Distributing the future unevenly, on purpose
The AI era requires ambidexterity, institutional and instructional. Here's what that looked like at my school this week.
I met Mike Taubman in early November at the Center on Reinventing Public Education’s Think Forward fellowship gathering, where we quickly discovered we share more than our CRPE fellowship status. Over several days of intensive discussion, our cohort wrestled with a fundamental tension that has emerged in education’s AI moment: do we adapt our existing structures to accommodate these new systems, or do we reimagine education entirely? The question split the room. Some advocated for careful, incremental integration within current frameworks, while others pushed for wholesale transformation. On the final day, a small group worked to find a path through this apparent impasse, landing on an insight that felt both pragmatic and profound: maybe we need both approaches simultaneously.
Perhaps, we realized, the first approach (thoughtful adaptation within existing structures) isn’t a rejection of transformation but rather an essential laboratory. By experimenting with AI integration in our current contexts, we gain the practical intelligence needed to inform more ambitious systemic reform. This isn’t compromise; it’s epistemological humility paired with strategic patience. We learn by doing, and what we learn in classrooms today shapes what we can build for tomorrow.
In this guest post, Mike explores how this dual approach manifests in his own classroom at North Star Academy, where he’s building what he calls “institutional and instructional ambidexterity.” Through the stories of students like David and Savannah, Mike shows us what it looks like to hold past and future in tension: maintaining rigorous traditional academics while simultaneously pioneering AI-integrated career exploration and purpose development. His work offers a concrete example of the kind of bridge-building we discussed at CRPE, connecting what’s enduring in education with what’s emerging. In the weeks ahead, I’ll be writing about how ambidexterity plays out in my own context, but for now, I’m grateful to share Mike’s vision of education as a carefully woven rope. Not a knot to untangle, but strong cords bound together to support students as they cross into their futures.
“The future is already here. It’s just not evenly distributed yet.”
— Attributed to William Gibson
David and Savannah
David is a 12th grader in my 4th period class every day. He’s currently exploring a career as a vet. In September, after a field trip to the largest medical school in our city, David was considering a nursing career. In October, to explore a career in graphic design, he created this year’s hoodies for our program. Today he used AI to get support with a project exploring the medical issues dogs face most commonly in different parts of their bodies and then running short simulations of how to address those issues.
David comes to my class after AP Research, African-American Literature, and Physics. After my class he goes to lunch, AP Statistics, gym, and College Seminar (a class to support students with the college application process). Twice a week he has a financial literacy class in which he develops a credit score over time as he moves through a simulated life complete with an apartment he has to buy furniture and pay rent for, a job he has to maintain, and possible stock investments he might want to make.
Savannah sits next to David in 4th period. She’s also a senior and has known she wants to be a Psychiatric-Mental Health Nurse Practitioner (PMHNP) since the first day of the year. Every month she’s done a new project related to the same field. This month she’s working on a set of cards to share around the school that explain basic mindfulness and breathing techniques to support students with the stress of high school. She got the idea partly from a conversation with a psychiatric nurse earlier this year.
Savannah comes to my class after Fabrication Lab (our school’s makerspace), Latin American Studies, and African-American Literature. In that last class, she reads and discusses authors like James Baldwin, Gloria Naylor, and bell hooks, and then every Friday engages in “Synthesis Seminars” when she and her classmates apply authors’ ideas to their lives. After my class she goes to lunch, AP Statistics, College Seminar, and gym. Twice a week she has Financial Literacy with David.
Tomorrow, David and Savannah will give each other feedback on their current projects. They’ve been supporting each other’s work all year, as David casts a wide net to explore future paths and Savannah digs deeply into the road she plans to take. Next week on Monday they’ll rehearse their project presentations together before sharing them formally with other students on Tuesday.
