The week of December 7, Kaile and I attended the national Learning Forward Conference in Boston, Massachusetts. While the weather was a reminder that we were far from Hawaiʻi, the conversations were anything but cold. Across three days, a set of powerful through-lines emerged—about leadership, systems, voice, and what it really means to keep learning centered on students in uncertain times.

The conference opened Monday morning with a keynote from Cornelius Minor, Keeping the Focus on Kids in Uncertain Times. Minor grounded the week in a moral imperative: when systems feel stressed or unstable, the temptation is to retreat into control and compliance, but our responsibility is to double down on relationships, humanity, and care. His message was a steady reminder that equity work begins with how we see children—and whether our decisions consistently reflect that focus.

That idea of systems shaping experience carried directly into our Monday morning session with our friends at the High Tech High Graduate School of Education team, Process Mapping Your Way to Better Systems, which drew on work from the National Coalition for Improving Education. Rather than treating dysfunction as a people problem, the session invited us to look closely at processes—how work actually moves through a system, where friction shows up, and how well-intentioned structures can quietly undermine learning. It reinforced a recurring theme of the week: experience is the system. During the session, I spent time reflecting more deeply on our process for coaching calls with teams of teachers. Time well spent!

Monday afternoon’s workshop, “Core, Contingency, and Paradox: Leading Systems for Continuous Improvement,” by Jal Mehta reframed school improvement as human, not technical, work. Drawing on complexity science and Margaret Wheatley’s Six Circle Model, he emphasized that sustainable change requires attention both above and below the “green line.” Structure, process, and strategy matter, but relationships, identity, trust, and shared meaning are what allow improvement to take root. Mehta challenged leaders to match approaches to the type of problem they face and to live within productive tensions—action and reflection, order and emergence. Improvement, he argued, is less about control and more about learning our way forward.

Tuesday morning began with the keynote Pedagogy of Voice: Street Data and the Path to Student Agency from Shane Safir and Sawsan Jaber. Their work reframed data as something gathered through listening rather than extracted through dashboards. Student voice, they argued, is not feedback—it is access to power, belonging, and authorship. Crucially, they emphasized symmetry: if we want agency for students, adults must experience it as well.

That notion of symmetry carried into Tuesday morning’s session, Leading for Deeper Learning, led by Melissa Daniels and Stacy Lopez from High Tech High GSE. They challenged leaders to examine whether adult learning truly mirrors the inquiry, collaboration, and reflection we value for students. School culture, they reminded us, is shaped less by vision statements and more by the daily experiences people are invited into.

Tuesday afternoon brought us closer to home with Transform Your School Through Collective Action, led by Joe Passino, principal of Princess Keʻelikōlani Middle School in Honolulu, and Bette Moreno. We were proud to hear how their leadership moves—high expectations paired with high support, visible collaboration, and shared responsibility—are shaping student commitment and learning. Their work made clear that transformation is not driven by heroics, but by culture built collectively over time.

Wednesday morning, we closed our conference experience by facilitating our own session on AI for Equity and Deeper Learning. Rather than positioning AI as the work itself, we framed it as a mirror—one that reveals values, assumptions, and design choices. The thoughtful engagement of participants suggested the field is ready to approach AI with discipline and purpose, not hype.

I left Boston encouraged. Across sessions, the message was consistent: deeper learning emerges when we align systems, culture, and leadership around humanity, voice, and agency—for students and adults alike.

As we navigate the growing presence of AI in education, I keep coming back to the comic strip Calvin and Hobbes. In particular, the way Hobbes never handed Calvin the answer—he leapt into the cardboard box with him, launching toward Saturn, getting lost, making meaning. That’s the spirit I hope we hold onto as we consider how AI might walk with us rather than think for us. Here’s a reflection on curiosity, imagination, and the kind of company we choose on the learning journey.

“Learning isn’t about knowing the path—it’s about building the courage to walk it, with just enough company to keep you wondering.”

There’s a Calvin and Hobbes strip that’s always stuck with me. Calvin raises his hand in class and asks, “May I be excused, please? I need to go bad?” The teacher says yes. Next frame, he’s walking into his house, and his mom’s staring at him, bewildered. “What are you doing home?” she asks. “I had to go,” Calvin says.

It’s perfect. Calvin’s imagination couldn’t be contained by classroom norms. When the structure didn’t speak to his curiosity, he left—and we laugh, because deep down we get it. There’s a wildness in learning that systems too often try to tame. And no one gets that better than Hobbes, Calvin’s tiger co-pilot, who doesn’t hand him answers but pushes him to explore every cardboard-box idea he dreams up.

Lately, I’ve been wondering: what if AI could be more like Hobbes?

