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Choose Your Hard: Why We Can’t Let AI Do the Thinking #63
I’m breaking my “Monday-only” rule to bring you this special conversation.
I’m currently out in the yard taking advantage of spring break—dealing with the real-world friction of some landscaping—but this interview with Michael Wish felt like the perfect bridge for what we’ve been discussing this week.
Michael and I both grew up as “Air Force brats,” and we ended up in a deep dive on what it actually means to master a craft. We talk about the “AI Glaze”—that polished, robotic output that makes students feel like they’ve finished the work when they haven’t even started the learning.
If you are a teacher or a parent wondering how we protect our kids’ ability to think in a world of “easy buttons,” this episode is for you.
In this episode, we discuss:
* The 40-Year Perspective: Why I’m still a teacher in the trenches and why I’m more excited about the classroom now than I was in 1986.
* Melting the AI Glaze: How the Mastery Flip reclaims the classroom for human connection and Socratic defenses.
* The 10-Hour Release Pin: Why the “messy middle” of a project is where the actual character is built.
* Choose Your Hard: The lesson my father learned flying F-4 Phantoms in Vietnam—it’s hard to do the work, but it’s harder to live with the consequences of not doing it.
Key Moments
* [00:00] Intro from the Yard: Landscaping on spring break and choosing your “hard”.
* [01:05] The 40-Year Journey: Starting in 1986 in Denver to becoming a pioneer of the flipped classroom.
* [03:01] The Pull Back to the Classroom: Why Jon returned to teaching in 2019 after 7 years on the road.
* [07:29] The Primary Role of a Teacher: Why inspiration and passion matter more than just explaining.
* [11:03] Origins of the Flipped Classroom: How a rural school in Colorado and missed classes started a movement.
* [19:01] The Mastery Viva: Protecting cognition through high-impact Socratic conversations.
* [22:20] The AI Forklift: Why using AI improperly is like taking a forklift to the weight room.
* [24:54] Skylow & Interactive Video: Using AI avatars to build engagement in the independent space.
* [27:33] The Trebuchet Project: A case study in cumulative mastery and authentic assessment.
* [31:10] The Fighter Pilot Legacy: Lessons in “Choosing Your Hard” from an F-4 Phantom cockpit in Vietnam.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonbergmann.substack.com
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By Jon
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22 ratings
I’m breaking my “Monday-only” rule to bring you this special conversation.
I’m currently out in the yard taking advantage of spring break—dealing with the real-world friction of some landscaping—but this interview with Michael Wish felt like the perfect bridge for what we’ve been discussing this week.
Michael and I both grew up as “Air Force brats,” and we ended up in a deep dive on what it actually means to master a craft. We talk about the “AI Glaze”—that polished, robotic output that makes students feel like they’ve finished the work when they haven’t even started the learning.
If you are a teacher or a parent wondering how we protect our kids’ ability to think in a world of “easy buttons,” this episode is for you.
In this episode, we discuss:
* The 40-Year Perspective: Why I’m still a teacher in the trenches and why I’m more excited about the classroom now than I was in 1986.
* Melting the AI Glaze: How the Mastery Flip reclaims the classroom for human connection and Socratic defenses.
* The 10-Hour Release Pin: Why the “messy middle” of a project is where the actual character is built.
* Choose Your Hard: The lesson my father learned flying F-4 Phantoms in Vietnam—it’s hard to do the work, but it’s harder to live with the consequences of not doing it.
Key Moments
* [00:00] Intro from the Yard: Landscaping on spring break and choosing your “hard”.
* [01:05] The 40-Year Journey: Starting in 1986 in Denver to becoming a pioneer of the flipped classroom.
* [03:01] The Pull Back to the Classroom: Why Jon returned to teaching in 2019 after 7 years on the road.
* [07:29] The Primary Role of a Teacher: Why inspiration and passion matter more than just explaining.
* [11:03] Origins of the Flipped Classroom: How a rural school in Colorado and missed classes started a movement.
* [19:01] The Mastery Viva: Protecting cognition through high-impact Socratic conversations.
* [22:20] The AI Forklift: Why using AI improperly is like taking a forklift to the weight room.
* [24:54] Skylow & Interactive Video: Using AI avatars to build engagement in the independent space.
* [27:33] The Trebuchet Project: A case study in cumulative mastery and authentic assessment.
* [31:10] The Fighter Pilot Legacy: Lessons in “Choosing Your Hard” from an F-4 Phantom cockpit in Vietnam.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonbergmann.substack.com