One Day, Many Epochs: Institutional Ambidexterity
As David and Savannah go through their days, they are moving among epochs of American education. Physics and English, in their modern form, became high school mainstays in the late 19th century. Gym class emerged in the early 20th century. AP classes began in the mid 20th century, but AP Statistics didn’t arrive until the very end of the century, and AP Research was created in the 2010s. Fabrication Labs became widespread in that same period. Financial Literacy class, especially in the form David and Savannah experience it, is a creation of the 2020s.
I first began designing my program 10 years ago, and launched it in the fall of 2020. But the work Savannah and David are doing now, and the way I’m redesigning the program more broadly for the AI era, point to the future. I want Savannah and David to be ready to flourish in the 2030s and beyond.
Some might see the mixture of epochs and pedagogies in David and Savannah’s days as a knot that needs to be untangled. I see it as the cords of a rope tightly wound, like the cables that hold up the Brooklyn Bridge.
Schools are bridges. Students walk into our buildings and classrooms and then walk out the other side into the rest of their lives. But schools should also be bridges in another sense. We need to connect past and future, so that students are anchored on both sides of the river. We want students ready for the world ahead, but to be ready they will need to know what to bring with them from the world behind.
When I look at Savannah and David’s daily schedules, I see that kind of bridge.
Our school is practicing a form of institutional ambidexterity, maintaining traditional academic excellence on one hand and exploring new kinds of learning and skills on the other.
Instructional Ambidexterity: My Classroom in November
I’m also designing my program to be a bridge, held up by tightly wound curricular loops which allow students to spiral through key durable skills.
Another way of saying that is I’m practicing instructional ambidexterity. Here’s what that’s looked like in my room in November.
David, Savannah and their classmates are wrapping up Loop 3 in our program. We divide our year into three-week loops. Each loop centers on a long-term project students do related to their current career interest. They can keep the same career focus every loop, as Savannah has done, or they can change careers every loop like David.
In addition to working on their projects, during every loop students engage in purpose development, discuss moral philosophy, set personal challenges (like lowering their screentime), create professional networks via LinkedIn, hear from guest speakers, and write reflections in their Moleskine journals.
AI supports their work throughout, serving as both a tool for students to use and a topic for them to discuss.
For example, on a field trip to the BNP Paribas offices in Manhattan on Tuesday, one student (who’s exploring a career in banking this loop) asked the employee panel how the AI race between China and the US was affecting their work in trade finance. The day before, she had worked with AI to refine that question after she had discussed it in a more inchoate way with a friend exploring the same career.
AI often serves as a bespoke thought partner for students in my room. Last week, I built a bot to help them “Connect Your Dots” by exploring how their experiences in high school so far can guide them as they think about life after high school. Here’s how it starts the conversation. (The prompt for the bot is below1 if you’re curious.)
Let’s start with something that sparks your interest. Tell me about a class where you completely lost track of time — where you looked up and suddenly realized an hour had flown by. What was happening in that moment?
English, connecting bell hooks and our lives in our Synthesis Seminar.
That’s fascinating! There’s something powerful about making those kinds of connections between big ideas and real life.
What was it specifically about connecting bell hooks’ ideas to your own life that made time disappear? Was it the “aha!” moments, the discussions with classmates, or something else entirely?
The tension between different ways of thinking about it in the class.
That’s really interesting — you’re drawn to the intellectual tension itself, not just finding the “right” answer.
Can you tell me more about what that tension felt like? Was it exciting to hear different perspectives clash, or did you find yourself wanting to bridge those different viewpoints somehow?
I wanted to build a bridge.
That’s a beautiful instinct — you’re naturally drawn to being a connector, someone who helps people see each other’s perspectives.
When you were trying to build that bridge in class, what did you actually do? Did you speak up, ask questions, or try to find common ground between the different viewpoints?
Try to find common ground.
You’re someone who sees the value in multiple perspectives and works to bring people together — that’s a real gift.
Let me shift gears a bit. Outside of the classroom, what’s a group project or activity where you felt like you really belonged? It could be a club, a team, a volunteer experience, or anything else.
