In the tech world right now, the hottest idea in education is AI tutoring. Personalized, mastery-based, infinitely patient digital guides — the dream is that every student could have the kind of one-on-one tutor once reserved for royalty. It’s a compelling vision, and experiments like Alpha School show the kernel of truth: students really do learn more when they progress at their own pace, with tailored support.

But here’s the trap: if we treat AI tutoring as the end point of education’s evolution, we shrink the horizon. We mistake the means for the goal. Education has never been only about individual knowledge acquisition. Education is often framed as the transfer of knowledge — a body of facts, a sequence of skills, a curriculum to be consumed. But the truer image is older: learning begins with lighting a fire.

Think of being a kid at a friend’s house, watching their dad fix an engine or carpenter a cool table out of a piece of wood. You didn’t just learn that a carburetor existed. You glimpsed a world where you might one day shape steel, solve problems, make something awesome with your own hands. Or see someone start a business out of a garage to use that old trop.

There is always that teacher, whether in school or beyond, who impacts young one's life. Consider the older cousin who volunteers at night for the local emergency rescue and modeled what civic responsibility looks like. Or the retired teacher who runs a poetry night at the library, showing that literature isn’t confined to textbooks but alive in your neighborhood. That lights a spark

John Dewey reminded us that the highest purpose of public education is the cultivation of “the Great Community” — continuous learning embedded in shared life, where students are not just future workers but present citizens.

So the challenge is to reimagine school not only as a personalized path but as a porous community fabric. That’s where ideas like “free range kids” point the way: less helicoptering, more trust, more exploration. What if school days themselves were rewilded in this spirit, with students moving through neighborhoods, gardens, libraries, workshops, and civic spaces — while AI tutors ensured that their learning stayed coherent and cumulative?

The real frontier is not AI tutors reshaping the classroom, but how AI tutors and the broader connectivity that 3web enables to reimagine community. When students are allowed to roam — free range not just in fields, but through the arteries of community life — they encounter role models, skills, and civic forms that textbooks cannot simulate.

• Apprenticeships with local tradespeople teach that math lives in carpentry, physics in plumbing.

• Participating in city council youth forums shows that governance is not an abstract unit in civics, but a messy, living thing.

• Working in community gardens reveals how biology and ecology intertwine with neighbors’ daily meals.

• Interviewing elders at the senior center makes history less about dates and more about lived experience.

• Shadowing a lawyer at the courthouse shows how rhetoric, precedent, and justice collide in the everyday work of society.

• Visiting a rocket lab or aerospace firm makes physics no longer abstract equations, but the real engineering of escape velocity and orbital mechanics.

• Helping a local nurse in a community clinic brings anatomy, chemistry, and compassion into the same frame.

• Joining a reporter at the local paper demonstrates that literacy is not just reading novels but shaping the civic narrative.

• Sitting with an architect at a drafting table reveals how design, math, and imagination converge to shape skylines.

• Volunteering with a startup founder shows entrepreneurship as both risk and invention, not just a word in an economics textbook.

• Rehearsing with a theater troupe teaches collaboration, memory, and the art of telling truths through fiction.

• Spending time with coders at a hackathon grounds abstract algorithms in real tools.

• Shadowing a biologist at a watershed or nature reserve makes ecology a living map rather than a diagram.

In each case, the AI tutor can be there on the side, ready to shore up the algebra, the vocabulary, the background reading. But the spark comes from the encounter with the living community.

Alpha School shows that AI tutors can enable mastery-based learning. But their $50,000 price tag and selective clientele highlight the limits of a purely individualized model. Well that and the idea of Airbnb rentals as the canonical life skills class definitely embeds neo-Victorian attitudes.

If education becomes a boutique service for elites, we will have gained sharper tutors but lost the common square. The next leap isn’t to perfect AI tutoring, but to weave it into a broader vision: schools as community nodes, children as free range learners, education as civic participation.

Ultimately, AI tutoring is only one piece of the puzzle. The broader evolution of the web — what I’ve been calling 3web — already has many of the building blocks we need to connect students to opportunities like these. Scheduling platforms, geospatial data, open civic APIs, collaborative tools, and reputation systems can all be harnessed to thoughtfully and carefully bridge classrooms with communities.

