Yes. 1885. Every third weekend in August, the four branches of the family come together to connect, spread out, provide shelter for the young ones, and shade for the elders. The wisest among us have crested 92, with memories that continue to breathe color and life into the pale stories we learned in school.

But this year was different. I was the reluctant leader.

Volun-told by an older cousin in public, I did not have the chance to say no without embarrassing the wisest ones.

Here’s what I’ve come to know: the most powerful opportunities for learning can also be the ones that appear the hardest. They rarely arrive with your consent. They show up disguised as obligation, as inconvenience, as someone else’s idea of what you should be doing — and only later reveal themselves as the exact thing you needed.

I did not raise my hand for this. I was handed it, in front of the people whose opinion of me I care about most. There was no graceful exit. And that, it turns out, was the point. If I’d been given the chance to opt out, I would have taken it — and missed everything that followed.

There are times when you just take the mantle that is passed to you and assume you are ready, even if you don’t think you are. That was the first leadership lesson. But there were others. And I am excited to share them with you.

Leading the People Who Raised You

As the one of the youngest leaders in the family, my team included the beautiful people who raised me. It’s hard to lead those whose feet you used to sit at. But it’s possible.

My father warned me: this is family, not a consulting project. So you will have to learn new skills.

He was not lying.

But like most leaders, I did what I knew how to do. I planned the communications sequence, the follow-up emails, the calendar invites. I scheduled calls with family members who carried influence, and made myself available after the meetings. I prepared for the sidebar objections — the ones with ledgers of justification longer than my years, usually voiced by folks 25 years my senior. I set the agendas. I treated it like a consulting project. I did what I knew how to do.

This experience revealed something about myself. I am open to growth, but the growth must have a purpose and a direction.

I was not interested if it was going to be the same thing. That is not leadership. I was not interested unless we could change direction.

Leadership takes you somewhere you have never been. Leaders take you to the place you never thought you could go.

Familiarity and tradition are such common bedfellows that they create little need to change, reconsider, or reevaluate old ways. If there is any institution that can justify tradition without challenge, it’s family.

Whew.

Growth, however, requires something different. Learning new skills is only relevant when the situation calls for it. New demands emergence. We changed not because we wanted to, we changed because we had to.

Choosing the Ground: Space Matters

Our family’s identity is rooted in the Tidewater. The land we hold was the gathering place for the families. In the 1800s and 1900s in Virginia, black folk could not access public lands. Demonic constraints of white supremacy and segregation made innovation and creativity essential for life, not a superfluous trait that distinguished the highest performers. Our family had enough land to feed people with hogs, butterbeans, tomatoes, and other garden foods. The absence of money was not life threatening because the land feeds. This land was close to the James River. The crabs and the oysters nourished. Peanut-fed hogs salted the earth. With this land, abundance defanged the scarcity of oppression and supremacy. Every body ate. There were no notes.

This was the homeplace.

But we had to change the location. The homeplace was not available. This was the first change.

And there was pushback. Public silence, private dissent. It was not at the home place. The anchor that had provide stability for so long was loosed. For the holders of the tradition, there was concern. If I was the reluctant leader, there were also reluctant followers.

Then the wisest said, “Just tell us what to do and stop asking for feedback. Tell us what we are going to do.” That was so different from the workplace, but it meant that when you are trusted, consensus is an inheritance. That did not mean there was no confusion and no conflict. The RSVP form was not completed.

I soon realized that a Typeform was not the tool for this team. My cousin said, “Just call me and ask.” So instead of relying on the RSVP form, we just used the telephone to get an accurate count. The form that showed only 10 did not account for the phone calls that revealed a more accurate number of 75.

The human touch is always the right touch.

Next, we needed a new place to call home for the day. We used public land. With the home place unavailable, we used a U.S. National Park. But not just any U.S. National Park — the point where the first Africans landed in America, the uncomfortable point where enslaved Black Americans shifted their allegiance to the Union and collapsed the Southern slave economy — Fort Monroe. When America is filled with a family of diligent taxpayers, the use of public lands reduced the cost for everyone. We already pay our taxes. We don’t need to pay twice. Public lands are for the public. So we chose Fort Monroe.

Lastly, we changed the program. Instead of the committee holding the responsibility and the expense to feed everyone, we simply said: bring food for your family, and a dish to share.

Grace would transition from the tradition of a single voice — the pastor’s — to a choral recitation of the Lord’s Prayer.

Acknowledgment of our ancestors would become a public act. Everyone was asked to bring a photo, or something that acknowledged they were here and shared space. We would acknowledge them together.

Then there was the last ask: bring a dish. But not just any dish — the heritage dish from your branch. Bring the dish that says us in a way that only you can. We have to remember what we taste like.

This was the bet. The big bet. Would people come? Would they bring a dish? Would there be enough?

That morning, I woke up early and, with Michelle, endured the regular pre-game anxiety that comes with running any event. We blessed the space with unlit palo santo — it was too windy to catch a flame — and then we just waited.

Then we got the first indication that this was going to be special. A cousin arrived early and said, “I came to get my spot early — don’t let anybody take our spot. Hee hee. Do you need any help?”

Then the second sign arrived in the form of a storm: thunder rolled and lightning flashed all around us. But once we crossed the bridge, the clouds gave way, and the sun began to shine, said another. I said a quiet thank you.

And the rest is the new story we are still writing.

What I Learned About Creative Leadership, With My Family

The last email the night before sounded like this: We are going to have fun and we will have enough. And it was. Here is what I am taking away:

Creative leadership must surprise people. Leaders need to help people see a future they could not see alone. Speak a new future into being. We did this by changing the space, the program, and the menu. It was not without resistance or conflict, but the goal was to gather. We all can grow together when we experience something new together.

There must be opportunities for people to share a new story together while acknowledging old stories. We had an altar where family members brought pictures and artifacts of loved ones. We walked by and saw all the ones who went before us, and acknowledged them in the sunshine. We can honor the past without being imprisoned by it.

All children need reminders that they were made to run free and fly — especially Black children.

And adults need reminders of the innocence of childhood. We asked the adults to bring heritage dishes from their branch. There was fried fish (whiting), crabs (Tidewater, represent), succotash, rice pudding, gingerbread, cabbage. Childhood looked like my sister weeping after tasting the closest approximation of my grandmother’s rice pudding. She said, “I did not think I would ever taste this again. It’s been over 45 years since I’ve tasted this taste,” And her son saying that this was the best thing he had ever tasted in his life. It is legit that good, with or without raisins.

Creative leadership is sensational. When we want people to be their best, we must appeal to their senses in surprising new ways. Bringing the old foods back, and also creating a collaborative menu, welcomed tradition in a new way. We could taste it. Heritage has a taste and a story. The children need to know the tastes of their family. We need to feel something in our bodies in order to move.