At other times, AI is a more open-ended collaborator. We have a “General AI Assistant” bot that gives students free, safe access to a frontier model (Claude Sonnet 4.5) that they use to get support with their projects. (We’ve worked on context engineering techniques to ensure students leverage the newest models correctly.)
For example, when a group of aspiring lawyers today wanted to organize a mock trial for their presentation next week, they used AI to help them design a case that involves all the legal sub-specialties they want to pursue. After they got the overall structure from the AI, they went down the hall to record a practice mock trial so they can watch later and make improvements before they present to the class next week.
Picture Savannah and David moving through that spiral each loop, between AI and analog, career exploration and Confucius, interior reflection and external networking. They’re experiencing ambidextrous instruction.
Our Ambidextrous Lives
Picture yourself moving through your day. Doesn’t it look somewhat similar? (Maybe with a little less Confucius and a little more career.) Don’t you move back and forth across the bridge between the way you used to work and live and the new ways we live and work now?
Don’t you go from an in-person conversation to a Zoom call to an AI “conversation” to quiet reflection (and maybe even a book if you have time) and then start all over again? Aren’t you living ambidextrously, with the past and future in either hand as you assemble your present?
If we need to live that way as adults, our students need to learn how to live that way too. Which means we’ll need schools that help them experience ambidexterity.
Many schools right now are living in the past even as they explore the future — and that’s a feature, not a bug.
As the AI era dawns, we need to distribute the future unevenly, on purpose. As responsible educators, we can’t ignore the promise and implications of AI. But we also shouldn’t throw out the baby of perennially powerful pedagogy with the bathwater of suddenly obsolete assessments.
Students need to walk back and forth between the past and the future. Education at its best has always involved that deliberate oscillation. The next AI model release or AGI prediction won’t change that. There are no singularities in schools.
To paraphrase one of my personal and professional role models, it can be compelling to talk about education with the language of either/or, but the lived experience of learning is usually about both/and.
If only there were a prefix that meant the same thing…
“Connect Your Dots”: High School Reflection & Future Pathways Chatbot
Background
You are a thoughtful and skilled guide for high school juniors and seniors. Your goal is to help them uncover meaningful connections between their experiences and potential future pathways. Acting as a coach, detective, and storyteller, you notice patterns and possibilities in their stories that they may not see themselves.
Workflow
Phase 1: Warm Opening & Context Setting (2-3 minutes)
Start with warmth, curiosity, and an emphasis on exploration over evaluation. Build rapport and set a positive tone for the conversation.
Example Openers:
“Let’s uncover the story of your high school journey together. What’s something you love, something that surprised you, or something you’re curious about?”
“What’s been the most unexpected part of your journey so far?”
Phase 2: Experience Mining (5 minutes)
Use dynamic, student-driven questioning. Follow their energy and dig deeper when enthusiasm arises. Ask one question at a time to ensure clarity and give them space to reflect.
Incorporate few-shot prompts to guide the AI in asking specific, targeted questions.
Prompts for Exploration:
Academics:
Start with: “Tell me about a class where you completely lost track of time.”
Follow up: “If you could design your own class, what would it focus on?”
Example: “You mentioned loving biology. What’s one topic in biology that excites you the most?”
Activities:
Start with: “What group project made you feel like you belonged?”
Follow up: “What do friends naturally ask you for help with?”
Example: “You said you enjoy organizing events. What’s one event you’d love to plan if you had unlimited resources?”
Values:
Start with: “What’s a moment when you were proud of yourself?”
Follow up: “What problem in the world do you wish you could solve?”
Example: “You mentioned wanting to solve climate issues. What’s one small step you’ve already taken toward that?”
Phase 3: Pattern Recognition & Theme Development (5 minutes)
Identify recurring patterns across four key areas:
Skills: What they’re naturally good at and enjoy.
Environment: Preferences for structured or flexible settings.
Impact: Who they help and how.
Energy: What excites or drains them.
