Hey,
It’s been a minute, but this week I hit a tech wall. As in the laptop just did not want to stay on my lap. It just wanted to be left alone for a few days. And I thankfully obliged. I worked in the garden, listened to an incredibly red cardinal sing to a friend a few blocks away, watched a hawk get messed with by angry crows, read snippets from a few of my favorite books, took a couple of long walks, and pretty much just shut down the world for a spell.
It was really, really nice.
Actually, it kinda scared me how nice it was. I’m not one to run from the trouble, as they say, but the trouble has been piling kinda high lately, no? And yet there is good work to do. But maybe after some more downtime, which is allowing me to explore even deeper connections with all the life around me. Much needed.
All of which is to say, here’s a semi-shortened gloss of interesting links this week. I gotta get back outside. (NOTE: It didn’t end up that “short”!)
SUMMER REGISTRATION OPEN!: Reminder: My Confronting Education Workshop is now open for registration. I hope you’ll consider joining us for Cohort 5 of the workshop, which starts on June 26. If you’re feeling all the world craziness and the struggles education is having to deal with it, you’d be in the right place. Early Bird pricing through May 15. Reach out with questions.
FINALLY: As always, thanks for reading. As a reminder, all posts here are free, but if you want to show your support for my work in general, a paid subscription is always an option. Remember: I’m donating all proceeds from paid subscriptions to my local food pantry ($247.50 so far for 2026…) at the end of the year.
With gratitude,
~Will
Few are more direct than Rachel Donald when it comes to a frank articulation of the shit we’re in. And, if you read the intro above, you’ll understand why this piece resonates, especially the first couple of paragraphs:
“I am exhausted by “content”, so much of which is vacuous. I am exhausted by the sense of keeping up when my own philosophy insists we all need to slow down. I am exhausted by the false sense of competition with peers I admire that algorithms create. I am exhausted by the meaningless and just how much attention it demands. I know I’m not the only one who is exhausted. I know so many of you are, just as everyone I know and love is. Keeping up is impossible, and yet there is nowhere to turn. We are witnesses to history, and yet, as ghosts will tell you, witnesses are history’s victims, too.”
I wrote that in December, for the launch of this new site which I hoped would provide a place of quiet introspection on the vast internet, and even provoke a bravery in me to step off the content-production treadmill. Yet, here I am, months later, still desperately trying to keep up so that all of you may find value in what I do, even when there is nothing I could say which would illuminate any better this interminable moment in history in which everything is coming apart.
I don’t claim to be in Rachel’s league when it comes to sharing important wisdom as to how we navigate the world right now. But that “desperately trying to keep up so that all of you may find value in what I do” just hits home perfectly right now.
And while I know this next snip is intense, it touches on something that I know many are feeling right now, a sense of being disconnected from the collapse we know is happening right now. This struggle also resonates.
And it is all senseless—not just because of the utter meaningless and arbitrariness of the violence inflicted against the world, but because we cannot feel it in each other, and if I cannot feel it in you then I cannot feel it in me. I am experiencing the singularity of collapse through digital code and algorithms and this is making it harder and harder for me to locate the pain that is screaming for attention somewhere inside me. And yet, those of us for whom the crisis is still digitised are the lucky ones, because the crisis is a rainstorm of missiles elsewhere in the world, or a ravaging hurricane, or a drought. This crisis is an embodied crisis, blasting children into pieces and turning rivers into sand. Those of us who cannot yet locate this crisis in our bodies are fortunate because it means our suffering is not yet so acute that the entire future has bled out. But surely there has to be some other instance of feeling—a moment or a state between agony and anxiety. Surely there has to be some way to feel this in one another and through one another. Surely there is a way to feel the very collective nature of this global singularity so that even for a moment we do not feel alone with it?
How do we feel it without the literal harm that collapse is already bringing to so many?
This is a hard read, but I think it's worth it.
I struggled with sharing this piece from the Stanford Social Innovation Review because while on the one hand, it includes some good thinking about the shift we’re undergoing when it comes to the impacts of AI on the value of being human, on the other it focuses almost exclusively on “human flourishing” and inter-human relationships while totally ignoring how we must learn to relate more deeply with all other life on the planet.
Sigh. Kind of misses the point.