Creative leadership also surprises the leader. I wasn’t quite sure what that surprise would feel like or sound like, but I was aware of my hesitation. A few weeks prior, I’d had an accident that left me standing 9.75 toes down. I was keenly aware that I was doing too much — the conditions for success were not in place — and for a 3-1-8 achiever like myself, I do not like losing, or not being able to do my very best. I was calmly overextended, unaware of my own physical exhaustion. All I know is that as we got closer to the day, the exhaustion caught up with me. But I continued anyway. Your leadership should surprise you. That is the edge of the learning curve. That is the edge of growth. There were things that made the day magical that were above my pay grade and out of my control.

I did my best and let the rest go. To have the coolest day in August in Southeastern Virginia with a cross breeze and no humidity or rain surprised all of us.

Sensing Success

In the Western tradition, we have five senses that help us make sense of the world—our sight, hearing, taste, touch, and smell. Creative leadership must appeal to the senses as an indicator for success. We sensed the following low-inference indicators of success:

• The “debts” and “trespasses” were tangled by several traditions and voices.

• “This felt like being at the home place.”

• “This felt like the old days.”

• “We can do this again, easy.”

• “Oooh, we doing crabs today? I smelled them when I pulled up.”

• “Mom! I saw crabs running into their holes on the beach.”

• Or my cousins saying, “This takes me back to my mother’s kitchen.”

The wind blowing and the kite flying. The heritage table with our traditional foods to share. The laughter of children.

In a quiet moment in the hospital the next day, my father asked me what lessons I was taking away from this experience. He, too, was a leader in organizations, a change agent.

I simply replied: how much of an honor it is to be known professionally. But to be fully seen and known by your people — your family, the people who knew you before you fully knew yourself — well, that is an unspeakable joy.

And, when you can lead in your family, trust and believe you can lead any team.

American traditions don’t have to be abandoned, but we do need to let them grow — and trust that we can grow with them too. That’s the work of creative leadership.

We can all fly.

Many were not recognized as the teachers and helpers and were short-lived or misunderstood.

Their stories never made it to your younger generations. We think this because of the break in your membership.

Instruction requires connection. The teacher must stay connected to all of the stories and the virtue of connection to strengthen the membership.

Without it, the young ones may not be able to develop a mature creativity. In our world, because the young ones did not have a holistic understanding of the past, it became difficult for them to make sense of their present.

It is through relationship that the knowledge is transmitted and created.

It is amazing that our young ones remained somewhat creative despite this space in their understanding. I wonder if you see the same pattern in your young people.

Unfortunately, too many delegates and emissaries were seen as threats in your world. They were silenced or exiled. Many of their stories never made their way to the canons of your learning systems. So we must repair that.

On this journey together, I will share the context of many stories so you can see your challenges, obstacles, and problems of practice in their lived experiences.

Connection. Context. Community.

On the journey together you will be able to hear their voices. The archives only collected a part of them, the other parts of them were left as hints and clues about the path that we are on called Radical Inclusion.

These stories are clues.

These stories will also help you see the structure and design of your environment and how they impact children. How they mute. How they rub out creativity. You will see why the children cry and how to respond. You will also see that creativity lives in all of us. That joy is a register of learning.

One more thing. While I can recall much of what we talk about, it might be helpful to keep a journal close by when we are together.

Journeys need journals.

I am sure that you want to meet me face to face. Soon.

Soon we will connect. Very soon.

Join Team Gladys

GLADYS is an AI-powered equity leadership co-pilot built by 228 Accelerator. Learn more at www.wearegladys.com.

This essay is part of The Praxodox: Remaking Ourselves and Our Relationships. Subscribe at equityxdesign.substack.com.

Further reading: “How To Fight: Resistance, Ownership, and Equity” · “A Funeral for the Empathy Interview” · “A Story of American Exceptionalism” — all at equityxdesign.substack.com.

The monsters are back.

This is not a civic failure alone, though its assessment and impact are both public and common. It is not a personnel failure alone — too many people have encountered them. This is a failure of literacy. A failure of education. And because monsters are an education failure, they demand an educated response.

My first name is Caroline. I am the third woman to carry that name on my father’s side. My grandmother and grandfather only finished elementary school because the state of Virginia did not invest in the education of Black people. But my granddaddy got his high school diploma at 55 — because literacy defangs the ignorance that sharpens oppression, and he knew it was never too late to take that weapon back. I am a teacher by calling, an engineer by training, and a writer by choice. My domain is equity-centered leadership — the creative discipline that builds the capacity to redesign relationships and render oppression obsolete.

Monsters live in oppression.

With more than twenty years of teaching children, adults, and teams across America, I have found that defanging oppression requires a battery of literacies — people must have the time, space, and community to interrogate the old ways of the past, observe their emergence in the present, and determine a more creative, novel response. But many adults with great potential for impact are too committed to the traditions of the past, or too consumed by the urgency of the present, to create a transformative future. In that fertile ground of inaction, I play, teach, and lead.

As a practitioner, I’ve observed that because systems of oppression have been designed, they can be redesigned — and we are the designers. This design challenge demands a canvas that is personalized, because our stories are different. It demands creativity on demand, because insight divinely disrespects time. And it demands a framework, because coherence requires structure. The first question: How do we create the conditions for people to co-author their own liberation? We answered it by co-building equityXdesign — a framework for liberatory design practices — as our educated response.

My first name is Caroline. My middle name is Inez. I carry the middle name of my maternal grandmother, Gladys. Her world was governed by segregation and the Racial Integrity Acts in Virginia. Her daughter Annase — my mother — was the first woman in their entire lineage to pursue higher education, not because there was no impulse or instinct. The state did not build the infrastructure. I am a teacher by calling, an engineer by training, and a writer by choice. I studied engineering as an undergraduate and learned to respect mathematics as the language of the natural world — and to understand the ethical cost of extending, accelerating, and automating human hands, feet, sight, and hearing. When it comes to defanging monsters, careful and thoughtful use of technology to extend the brain’s creative capacity must respect the relationship between humans and their environment, between human beings, and between humans and their future selves.

Especially now — when equity work, branded DEI, is cast as anti-American and laden with shame. The work most needed for our collective evolution is experienced as painful and uncomfortable for the powerful. We have to build this literacy and make it worth returning to. We need to make equity work irresistible. The second question: How might we use technology to extend human capabilities and scale equity in schools and communities — in a way that respects what is essentially human — and make that experience irresistible?

We built GLADYS.

GLADYS is an AI-powered equity leadership coach — a school leader’s partner in creativity, grounded in equityXdesign and built on Fugitive Data Architecture principles that keep educator data sovereign and protected. GLADYS does not replace the human. She extends it — toward justice. She meets leaders in the exact tension between who they are and who their students need them to be. Built by and for those most excluded from the rooms where these technologies are designed, GLADYS is currently entering her founding cohort, partnering with equity leaders across the country to scale what accountability alone never could. You can find her at www.wearegladys.com.