Imagine a system where a lawyer, gardener, or rocket scientist can safely and easily open up shadowing or apprenticeship slots to students, and where schools can fluidly integrate those opportunities into the rhythm of the week. This isn’t science fiction. The architecture exists. What’s required is intention, imagination and ultimately courage.

The need isn't just another app but more deeply how we choose as free people to associate, how we choose to design local schools and weave together how we live, work and play to nurture learning.

I come to this not just from theory, but from practice. Years ago, I served on the board of an education reform nonprofit that predated charter schools. One of its signature programs was Principal for a Day, where community leaders stepped into schools to experience firsthand the challenges and potential within. The idea was simple: schools are not factories or test prep centers, but centers of community. That spirit remains vital now, perhaps more so, as we contemplate what the web and AI can offer.

What would it look like to take that ethos — schools as hubs of civic life — and build it into the digital protocols of this century? To make it normal, not exceptional, that a student’s school day weaves between classrooms, neighbors, and the living city, supported by the connective tissue of the web? That is the horizon worth aiming for.

• 3web: The Frontier Where Digital Meets Dirt
  Opening essay in the 3web series exploring how the digital and physical worlds can meet in practical, community-shaping ways.

• Building Alpha School and the Future of Education (Colossus Podcast)
  Interview about the design of Alpha School — mastery-based learning, AI tutors, and project-based approaches.

• Your Review: Alpha School (Astral Codex Ten)
  Critical reflection: Alpha’s strengths in mastery learning, but also its exclusivity ($50k/year, self-selecting students).

• A Radically Practical Vision of Education (EdSurge) (by yours truly)
  Talks about AI tutors before it was cool, back in 2014. The piece also has a personally resonant motif bridging learning about Roman water systems while playing in the canyons of my hometown.

• 🌱 Seeding the Second Foundation, Vol I: The Edge and the Ember
  Reflection on Edge Esmeralda, a pop-up city experiment blending intentional community with innovation — a living prototype for how education, play, and civic life can intertwine.

In the tech world right now, the hottest idea in education is AI tutoring. Personalized, mastery-based, infinitely patient digital guides — the dream is that every student could have the kind of one-on-one tutor once reserved for royalty. It’s a compelling vision, and experiments like Alpha School show the kernel of truth: students really do learn more when they progress at their own pace, with tailored support.

But here’s the trap: if we treat AI tutoring as the end point of education’s evolution, we shrink the horizon. We mistake the means for the goal. Education has never been only about individual knowledge acquisition. Education is often framed as the transfer of knowledge — a body of facts, a sequence of skills, a curriculum to be consumed. But the truer image is older: learning begins with lighting a fire.

Think of being a kid at a friend’s house, watching their dad fix an engine or carpenter a cool table out of a piece of wood. You didn’t just learn that a carburetor existed. You glimpsed a world where you might one day shape steel, solve problems, make something awesome with your own hands. Or see someone start a business out of a garage to use that old trop.

There is always that teacher, whether in school or beyond, who impacts young one's life. Consider the older cousin who volunteers at night for the local emergency rescue and modeled what civic responsibility looks like. Or the retired teacher who runs a poetry night at the library, showing that literature isn’t confined to textbooks but alive in your neighborhood. That lights a spark

John Dewey reminded us that the highest purpose of public education is the cultivation of “the Great Community” — continuous learning embedded in shared life, where students are not just future workers but present citizens.

So the challenge is to reimagine school not only as a personalized path but as a porous community fabric. That’s where ideas like “free range kids” point the way: less helicoptering, more trust, more exploration. What if school days themselves were rewilded in this spirit, with students moving through neighborhoods, gardens, libraries, workshops, and civic spaces — while AI tutors ensured that their learning stayed coherent and cumulative?

The real frontier is not AI tutors reshaping the classroom, but how AI tutors and the broader connectivity that 3web enables to reimagine community. When students are allowed to roam — free range not just in fields, but through the arteries of community life — they encounter role models, skills, and civic forms that textbooks cannot simulate.

• Apprenticeships with local tradespeople teach that math lives in carpentry, physics in plumbing.