That question hit me as Alex Hutchinson explain his new book “ The Explorer’s Gene”, where he talks about the human drive to explore, to wander, to not know what’s around the next corner. He and David Epstein dig into how our brains and bodies are wired for exploration—and how much we lose when we optimize too soon, or choose comfort over curiosity.

And then I read Ethan Mollick’s post The Cybernetic Teammate. He makes a compelling case that the best uses of AI don’t replace people—they expand them. AI, in his view, isn’t a faster calculator or a clever shortcut. It’s a teammate. One that nudges, reflects, and helps you think in broader, more interdisciplinary ways. In other words…a Hobbes.

But here’s the danger: If we bring AI into schools and workplaces without that Hobbes-like spirit, we risk shrinking the very range of human exploration. We’re already doing it. We’ve gone from kids roaming six miles from home to barely 300 yards. And that same constriction is happening intellectually—when we rush students through hard questions, when we Google instead of grappling, when we mistake speed for insight.

In my own teaching, I didn’t always have the courage to admit I didn’t know something. But over time, I learned to model curiosity instead of certainty. Teaching electronics, for instance, we’d run into things I didn’t fully understand. Instead of bluffing, I’d sit beside students and say, “Let’s figure it out.” We’d poke at the black box—literally and metaphorically—and uncover the systems beneath. That, to me, is real learning: not having the answers, but being willing to stay in the question.

And that’s how I’ve come to see the potential of AI—especially when it’s designed and used with intention. Right now, in this creating this post, , I did not ask AI to give me something. I used it to stretch my own thinking. To reflect, wonder, and wander. And it worked—not because it’s efficient, but because it’s relational. It’s walking with me.

If we want AI to support human growth, not replace it, we need to treat it less like a productivity tool and more like a thoughtful co-learner. We have to trust that students—and adults—will do the hard thinking when they’re given something worth thinking about. We need to design learning not around shortcuts, but around meaning. That’s the promise. And the risk.

Because in the end, learning isn’t about knowing the path—it’s about building the courage to walk it, with just enough company to keep you wondering.

So maybe it’s not about the journey or the destination.

Maybe it’s the company.

And the best kind of company doesn’t do the walking for you. It walks beside you—like Hobbes—laughing, nudging, imagining, and daring you to explore.

As we approach the end of another school year, teachers look forward to a few precious weeks of summer to reflect, recuperate, and prepare for the upcoming fall. This period is an excellent time to consider how our students learn and, even more importantly, how our teachers grow in their practice. For those of us who advocate for deeper learning, it’s clear that there are structural issues with how teachers develop professionally and how adolescents are taught in schools.

The problem partly stems from a long history of schools being designed around a “Tell, Show, Do” approach. While there’s nothing inherently wrong with this method, it often creates a gap between telling, showing, and doing. As a former Boy Scout assistant scoutmaster, I’ve seen firsthand how skills like using a knife, administering first aid, or leading a group are taught using this approach. However, the challenge lies in the delay between the different stages of learning.

Consider learning to ride a bicycle. We wouldn’t spend years teaching about all the parts, testing for understanding, and separating components like wheels and pedals from balance. We certainly wouldn’t wait long between showing and letting the learner practice. Yet, in both teaching and student learning, we often focus extensively on individual parts without letting them play the whole game. The line “when do we use this information?” has been part of the student voice for a long time. Historically, learning happened through mentorship and apprenticeship, where learners worked alongside experts, observed, listened, and practiced actual skills incrementally.

In his book “Learning to Leave,” Elliott Washor argues that effective learning involves dovetailing, doing, showing, and telling in incremental steps without delaying practice. This concept is crucial as we help teachers integrate deeper learning into their work. Providing opportunities for them to practice is essential.

In an article about microcosms of practice, Jal Mehta advocates for teachers starting with a unit (a microcosm) to experiment with pedagogical and assessment practices in deeper learning, whether it’s project-based learning, inquiry, place-based learning, design thinking, or other student-centered approaches.

This leads to the central idea of this article: if we truly learn best by doing, how do we ensure that this happens in our professional learning? One approach is providing teachers with opportunities to practice their new skills in the classroom. This summer, we will work with a group of teachers from Nānāikapono Elementary, introducing them to deeper learning design concepts and then observing, sharing, and building on what works during their four-week summer program. This summer lab approach offers a rich opportunity to just do it, with support and opportunities to learn from and refine practices that enhance engagement, evidence collection, and learning in their classrooms. As Dewey said “we don’t learn from experience, we learn from reflecting on experience.”

Research shows that experience increases teachers’ effectiveness and efficacy. One of our biggest challenges is giving teachers the chance to not just be told or shown new teaching methods but to put them into practice. It’s time to just do it!