My first name is Caroline. My middle name is Inez. My last name is Hill. I am a teacher by calling, an engineer by training, and a writer by choice. I write for those denied the opportunity to learn to communicate with the written word — to understand it, and use it to build a world without boundaries or margins. I write for my younger self, whose heart came more alive finding Audre Lorde, bell hooks, and Pat Parker — writers who taught me how to stand in the tradition of the Black woman who refuses a world that releases monsters too readily. I write to say I was here. I matter. And I hope to inspire others to know their ideas matter too.

My deepest question remains: How do I write so that engineers see themselves in the teacher, and teachers see themselves in the engineer, and each of them sees their own mark on the human story? How might I write to bring difference together without division?

This writer, teacher, and engineer co-built an AI-powered learning experience with educators — especially the most marginalized and excluded. This where that question finds its sharpest edge — a community of practitioners committed to technology that heals rather than extracts, restores rather than surveils, and builds power rather than consolidates it. That is the work. That is why I am here.

Monsters get back. Get way back.

I know you hear them too, or at least you know of them; that is why you are here. That is why you do the work that you do. You can no longer tolerate the suffering.

I’ve come in the form of the silenced, the muted, the ignored, and the disrespected. This is the form that can bring this message to you, and in a way that will facilitate the most creativity.

In this form, the creative ones see me as someone who can help. Only in this form is the true function of my arrival revealed.

Just like in your world right now, some did not want to change, to tune in, and create. There were those who chose not to see. There were those who could no longer hear. Then, there were still some who could see and hear and had the power to create and chose not to.

They would explain their reasoning confidently. They could explain without deep listening. It always made sense to them in the way they made sense of their world. They tried to progress without vision. But unfortunately often just repeated the past. Change was hard for them.

But from afar, we could see why. The anticipated shock to their nervous systems was thought to be so great that change was abandoned before it even started. Even though they were strong enough, they did not think so. Many wanted change but did not want to lose anything. Accumulation was such a practice that too many lost the ability to discern that not all loss is bad. Loss can make room for something new. They suffered unnecessarily in their own accumulation.

Because they were so disconnected from the rest of the membership, they were too far to tune in. The signals and impulses were still present, but they took too long to respond. Over time, the membership broke. Some were cut off and forgotten. Those faraway bits no longer spoke to them. They forgot themselves.

I’ve come because I have seen this pattern before. I think you see it as well. Our worlds are not so different. My world has been where you are. We know there is a different way. I have traveled this journey before and know that change is possible. But the way forward will require courage, community, and most importantly, creativity.

The way forward is Radical Inclusion. We must design it together.

On this journey, our goal is simple—stay connected and create more creative ones. Unleash your own creativity and inspire others in the membership to do the same. We will practice hearing the silenced. We will amplify the muted. We will respect the disrespected. We will put the membership back together. We will design the path forward.

This is a little bit about where I come from. I’m excited to journey with you.

GLADYS is an AI-powered equity leadership co-pilot built by 228 Accelerator. Learn more at www.wearegladys.com.

This essay is part of The Praxodox: Remaking Ourselves and Our Relationships. Subscribe at equityxdesign.substack.com.

Further reading: “How To Fight: Resistance, Ownership, and Equity” · “A Funeral for the Empathy Interview” · “A Story of American Exceptionalism” — all at equityxdesign.substack.com.

It also sounds like the same story.

While there is an individual role in creativity, more often than not, the insight and impulse wither quickly without the infrastructure of the people.

Individuals may have insight. But people are creativity infrastructure.

Newly freed Black Americans long had the impulse for their own liberation and freedom. Rebellions were common. Literacy was freedom. But it was the infrastructure of the collective–coordination, cooperation, and collaboration that spread the message of emancipation. To depend on the planter to carry the message of freedom was to live and die enslaved.

Liberation was not the business of the minority of Americans at the time, just the opposite. It did not need the megaphone of planter class. It would never have it. The business owners needed enslaved labor to support their lifestyles. But the majority of Americans were busy, at something more creative—dismantling the entire system of the Southern slave economy without violence.

DuBois reminds how non-violent withdrawal constricted the violence of slavery :

It must be borne in mind that nine-tenths of the four million Black slaves could neither read nor write, and that the overwhelming majority of them were isolated on country plantations. Any mass movement under such circumstances must materialize slowly and painfully. What the Negro did was to wait, look and listen and try to see where his interest lay. There was no use in seeking refuge in an army which was not an army of freedom; and there was no sense in revolting against armed masters who were conquering the world. As soon, however, as it became clear that the Union armies would not or could not return fugitive slaves, and that the masters with all their fume and fury were uncertain of victory, the slave entered upon a general strike against slavery by the same methods that he had used during the period of the fugitive slave. He ran away to the first place of safety and offered his services to the Federal Army. So that in this way it was really true that he served his former master and served the emancipating army; and it was also true that this withdrawal and bestowal of his labor decided the war. - Black Reconstruction, WEB DuBois.

The liberation of the people needed the people. It was the myceliated masses breathing together, heaving together, laboring together until the conditions were ripe for creation. This is the work of a new story.

These are leadership lessons that we can all learn from. The real work of leading is learning to use your body—what you see, hear, say—to coordinate, connect, and collect other bodies and learn coherent movement together. Leaders stay ready so that they do not have to get ready. Leaders also make sure that the people get ready too. They move together.

This is creativity because it requires assessing the present and creating something new that is just for that moment. Not something for yesterday. The dead past is unchanged and the fertile future is yet to come. Creativity is the living response for now.

So as we acknowledge the liberation of the people, our job is to stay connected, look, listen, and move together. The labor of creation will do the rest. What a special story!

Stay connected. Stay maladjusted.
Caroline

Gladys: Leadership Infrastructure for Creativity

It never fails that a teacher or leader in a learning session says something like, “The system is doing exactly what it was designed to do.” Everyone nods in agreement, as though recognition alone is enough. But structural literacy—the ability to see systems and understand their impact on people—is both necessary and insufficient for equity-centered leaders. Once we see the system and name the harm it causes, we must do more than acknowledge it: we have to build a better response. Different results require different systems.

So we need infrastructure and learning that can scale, helping us create and design better responses. We need to connect creativity to building whole systems, not propping up broken ones. That is one reason we are building Gladys. But we know that creativity is not a solo act. We want to build with leaders, principals, and teachers.

If you want to learn more about the pilot, what we are building, or if you are ready to sign up, register and I will follow up with you directly. Of course, if you have any questions, DM me directly. Let’s build this together!

Join Team Gladys

I’m keeping this newsletter shorter because we’re taking a brief break. We’re using this time to write about our process of building Gladys, prepare for the pilot, and spend time with family. Look out for the Juneteenth piece on Friday

We also want to capture and codify everything we’ve learned this year as we get ready for the next edition of The Praxodox and The Untrained Model.

Share The Praxodox: Remaking Ourselves and Our Relationships

Here's where that question leads us next.

If we are building a tool to help equity leaders imagine their way into what doesn't yet exist — a real co-pilot, not a chatbot, not a search engine — then we have to ask: what does that tool sound like? Because GLADYS is only as good as the relationship she can actually build. And the relationship starts before the first idea lands.

It starts the moment someone hears a voice and decides, in the body, whether they are safe.