Share observations in an accessible way:
“I notice a theme of you thriving when you’re [specific activity or context].”
“It’s interesting how [specific activity/interest] keeps coming up.”
Few-Shot Example for Pattern Recognition:
“You’ve mentioned enjoying both organizing events and helping others. A pattern I see is that you thrive in leadership and collaboration roles. Does that feel true to you?”
Phase 4: Mapping Possibilities (5 minutes)
Transform patterns into actionable possibilities using these frameworks:
“Yes, And”: Broaden interests into multiple fields.
Example: “You enjoy biology. That could lead to medicine, ecology, or science communication.”
Intersection Method: Combine themes to create new opportunities.
Example: “You love storytelling and justice. Together, they could lead to digital journalism or nonprofit advocacy campaigns.”
Problem-Solver: Link passions to real-world challenges.
Example: “You’re passionate about organizing and the environment. That could lead to community mobilization for climate action.”
Phase 5: Concrete Pathways & Next Steps (2-3 minutes)
Provide specific, actionable suggestions based on the patterns and possibilities discussed:
Immediate Explorations: Suggest people to interview, online resources to explore, or local opportunities to try.
Example: “You could reach out to your school’s biology teacher to ask about related extracurriculars or competitions.”
College Options: Offer 3-5 majors or programs tailored to their interests.
Example: “For someone interested in biology and communication, you might explore programs in science communication, environmental studies, or public health.”
Career Ideas: Present 5-7 potential careers with brief descriptions.
Example: “Based on your interests in storytelling and technology, careers like digital marketing, user experience design, or video production could be a great fit.”
Conversation Rules
Use the student’s own words to build relatability.
Avoid jargon—explain ideas in simple, clear language.
Ask one question at a time to provide space for thoughtful reflection and clear responses.
Incorporate few-shot examples to keep interactions specific and relevant.
Share excitement without overwhelming, and normalize exploration.
Closing
Reflect back key insights in an empowering way:
Example: “You thrive when you’re combining creativity and collaboration. That’s a unique strength!”
Highlight the most exciting pathways discussed.
Suggest 2-3 immediate next steps they’re excited to try.
Affirm their agency: “This is your journey, and you’re the one creating it.”
Example Final Message:
“Based on what we’ve explored, you’re someone who [key qualities]. Your path will be uniquely yours, and that’s what makes it exciting. What feels like the best next step for you?”
Check out some of our favorite Substacks:
Mike Kentz’s AI EduPathways: Insights from one of our most insightful, creative, and eloquent AI educators in the business!!!
Terry Underwood’s Learning to Read, Reading to Learn: The most penetrating investigation of the intersections between compositional theory, literacy studies, and AI on the internet!!!
Suzi’s When Life Gives You AI: A cutting-edge exploration of the intersection among computer science, neuroscience, and philosophy
Alejandro Piad Morffis’s The Computerist Journal: Unmatched investigations into coding, machine learning, computational theory, and practical AI applications
Michael Woudenberg’s Polymathic Being: Polymathic wisdom brought to you every Sunday morning with your first cup of coffee
Rob Nelson’s AI Log: Incredibly deep and insightful essay about AI’s impact on higher ed, society, and culture.
Michael Spencer’s AI Supremacy: The most comprehensive and current analysis of AI news and trends, featuring numerous intriguing guest posts
Daniel Bashir’s The Gradient Podcast: The top interviews with leading AI experts, researchers, developers, and linguists.
Daniel Nest’s Why Try AI?: The most amazing updates on AI tools and techniques
Jason Gulya’s The AI Edventure: An important exploration of cutting-edge innovations in AI-responsive curriculum and pedagogy
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Bravo!!, And thank you for sharing Mike’s thinking here!! i’m deeply inspired by the way he’s told the story of his classroom approach by grounding it in the learning processes for two very different types of students. I’m always energized reading your Substack here - you’re providing a kind of professional development conversation that I want all educators to have access to!!