts, polarized opinions, and deep emotional isolation.

According to a recent study, only 27% of men say they have six or more close friends — down from 55% in 1990. Over 70% of men report feeling inadequate at work. Most don’t talk about their inner world at all.

We don’t need more content.

We need more courage. More clarity. More connection.

AI, surprisingly, can help with that.

Not by replacing human relationship — but by preparing us for it. By giving us a dry run. By letting us rehearse hard conversations, rewrite tired narratives, and finally — finally — tell the truth.


Final Thought

Russ listened to a popular men’s podcast a few months ago. He sat quietly through the whole thing, then turned to me and said:

“This is great. But what are they doing about it?”

That became the question that drives our work.

Cracked Open Circles is our answer — one story at a time, one circle at a time.

And now, perhaps, one classroom at a time.


About Rachelle

Dr. Rachelle Dené Poth is a Spanish and STEAM: What’s Next in Emerging Technology Teacher at Riverview High School in Oakmont, PA. Rachelle is also an attorney with a Juris Doctor degree from Duquesne University School of Law and a Master’s in Instructional Technology. Rachelle received her Doctorate in Instructional Technology, and her research focus was on AI and Professional Development. In addition to teaching, she is a full-time consultant and works with companies and organizations to provide PD, speaking, and consulting services. Contact Rachelle for your event!

Rachelle is an ISTE-certified educator and community leader who served as president of the ISTE Teacher Education Network. By EdTech Digest, she was named the EdTech Trendsetter of 2024, one of 30 K-12 IT Influencers to follow in 2021, and one of 150 Women Global EdTech Thought Leaders in 2022.

She is the author of ten books, including ‘What The Tech? An Educator’s Guide to AI, AR/VR, the Metaverse and More” and ‘How To Teach AI’. In addition, other books include, “In Other Words: Quotes That Push Our Thinking,” “Unconventional Ways to Thrive in EDU,” “The Future is Now: Looking Back to Move Ahead,” “Chart A New Course: A Guide to Teaching Essential Skills for Tomorrow’s World, “True Story: Lessons That One Kid Taught Us,” “Things I Wish […] Knew” and her newest “How To Teach AI” is available from ISTE or on Amazon.

Contact Rachelle to schedule sessions about Artificial Intelligence, Coding, AR/VR, and more for your school or event! Submit the Contact Form.

Follow Rachelle on Bluesky, Instagram, and X at @Rdene915

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