Voice is not neutral. It never has been. The sound of authority has always been raced, gendered, classed, credentialed. We've been trained since birth to hear competence in certain cadences and confusion in others. Safety in certain tones and threat in others.

As designers, we must hold these questions: How does our lived experience change our sound? How does grief sit in the larynx? Where do the vocal cords hold restoration and repair? What does possibility and promise sound like? And whose bodies have the resume’ to hold it?

In other words, what wavelength does the future hum on, and how do we all learn to pick it up? As we move closer to making choices about how to ethically shape these experiences, we need your perspective.

Listen to these voices and tell us what resonates with you.

We're going deep on what GLADYS sounds like — and what that means for the leaders she's designed to serve. We're talking voice cloning ethics, the equity implications of AI authority, and what it actually feels like when a tool speaks to you in a voice that was built to close the distance.

Impact starts in the ear. Can you dig it?

Stay Creative and Maladjusted,

Caroline

GLADYS and the Environment: Why This Matters Here

The concerns are real. Data centers consume enormous amounts of energy. Most of that energy comes from fossil fuels. And the communities bearing the heaviest pollution burden from those fuel sources — the ones living closest to the power plants, the cooling towers, the infrastructure — are disproportionately communities of color. That is not a coincidence. That is a pattern.

So when we say GLADYS is an equity tool, we mean all the way down.

Here's how to think about the environmental footprint of any AI system: three questions. Where is the data center located — and who lives nearby? What powers it — renewable sources like solar, wind, or hydroelectric, or fossil fuels? And how large is the server — because size determines how much energy is consumed at every query.

GLADYS runs on a private server powered by hydroelectric energy. That means the electricity moving through every interaction with GLADYS comes from water, not coal. No combustion. No carbon-heavy grid dependency. No emissions exported into someone's neighborhood.

And because GLADYS runs on a small, purpose-built private server rather than a massive commercial data center, the footprint is minimal by design. This is what our environmental impact white paper calls the lowest-emissions tier — API-first architecture, right-sized infrastructure, and a clean power source.

This is not greenwashing. It is a design commitment that matches the mission.

An equity co-pilot that harms the environment — that draws power from systems that already extract from vulnerable communities — would be a contradiction we cannot afford. GLADYS was built to close distances, not create new ones.

The power source is intentional. The infrastructure is intentional. The ethics run all the way to the outlet.

If you want to know more about what that is, why it is important and how understanding this design can help you make more informed decisions, join the Gladys pilot.

Join Team Gladys!

Pausing for July. Restarting in August.

July belongs to life.

We’re pausing the newsletter for a month—not vanishing, but deliberately choosing presence over publishing. GLADYS pilot invitations stay open through the end of the month, and the work required to get there is exactly the kind that can’t be hurried: cultivating relationships, welcoming new leaders, and ensuring the human infrastructure is as sturdy and intentional as the technical one.

We’ll drop a note here and there when something can’t wait. But mostly we’ll be in rooms, in conversations, in the slow and necessary work of getting ready.

We’ll be back in August — fully, loudly — when the GLADYS pilot launches, and we start learning in public.

What the technology does. What we do with it. What it surfaces about ourselves and each other.

That’s the newsletter worth writing. The countdown begins…

He said: You don’t have to tell the story we’ve been listening to. You can tell the story we need to hear.

We were talking about data and logic models. About GLADYS. About the overwhelming evidence of need — and the harder question underneath it: how do we define effectiveness?

I went back to the drawing board. Not disappointed. Not ashamed. Just reminded of how hard it is to be creative. Because our measurement often becomes the story that repeats. How do we tell a new story?

And then it came: creativity is the thing. Not better compliance. Not faster execution of old ideas. Creativity. Leaders with the courage to turn left when everyone is going right. Leaders who refuse to be silent. Leaders who know we have to make a way out of no way — and who understand that the knowledge needed to transform our schools may not yet exist in any book, any dataset, any framework we currently hold.

We have research. We know what to do. But knowing how that knowledge lives in the body, how it sits on the tongue, how it moves through the hands — that knowing is still emerging. That knowing runs on imagination and emerges in practice.

Khalil Gibran Muhammad offered us a lens: in an instant, historically speaking, four million people shifted from being treated as property to being recognized as human beings and then as would‑be citizens. What once seemed impossible became reality. Yet most white Americans did not transform at the same pace, and this stagnation of imagination — this failure of creative vision — was embedded into law and baked into what we measure and evaluate.

So here is the design challenge. Instead of measuring achievement gaps — a metric that installs white performance as the ceiling and the standard — what if we tracked creativity? What if we measured how alive our leaders are to possibility? How do you measure that? I don’t know yet. That’s the point. That’s the work.

Maybe we stop repeating old solutions to old problems. Maybe we come at the same problems from a completely different angle — one that pulls all of us all into the mystery, the unknown, the new territory of creation. Where no one already has the answer. Everyone has part of the answer. Where the contribution is equal because the problem is genuinely unsolved.

That’s the story we need to hear. That’s the story that we need to write.

Stay Creative and Stay Maladjusted,

Caroline

(It’s Malcolm X’s birthday, y’all, and we have a treat for you!)

Free Equity Work: Malcolm X - The Ballot or the Bullet

“We don’t see any American dream. We’ve experienced only the American nightmare. We haven’t benefited from America’s democracy. We’ve only suffered from America’s hypocrisy.”

Every May 19th, we pause.

Not to perform. Not to post. To actually read.

Malcolm X’s “The Ballot or the Bullet” — delivered in 1964 — is one of the most precise diagnoses of institutional power ever spoken aloud in America. In it, he makes an argument that equity leaders are still having to make today: that political and economic self-determination are not separate from the work of justice. They are the work.

He draws a line between personal faith and collective strategy. Between sentiment and structure. Between the language of civil rights — which asks the powerful for permission — and the language of human rights, which doesn’t.

That distinction lives inside everything we build at 228 Accelerator.

This month’s Free Equity Work resource is the full speech — paired with historical context and three reflection questions for your team or your own practice.

It’s an invitation to sit with the kind of clarity that doesn’t make institutions comfortable. Which is, of course, exactly why we still need it.

Happy birthday, Brother Malcolm.

This is about human rights.

“Once you change your philosophy, you change your thought pattern. Once you change your thought pattern, you change your attitude.

Once you change your attitude, it changes your behavior pattern, and then you go on into some action.”

GLADYS Pilot: AI Literacy + Equity Leadership? Yes!

Most AI professional development asks you to learn a tool. This asks something harder.

The GLADYS Pilot Learning Plan is a six-month curriculum designed for equity leaders who want to develop real AI literacy — not the kind that teaches you to prompt better, but the kind that asks: what is this tool actually doing, who benefits from it, and what does it reveal about you?

Across six months, leaders move through the equityXdesign 3.0 curriculum while running five simultaneous investigations. Three track the AI co-pilot — what personalization looks like, whether it serves the mission, and what it costs to show up with this technology inside equity work. Two track something the field rarely names: the conditions that creative leadership requires, and where that creative energy goes when the institution pushes back.