• Participating in city council youth forums shows that governance is not an abstract unit in civics, but a messy, living thing.

• Working in community gardens reveals how biology and ecology intertwine with neighbors’ daily meals.

• Interviewing elders at the senior center makes history less about dates and more about lived experience.

• Shadowing a lawyer at the courthouse shows how rhetoric, precedent, and justice collide in the everyday work of society.

• Visiting a rocket lab or aerospace firm makes physics no longer abstract equations, but the real engineering of escape velocity and orbital mechanics.

• Helping a local nurse in a community clinic brings anatomy, chemistry, and compassion into the same frame.

• Joining a reporter at the local paper demonstrates that literacy is not just reading novels but shaping the civic narrative.

• Sitting with an architect at a drafting table reveals how design, math, and imagination converge to shape skylines.

• Volunteering with a startup founder shows entrepreneurship as both risk and invention, not just a word in an economics textbook.

• Rehearsing with a theater troupe teaches collaboration, memory, and the art of telling truths through fiction.

• Spending time with coders at a hackathon grounds abstract algorithms in real tools.

• Shadowing a biologist at a watershed or nature reserve makes ecology a living map rather than a diagram.

In each case, the AI tutor can be there on the side, ready to shore up the algebra, the vocabulary, the background reading. But the spark comes from the encounter with the living community.

Alpha School shows that AI tutors can enable mastery-based learning. But their $50,000 price tag and selective clientele highlight the limits of a purely individualized model. Well that and the idea of Airbnb rentals as the canonical life skills class definitely embeds neo-Victorian attitudes.

If education becomes a boutique service for elites, we will have gained sharper tutors but lost the common square. The next leap isn’t to perfect AI tutoring, but to weave it into a broader vision: schools as community nodes, children as free range learners, education as civic participation.

Ultimately, AI tutoring is only one piece of the puzzle. The broader evolution of the web — what I’ve been calling 3web — already has many of the building blocks we need to connect students to opportunities like these. Scheduling platforms, geospatial data, open civic APIs, collaborative tools, and reputation systems can all be harnessed to thoughtfully and carefully bridge classrooms with communities.

Imagine a system where a lawyer, gardener, or rocket scientist can safely and easily open up shadowing or apprenticeship slots to students, and where schools can fluidly integrate those opportunities into the rhythm of the week. This isn’t science fiction. The architecture exists. What’s required is intention, imagination and ultimately courage.

The need isn't just another app but more deeply how we choose as free people to associate, how we choose to design local schools and weave together how we live, work and play to nurture learning.

I come to this not just from theory, but from practice. Years ago, I served on the board of an education reform nonprofit that predated charter schools. One of its signature programs was Principal for a Day, where community leaders stepped into schools to experience firsthand the challenges and potential within. The idea was simple: schools are not factories or test prep centers, but centers of community. That spirit remains vital now, perhaps more so, as we contemplate what the web and AI can offer.

What would it look like to take that ethos — schools as hubs of civic life — and build it into the digital protocols of this century? To make it normal, not exceptional, that a student’s school day weaves between classrooms, neighbors, and the living city, supported by the connective tissue of the web? That is the horizon worth aiming for.

• 3web: The Frontier Where Digital Meets Dirt
  Opening essay in the 3web series exploring how the digital and physical worlds can meet in practical, community-shaping ways.

• Building Alpha School and the Future of Education (Colossus Podcast)
  Interview about the design of Alpha School — mastery-based learning, AI tutors, and project-based approaches.

• Your Review: Alpha School (Astral Codex Ten)
  Critical reflection: Alpha’s strengths in mastery learning, but also its exclusivity ($50k/year, self-selecting students).

• A Radically Practical Vision of Education (EdSurge) (by yours truly)
  Talks about AI tutors before it was cool, back in 2014. The piece also has a personally resonant motif bridging learning about Roman water systems while playing in the canyons of my hometown.

• 🌱 Seeding the Second Foundation, Vol I: The Edge and the Ember
  Reflection on Edge Esmeralda, a pop-up city experiment blending intentional community with innovation — a living prototype for how education, play, and civic life can intertwine.