The term “Permanent White Water” comes from Peter Vail’s “Learning as a Way of Being (1996) and has always been a powerful metaphor for ongoing change, and never more true than at this moment.

Navigating The White Water with Deeper Learning

Much like the waters of the Hawaiian Islands, deeper learning comprises moments of turbulence, tidal pulls, following seas, and sweet rides on waves – if you can catch them! It’s about reading the water, grappling with real-world challenges, and emerging with an enduring understanding. In our journey at Kupu Hou Academy, we’ve always emphasized the importance of being present, of truly immersing oneself in the learning experience, whether it’s understanding the complex interdependence of our local water systems or the intricacies of a mathematical concept. At its core, deeper learning, as described by Mehta and Fine in the book “In Search of Deeper Learning” revolves around the pillars of “Identity, Mastery, and Creativity.” It’s not just about acquiring knowledge; it’s about forging a strong sense of self, mastering complex skills, and channeling that mastery into creative endeavors. It is this kind of learning that makes knowledge powerful, transferable and engaging.

AI: The New Current

Enter AI. This technological marvel promises to revolutionize education and be disruptive to entrenched systems and past methodologies and beliefs about teaching and learning. As champions of student-centered learning, how does it fit into our deeper learning framework? Can it enhance the richness of our learning experiences, or will it merely streamline them, potentially robbing us of the ‘grappling’ essential to true understanding?

Imagine a classroom where AI-driven platforms adapt to each student’s learning style, providing real-time feedback and challenges tailored to their current understanding. It’s not about making the journey smooth; it’s about ensuring it is meaningful and aligned with the learner’s “just right” feedback and support.

The Confluence of Culture and Technology

Drawing from our experiences, like the insights gained from indigenous perspectives managing and appreciating water, it’s essential to approach AI with a balanced view. Technology, when integrated with cultural and local contexts, can provide a richer, more holistic learning experience. The stories, the narratives, the connections – they all matter. And AI when used as an adaptive tool can help weave these threads together, creating a tapestry of learning that’s both deep and wide.

Charting the Course Ahead

As we navigate these turbulent waters, it’s crucial to have a clear sense of where we are going. Much like the attached picture (that’s Mark steering a crew off Manana Island near Sandy Beach on Oahu) we need to read the waters we are in AND have a commitment to the ultimate destination we are heading to. Just as we have supported hundred of teachers over the past years in developing meaningful projects and inquiries for their learners, integrating AI into education requires clear goals (Got a good Essential Question?), purposeful learning, assessment criteria, and continuous feedback. We need to ensure that our students not only reach their destination but also cherish the journey.

The fusion of AI with deeper learning presents both challenges and opportunities. As educators, it’s our responsibility to ensure that we harness the potential of AI while staying true to the principles of deeper learning. The journey promises to be exciting, and I invite all educators, students, and tech enthusiasts to join us as we chart this new course.

**This draft was supported by conversations with ChatGPT on August 13, 2023

Reference:
Vaill, Peter B. Learning as a Way of Being: Strategies for Survival in a World of Permanent White Water, San Francisco: Jossey-Bass, 1996.

Mehta, Jal, and Sarah Fine. In Search of Deeper Learning: The Quest to Remake the American High School. Cambridge, MA: Harvard University Press, 2016.

(This post a reflection from a class visit from our Kumu (Teacher) Makana Kane Kuahiwinui, who spoke to us about the Hawaiian cultural perspective on water, in general and specifically in our Manoa Valley.)

The work we have been doing and thinking about water consumption at times seem disconnected from a real problem, situation and solution. Kumu’s sharing today broadened my thinking because I usually see most things through a western science perspective. Is it dirty? How do we know? How can we clean it? I deepened that meaning by really backing up and considering what the water all around, the rain (Tuahine) we see every day, the running water on campus, Wailele and how it sits with Kahala O Puna in the middle of campus. I need to recommit myself to not just going for learning information but learning to be present in this moment and know why and how it matters.
The connection to this place in Manoa is something that we can do something about if that speaks to us. The importance of how water is around us and why and what we could do with it is a lesson and a challenge. And an opportunity.

I also think that the idea of ‘amakua and the importance of Pueo is interesting. The fact that Hawaiian culture speaks of the importance of a generational tie to what might be our guardian’s ties to families and their histories binds us together to this land.

Lastly I am struck by the importance of story. The value of connecting events, places, people through a compelling narrative is a uniquely human characteristic. I can do better job of using stories as a means to conveying ideas, values, concepts, etc. I should find more storytellers to help engage and tie together our work… Who might this be?
What was my wish for Wailele? That I don’t go by without checking in on her and asking how we are doing with her. We, our students, can visit and ask “how are you doing, how are WE doing?”