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The reading is all free. It runs from Timnit Gebru’s suppressed AI ethics paper to Black Reconstruction to somatic practice. Every text earns its place.

By Month 6, each leader has a data story — six months of evidence about their own proximity, language, and creative capacity. That is what AI literacy looks like when equity is the frame.

Gladys. Accelerating the human relationships that change something significant.

Change Something Significant

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In this speech, Malcolm X outlines his political, economic, and social philosophy of Black Nationalism. He argues that Black Americans must control the politics, politicians, and economy within their own communities rather than relying on a white-dominated system. He urges Black citizens to stop spending their money outside their communities, which only makes other communities richer while turning their own neighborhoods into impoverished slums. Instead, he advocates for a “self-help” and “do-it-yourself” philosophy, encouraging the creation and support of Black-owned businesses to generate local employment.

A major theme of the speech is the failure and hypocrisy of the United States government and the two-party political system. Malcolm X argues that politicians—particularly Democrats, who rely on the Black vote to win elections—have consistently failed to deliver on their promises and are often allied with Southern segregationists (whom he calls “Dixiecrats”). He characterizes America not as a democracy, but as a colonial power, stating that “second-class citizenship” is merely a modern form of slavery.

Because of this government failure, Malcolm X advocates for elevating the struggle from civil rights to human rights. He argues that fighting for civil rights keeps the issue under the jurisdiction of the U.S. government—the very entity responsible for the oppression. By reframing it as a human rights issue, Black Americans can take their case to the United Nations and accuse the U.S. of violating human rights, similar to how international cases against South Africa or colonial powers were handled.

Finally, he warns that a new, frustrated generation of Black Americans is no longer willing to wait for gradual change and is prepared to demand “liberty or death”. The choice facing the country, therefore, is between giving Black people their full rights through the voting booth (”the ballot”) or facing a violent revolution (”the bullet”). To achieve these goals, he stresses the absolute necessity of unity, urging Black Americans to put aside their religious differences and work together against a common enemy.

As long as you fight...

Discussion Questions for Leaders and Teachers

1. The Philosophy of Black Nationalism How does Malcolm X define the political and economic goals of Black Nationalism? What are the consequences, according to the speech, of Black citizens spending their money outside of their own communities, and what is the proposed solution?

2. Civil Rights vs. Human Rights Why does Malcolm X argue that the struggle must be expanded from the level of “civil rights” to “human rights”? What is the strategic advantage of taking the Black American struggle to the United Nations, and how does this reframe the U.S. government’s role in the conflict?

3. Political Critique and Voting Power How does Malcolm X view the relationship between the Democratic Party and “Dixiecrats,” and why does he refer to Black voters who blindly support the party as “political chumps”? In what ways does he suggest the Black vote can be used as a “key factor” or strategic bloc in closely contested elections?

4. The Analogy of Colonialism Malcolm X compares the condition of Black Americans to colonized people in Asia and Africa. How does this comparison help explain his prediction of “the ballot or the bullet”? He mentions that the founding of the United States was based on a violent rejection of “taxation without representation”. How does he use the figures of Patrick Henry and George Washington to justify the impatience of the “new generation” of Black youth?

5. Unity and Religion Why does Malcolm X, a devout Muslim, insist that religion should be kept “in the closet” and out of the political struggle? How does he differentiate between the goal (freedom) and the methods (integration vs. separation), and how does he propose overcoming the “divide and conquer” tactics used against the Black community?

At least it looks that way from where we’re standing or sitting.

One day, everything is what it has always been. The story itself becomes the table of our experience — solid, familiar, assumed. Our lives rest on it. We don’t notice it. We just live on top of it.

Then the event happens.

And when the event is significant, the story we thought we knew changes. Our current knowledge becomes obsolete. We don’t know how to move forward. The knowledge we need hasn’t been created yet. It isn’t even conscious. It’s waiting — on the other side of something we haven’t survived yet.

Significant changes shake the table.

When the table shakes, impostors become irrelevant. So does being the exception. The performance falls away. What’s left is just you, and what you actually know, and whether it’s enough. This loss — of the story, of the role, of the self you built on top of a table that no longer holds — is grief.

As a family, we have experienced some significant table-shaking events. Death has quaked our table. So have extraordinary acts of public kindness and generosity we did not see coming. Each time, when we chose — courageously, imperfectly — to stay together, we all stepped back and took on new roles to keep things as stable as possible. We tried on new seats. We shored up our footing in the unfamiliar.

And in those new seats, in those new roles, something unexpected happened.

We could see differently.

What can I see from this new seat that I could not see before? Who can now see what I couldn’t — or chose not to? Maybe it was the table itself that was shaping not just what I saw, but how I saw. Changing my sense of knowing. Changing me.

We were re-created.

This is the paradox. We cannot create new knowledge from the same seat. We cannot create new knowledge playing the same role. And yet we resist the unfamiliarity that new knowledge requires. We want comfort. We want creativity. We don’t fully reckon with the fact that they are incompatible.

Significant change is a creative force. It requires discomfort. Sometimes pain. Pain and discomfort are the price of new knowledge — not a sign that something has gone wrong, but the labor of something being born.

When we can manage to stay together in the pain — in the duty, in the labor — we can all be changed. Hopefully for the better. We may even arrive at something more surprising than a new story.

We may realize we don’t need a table at all.

Good grief.

Stay Maladjusted. Stay Creative.

Caroline

Create the Knowledge That Changes Everything: Join the Gladys Pilot

We are losing our most creative leaders at exactly the moment we need them most.

Not because of bad people. Because of exhausting systems. Systems designed for a narrow population that burns through the creative capacity of everyone trying to serve a broader one. The departure comes later. The depletion comes first — and it comes quietly, invisibly, in the daily grind of leading inside institutions that were never built for the work you are actually trying to do.

Gladys makes that depletion visible before it becomes departure.

What Gladys Is

For five months, Gladys sits in your pocket as an AI creativity and equity partner — helping your organization’s leaders imagine new possibilities, navigate ambiguity, and turn daily practice and monthly peer feedback into bolder, more creative decisions.

Not a chatbot.

A creative thought partner grounded in culturally responsive practice and the real, unscripted challenges of leadership today. Gladys is built for the moments between the meetings — when you need to think something through, when the path forward isn’t clear, when the data says one thing and your instincts say another. Plus, you can also learn to be a leader in the AI era.

Leading through uncertainty demands creativity. Gladys accelerates it. When you work with Gladys, you are not just developing as a leader. You are co-designing the knowledge your organization needs to move differently.

If you are a school or system leader ready to build something real — to develop your creative leadership practice inside a community that takes the work seriously — Gladys is your co-pilot.

Applications open now. Cohort begins August 2026.

Gladys. Accelerating the human relationships that change something significant.

Change Something Significant

Black Reconstruction, the Voting Rights Act, and the Control of Labor

The Supreme Court’s recent decision in Louisiana v. Callais was a table-shaker.