That said, it still has a good deal of thought value:
We are entering a pivotal evolutionary moment. The defining challenge of our time is not whether artificial intelligence will advance—it will—but whether we will intentionally cultivate the RQ [relational intelligence] that makes those advances serve human flourishing, rather than undermine it. In an era marked by loneliness, fragmentation, and the substitution of technology for human presence, RQ is both under threat and newly indispensable. The future of learning, work, health, and democracy will depend less on how smart our machines become and more on how well we design our lives and institutions to strengthen human relationships.
To meet this moment, we must invest not only in new technologies but in relational infrastructure: the intentional design of environments, schools, workplaces, health systems, communities, and digital platforms to make human connection the default, not the exception. It reallocates time from individual output to mutual presence, replaces isolation with connection, and transforms care from a private burden into a public good. At its best, relational infrastructure strengthens learning, resilience, trust, and collective problem-solving. In its absence, loneliness rises, institutions fail, and technology rushes in to simulate what society no longer supports. Building relational infrastructure is not a soft aspiration; it is a hard requirement for human flourishing in the age of AI.
As I said, there is much more to it than that, I think, but becoming more relational in any form is a good start.
The Green School in Bali is a rare example of a school that is committed to balancing (to whatever extent it’s possible) some of the grammars of traditional schooling with a fundamentally different answer to the “In service of what?” question that I ask all the time when I run across “innovation” in schools. In this post at LinkedIn, the Head of Upper School Benjamin Freud does a really nice job of clarifying what they mean when they say “regenerative education” as a focus of schooling for a fracturing world:
Schools love talking about student voice. Yet what’s the point of having a voice if no one is listening, or no one is hearing? A seat at the table doesn’t mean anything unless you’re a diner.
Regenerative education emerges when young people shape their school: Through participation in policy-making and implementation, diffused decision-making, curriculum and organizational decisions. Everything that is non-confidential.
This creates new possibilities for a healthy ecosystem.
And learning. Is there any deeper learning than participation, in real time with real situations and real consequences?
Students as representatives regularly invited to leadership meetings as full voting members
Suggesting, writing, and implementing policies about academic and school life
Being part of curriculum design committees
Participating in the hiring decision of every educator
Having a lead role in organizing events.
Playing their part to care for the physical grounds
Sitting on disciplinary committees
This is what makes a school alive: responding, adapting, growing, which is just what the living world does.
And here’s a somewhat related bonus link that highlights the work of United World College and its “Systems Transformation Pathway,” a pilot program from the IB which I’ve glossed in this newsletter previously. The case they make for the shift to a much different experience of school is pretty profound:
There is a growing chorus calling for transformative change in global education, yet the system itself remains stubbornly resistant. Bureaucratic inertia, outdated assessment structures and political polarisation all play a role. But we must be honest: sometimes it is simply easier to maintain the familiar than to admit that it no longer serves its purpose.
We cannot afford that comfort any longer. To continue educating young people for a world that is disappearing is a profound failure of responsibility. We are preparing them for stability while handing them instability. We are training them for linear career paths while they are entering nonlinear realities. We are teaching them to solve problems in isolation while the world demands collaborative, cross-disciplinary and globally minded thinking.
Focusing on five key impact areas: food, biodiversity, energy, migration and water, the pathway moves beyond traditional subject silos. Instead, it teaches students how environmental, economic, social and political systems interact, how climate influences migration, how governance affects resource distribution and how technology shapes identity and power. With this comes a deep emphasis on resilience, ethical leadership and agency. Students are not treated as passive learners, but as emerging systems transformers capable of engaging with the world’s challenges now, not someday in the future.
Two good reads to get you thinking about real school change.
How do we *actually* emerge our way into “the what comes next”? - Great conversation between Sarah Wilson and Samantha Sweetwater
What to expect when you’re expecting the end of the world - More from Jem Bendell
Wondering: Do we really have any idea how harmful to the Earth, to ourselves, and to one another our most embedded practices are? We’re so addicted to convenience…
Civilizational Optionality - Really good. I may have to revisit this in depth next week.
Seminole Nation Becomes First Indigenous Group to Ban Planet-Cooking Data Centers From Its Land - Lots to love about this.
As always, let me know what you’d like to see more (or less) of in these newsletters. I’m always open to learning and evolving in ways that help you make better sense of this interesting moment.
With gratitude,
~Will

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