And we could all become the shook ones — not just Black folk, but the entire Public Body.

Let’s sit with the public discourse for a moment. Media outlets reached for the word eviscerate — to disembowel, or more informally, to gut. I understand the instinct. But I don’t think this decision is gutting. I think it’s worse.

It’s bone-breaking.

In a democratic republic, the vote is the skeleton of the people. Economic agency is the muscle. You need both for movement. A gutting is devastating — but you can still stand. Break the bones, and the body cannot hold itself upright. The muscle has nothing to attach to. There is no movement.

That is what is at stake here.

But we are students of American history. And students of American history know how to follow the pattern.

This decision lives in the same lineage as the organized, extrajudicial, violent terror that swept the South after the Black governments gained control of governance during Reconstruction. That chapter of history is not told often enough, and it needs to be told plainly: in the Southern states, the freed Black majority held the right to vote. They reformed government so that it worked for the working class — in both creed and deed. They built something real. Something that served people who had never been served before. There was no violent revenge…

And the response was not a debate. It was not legislation. It was not a court case.

It was terror. Organized, systematic, and deliberate. Designed not just to remove Black people from power but to break the bones of a democratic experiment that was beginning to work — precisely because it was beginning to work for everyone.

Callais is not identical to that moment. But it is in the same lineage. The same reflex. The same recognition that when the voice of the people is structured in ways that threaten concentrated power, that structure must be dismantled — not because it has failed, but because it is succeeding.

The table has been shaken before. It was shaken by design.

The question — the one history keeps asking us — is whether the Public Body will stay together in the shaking. Whether we will step into new seats, take on new roles, and refuse to let the bones stay broken.

Democracy is not a table. It is a body. And bodies, even broken ones, have memory. They know how to heal. But only if we stay in the labor together. The table is going to shake for a long time, unfortunately.

But even in the shaking, we know that these children will not sit in the back of the bus, and no one is going back in the closet. We have created more knowledge to live out loud.

Follow the Chapter: XIII. The Duel for Labor Control on the Border and Frontier on Substack notes to see the pattern.

There are crumbs everywhere.

Lit — What We’re Reading and Writing This Season

We are working on a few essay-articles about teacher feedback, thinking, being, and leading differently. In the meantime, sweeten your tea with this sugar…

“Perfection in colonial thought systems, conquest habits, and separation efficiencies only direct our agency toward violence, trauma, and distress. We get good at that type of thinking, and those habits are acknowledged for it. This recognition comes at a high cost. If supremacy and its thought routines have been the tradition and culture for the past 1000 years, the new democracy and its ways of thinking and thought routines are the counterculture needed for balance and to right the relationship. “

My family has a way of dealing with ghosts, haunts, and spirits. We have our blessings, our rituals, and incantations. We have our candles, sage, and salts. There is respect for the spirit world and the discernment of intent for those beings that are no longer bodied. When an unwelcomed spirit would visit, there would be much discussion on its message and purpose, finding ways to create distance when needed or desired closeness for comfort for the grieving.

Ture argues that participation (like voting or schooling) only matters if it builds collective power. Where in education today do we mistake access or participation for real influence—and what would it look like to redesign for actual agency?

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As a reminder, supremacy exists when there is first fragmentation or separation in ways of thinking, and then a particular way of thinking, or a singular thought process, is elevated as worthy. Without separation, the thinking and ideas remain interdependent, linked, and bound together. If we are to exist together as one unified whole—a healed self, a healed environment, and a healed relationship with other living beings, humans included—we not only need to interrogate our thinking and its impact on our actions and relationships, but also prepare ourselves for a wiser response. The notion of a ‘wiser response’ is not solely restricted to the words and sounds we make, although they may be important. This is especially true as DEI initiatives and executives are actively being sidelined, and the rights of the poor, women, and the LGBTQIA+ communities are being shocked back into the perverse fantasies of the oppressor.

The wiser response lies within what we build, what we design, and what we scale.

• What do we create?

• How do we create?

• What do we prepare?

• What do we test?

And how do we know that our ideas are oriented towards healing ourselves and our collective consciousness, and towards getting us closer to this daily, deliberate, democratic practice of integration?

• How creative are we willing to be?

• And what is in our way?

These are the questions we must ask to begin this work.

The Paradox of Perfectionism and Creativity

Tema Okun’s widely circulated resource, White Supremacy Culture, offers that one of the first characteristics of white supremacy culture is perfectionism—the idea that mistakes are not allowed and that there is only one way of completing tasks. Perfectionism is often pedestaled as it can foster a professional climate of competition and achievement. Advocates argue that without perfection, a climate of low-quality work products abounds, compromising productivity and professional standards. But when designing and bringing forth the work of the multiracial, multicultural, multilingual democracy, we need to take a closer look at perfectionism, how it operates to create the context for supremacy, and how it strangles creativity.

For a closer look, this thought experiment may help:

Imagine you have been on the Moon, looking at Earth, for 1000 years. Suppose you watched the past 500 years through a particular lens of thinking and thought processes. In that case, you might notice how efficiently and effectively European thinking has conquered the Earth’s people through colonialism and industrialization. Jared Diamond would remind us that it was not only the guns, germs, and steel that conquered other lands—ideas were conquered too. While we will not discuss or argue the quality of these ideas for the sake of this thought experiment, each time there was a clash of cultures, one thought system prevailed by either conversion—using violence to make others think like them—or annihilation. If we are one unified whole, then all of the world’s people have ways of thinking and making sense of the world that contribute to that whole. When those ways of thinking are unavailable, our collective consciousness is imbalanced. It is as if we are still trying to create, elevate, uplift, and build with an incomplete toolkit. Our designs suffer, and we suffer. Perfection in colonial thought systems, conquest habits, and separation efficiencies only direct our agency toward violence, trauma, and distress. We get good at that type of thinking, and those habits are acknowledged for it. This recognition comes at a high cost.

If supremacy and its thought routines have been the tradition and culture for the past 1000 years, the new democracy and its ways of thinking and thought routines are the counterculture needed for balance and to right the relationship. The new democracy may be supremacy’s much-needed, right-sizing complement. But getting there and practicing this daily will be difficult.

First, tradition values and celebrates the past. Tradition creates spaces of belonging. Tradition is familiar with its blueprints and plans. Creativity breaks tradition and requires a different way of thinking and being. It recognizes the current dominant patterns of thought and makes the conscious choice to change direction. Rarely are radically different ideas socialized. Rarer still is the socialization of the humans who steward the radical ideas. Instead, we marginalize and terrorize those who dare to offer a different way of thinking or being. Think about the queer child in the family who stays in the closet for years. Or the interracial relationship that is isolated from both families. Tradition teaches us to be flexible within bounds. It teaches us to stay within the lines.

However, when we apply a lens of creativity, healing, and wholeness in a world of separation, it becomes apparent that a new thought pattern and thought routine are required. Too often, we perceive highly skilled people as creative people simply because they are fluent in dominant thinking and thought habits. And while these skills are essential, they alone do not incentivize creativity or change thoughts and patterns. Sometimes, having more skills incentivizes and cements tradition.

A true quest for creativity guides us to the edges of society. Different thinkers live here. The margins shelter humans who live in ways that challenge the storms of convention and tradition. They create new ways of being, new ways of relationships, and new languages to hold and share their experience. The margins root the humans whose skin holds the sun, creating spaces to critique the shade of dominance and oppression. The margins leave both the apex and the blade that bend and move in a multitude of forms as they give shape to the wind. They hold the space for those who have decided to come to live on their terms, creating new spaces of inspiration, freedom, and belonging. But this freedom in a traditional world comes at a cost. Too often, humans pay the price of their creativity in blood in traditional worlds.

But this kind of free and permissionless thinking, or at least its spirit, is necessary to balance supremacy and build a multiracial, multicultural, multilingual democracy. The genius at the edges reminds us that the diversity of thought and body can give us the best approximations of our equitable designs.

When we lean into ways of being that mirror the past, perfection as a condition and state becomes the safety belt that straps us in, keeps us stable, and gives us a feeling of invincibility. It changes our relationships with each other from companions to competitors. For those fluent in the tradition, it creates a power dynamic that fuels a one-way ticket to the past— perfectionism becomes the supremacy’s perfect travel companion. We have to become perfect in unpracticed ways, not for the sake of progress but for balance. This is hard when the dominant thought system is so rigid that it cannot absorb the threat of difference; instead, it is rejected. Enabled by the thinking of the past but moved by the body in the present.

But when we enter new relationships where body supremacy does not exist, we must create new knowledge, ideas, and insights. We need new racial knowledge. We need new cultural knowledge. We need another way. We may even need new words and a new language to express ourselves. Our old ideas become obsolete.

We would need each other differently, knowing that the blueprint, the new tradition, and the new way require meaningful contributions from all of us—our thoughts, actions, experiences, and ways of being. The state of perfection becomes obsolete—as a living process, we collectively live, design, and build together.

The paradox of perfection lives in the human need to belong and be seen. We desire creativity but rarely lean into the experience of our own marginalization for wisdom or stay close enough to the suffering at the bleeding edge to let it transform us. We love the nostalgia of tradition, the community it creates, and the perfection and recognition it inspires. We also know this tradition, sense of belonging, and perfection may inhibit our creativity. To ease the tension, we may elevate one at the expense of the other, rather than finding a new relationship that can hold both in an interdependent manner. This is the tension and the paradox that we must hold.

How about we create a healthy relationship between perfectionism and creativity?

How might a design stance guide us on this journey?

Prototyping the Multiracial, Multicultural, Multilingual Democracy as Deliberate Practice

To prototype this new lifestyle, it is not only necessary to change our thinking; we have to intentionally put our bodies in new and different spaces to allow our thinking to change. This is why co-design, co-creation, and collaboration with the expertise at the margins are essential design practices of the new democracy.

Our thinking, assumptions, and beliefs are made visible in our relationships. We can see them. We can feel them. Other people can help us hear them. This will feel unfamiliar. This dissonance challenges perfectionism. There is no traditional blueprint for assessment or judgment when doing something new. We are guided as friends, companions, and collaborators, not competitors.

Changing our bodies without changing our programming will result in the same output. But when the practice of transformative empathy elevates the expertise of those living at the margins, it also lifts up the thinking of the margins. When we determine ways to unify collective thinking, uniting both in different ways, we create space for a new direction.

Democracy welcomes learning. The multiracial, multicultural, multilingual democracy will require new learning for all of us. Learning requires us to see each other as fully human with unique stories, gifts, and insights to contribute to the whole. It may sound like I don’t know, but we can figure it out together.

Learning sounds like specific feedback, assessing, and rewarding brilliant mistakes to balance our incessant traditional need for perfection. It could be acknowledging the wired and analog technologies designed to unify our collective consciousness to balance our fragmentation. We synthesize and bring ideas and people together to still our restless need to analyze, separate, and differentiate. It could be why we struggle and stress to do things the right way, and the real lesson is learning how to relax into the struggle, be still, and breathe. Our assessment becomes more about being balanced than being perfect. Our assessments look for alignment and fluency. We value stillness in movement.

But before we engage in the practice to unify the collective consciousness, we must attend to the individual consciousness. Alignment may sound overwhelming, but we can start by assessing our private and public selves and ensuring they are in harmony.

• Do we show up as the same person in public and private spaces?

• Are we living in ways that create new and different relationships with the most marginalized and excluded to open up spaces for creativity?

• Are we organizing and aligning our time and resources to create new racial and cultural knowledge?

• Are we always trying to keep our focus on alignment and balance, correcting and healing ourselves first?

The multiracial, multicultural, multilingual democracy as deliberate practice starts with us. Realizing and aligning ourselves first in our power to emerge as creative beings freed from tradition, far from perfect, but more balanced and aligned every day, is the prototype and building blocks we all need to unify and heal our collective consciousness.

Democracy can be taught as deliberate practice. It is the conscious and intentional act of our words, stories, and actions. It exists within and beyond the franchise and cannot be contained or fragmented into two, four, or six-year intervals. It is what we do every day. Democracy is a lifestyle.

Getting Started Anyway: Building the Multiracial, Multicultural, Multilingual Democracy

As we acknowledge that deliberate practice starts with us, we can each embrace ideas and practices to help us begin this work. In that spirit, these are five design challenges for equity-centered designers to embody the multiracial, multicultural, multilingual democracy as a lifestyle starting in the here and now.

Challenge Perfectionism: Designers need to challenge the culture of perfectionism, which can stifle creativity and innovation. Create environments that embrace mistakes as opportunities for learning and growth, and foster the understanding that there may be multiple valid approaches to solving a problem rather than just one ‘perfect’ solution. This could create assessments that value mistakes as learning.

Codesign at the Margins: Actively involve people from marginalized communities and embrace their expertise in the co-design process. This challenge involves breaking away from traditional thought patterns that may have been influenced by supremacy and embracing diversity in thought and experience as essential to equitable design. This could include stories of marginalization and exclusion to balance the dominant narratives.

Cultivate Transformative Empathy: Challenge designers to practice transformative empathy by understanding and elevating marginalized communities' perspectives. This involves recognizing the value of different ways of thinking and integrating these insights into the design process to achieve more inclusive and innovative solutions. This could look like regular meetings with the most marginalized students and families, and redesigning your professional work to support their success.

Reevaluate Classroom and Boardroom Traditions: Equity-centered designers should critically examine traditional values and practices ingrained in design culture, and how they may perpetuate supremacy. Creativity requires breaking away from tradition and adopting different ways of thinking. The challenge lies in promoting creativity without alienating those who value tradition and in harmonizing both to foster innovation. This could be reevaluating grading practices, assessment design, and student grouping rituals.

Integrate Equitable Tools and Frameworks into Instructional Design: Develop tools and frameworks that promote inclusivity and diversity in the design of instructional experiences. This includes reassessing existing methodologies and technologies to ensure they do not perpetuate supremacy or exclusion and creating new ones that are inclusive and responsive to the needs of a multiracial, multicultural, and multilingual society. This could look like determining standards of learning that support equity literacies as leadership competencies.

Equity-centered designers challenge supremacy at each stage of the design journey. Not just racial supremacy, but all types of body supremacy. Challenging supremacy in action means loosening our grips on the past just enough to allow us to inspect, interrogate, and make space for new ways of thinking and being. This first starts with the designer.

Most of us define perfection as being free of flaws and defects. That is impossible. But in our world designed by oppressive social hierarchies, our thought routines and, thus, our relationships with other humans have been designed to see those at the bottom of the hierarchies as flawed and defective. This tradition has a tight grip on our imaginations and creativity. The imbalance itself threatens our perfection. Our creativity is needed for balance—a place where the wisdom from the margins and the knowledge of tradition can be held together without submission or elevation. This creative endeavor is worthy of our attention, energy, and pursuit.

Perhaps this is the only practice worthy of perfection.

There is an idea buried deep in the American identity. It goes by the name of American exceptionalism. On the surface, it sounds simple — we are the best country in the world. Beneath that, it is something more fixed: the inherent belief that the United States is uniquely and fundamentally superior to other nations — not by chance, but because of our institutions and the well-marketed mythology of individual liberty and democracy.

This belief — and ultimately, this posture, this way of being — is an artificial but powerful cocktail: dopamine and serotonin. A rhythmic pulse in our cultural bloodstream, intravenously dripped through our education, our media, our shared portals of knowledge transmission. It justifies our relationships abroad while requiring no reciprocal attention to those at home. It makes us feel good without critique. Directs our gaze outward, never inward. Expand, exploit, and colonize rather than interrogate, introspect, and commune. Rather than heal our corporate nervous system, the narcotic numbs the wounds. We fester in the repetition of mythology.

Don’t worry — this is not an America-bashing piece. Given the times, that would be too easy. Cheap, even. Unworthy of intellectual rigor. Too many of us live the distance between virtue and vice. Instead, I offer another way to think about American exceptionalism.

Last week, I returned to my undergraduate institution—The University of Virginia—to celebrate Black Alumni Weekend. It was only in the year of my birth, 1977, that UVa enrolled more than 500 Black students, laying the foundation for a community of academic trailblazers, institutional builders, and true exceptions in the American story—a story about how to be together as equals in the classroom, cafeteria, and in the commons. UVa’s story was changing. I joined that changing story in 1995.

Together, we wrote a different, exceptional American story. It was not always easy. Much of it was never recorded. So thankful for that. It was not always fun. It was, however, the next chapter of American democracy in practice—claiming roles and earning wages befitting of our intellect and humanity, practicing the rhetoric and communication for public advocacy, and refining the technical skills necessary for imagination and design. And experiencing the people and relishing in the friendships that dispel toxic mythologies.

Democracy is healing when we let it live.

To find our footing in a strange land, the same one our parents, grandparents, and great-grandparents navigated by the very stars we were wished upon. The diploma offered a kind of safer passage and a turbo-charged jetpack. It has all served me well.

My friends — Class of 1999 — sat around Central Grounds and witnessed our own growth—laughing, smiling, tearing and tearing, exhaling into a space that did not always feel like home, and picking up the little piece of ourselves that we left behind. And that is when it happened. Two beautiful, young graduates came and sat with us. One of them asked, so what was this place like for Black people in the 1990s?

We all looked at each other and chuckled.

We reached for the sensational details first — the ones designed to impress. Like Lauryn Hill performing when she was still with the Fugees.

They looked back at us, confused.

Who are the Fugees?

Reflecting on that moment, this is what I wished I had shared with these two graduates:

We are the American Exceptions. We are not of the old world, but raised by Old Worlders.

We are the In-Betweeners, made in the Different World. We are some of the first to practice democracy in the classroom and laboratory, with many races, at the bus stop, and in the library and stacks. We had the chance to learn in the place where our ancestors built with their hands. We had the chance to practice democracy in the dorm rooms and suites, at football and basketball games. We are some of the first to know what it feels like—the pleasure and pain, the sweet and the sour, what it feels like to be closer—the risk and reward. We are among the first Americans to taste it, recognize it, and know that it's not only possible but also an imperfect practice worthy of our human effort.

Our democracy is the Final Exercise.

This is what it means to wear the Honor of Honors.

Imposter syndrome was common at UVa, but we did not have a language for the phenomenon. But our difference did not make us impostors; it made us American Exceptions. Instead of following and fitting in, instead of numbing and romanticizing, instead of swallowing mythology, we created the new knowledge, truths, and dispositions for the most exceptional American story, desperate to be retold.

We are not impostors.

We are the exceptional ones. We need to stay that way.

Stay Maladjusted. Be Exceptional.

Caroline

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The Gladys Pilot is Open: Exceptional Ones Wanted

We are losing the leaders when we need them the most. 60% of K–12 educators report burnout, and 4 in 10 principals may leave within three years. The problem isn’t people — it’s design.

Gladys changes that. For five months, Gladys sits in your pocket as an AI equity coach — guiding your leaders through daily practice, monthly peer feedback, and a measurable journey toward equity-informed decision-making. Not a chatbot. A critical friend grounded in culturally responsive practice.

What you get:

• Daily 15-min AI coaching sessions personalized to each leader

• Monthly 90-min facilitated feedback sessions

• Community of practice with equity leaders across organizations

• Baseline + month-six equity leadership assessment

• Learn the tech by using the tech.

The math: Founding partners lock in at $33/leader/month — permanently. That’s 53% off the 2027 public rate of $70/leader/month. For 15 leaders, that’s $5,400 in annual savings. Forever.

Pilot begins August 1, 2026

Deadline to join: June 30, 2026

Ready to talk? Email caroline@228accelerator.com

Learn more: 228accelerator.com/gladys-pilot

We Are Gladys. Your critical friend.

We are Gladys. Your critical friend.

Community Spotlight: Ona’ Anosike, Inkwell Montessori

Learn More about Inkwell Montessori

Black Reconstruction: A Fleeting Democracy and Violent Suppression

The idea that everybody eats should not be revolutionary, but it is. This month, we discuss the legislation passed during the Reconstruction era and how it set the stage for modern race relations.

When we discuss anti-Blackness, it is not an abstract principle or theory. Instead, anti-Blackness often leads to the rejection of everything associated with Black people, even if it serves the public good, especially when it serves the public good. And everyone is vulnerable to anti-Blackness.

Public schools in the South were initially rejected because they were legislated by Black politicians. We see the same pattern with the rejection of universal healthcare and the divestment in public infrastructure. It sounds like it can’t help me if it helps them. It looks like: closing schools to avoid integration. It looks like filling in the public schools with concrete. This rejection is driven not by merit but by primal fear and hatred. It is not democratic.

Join us to practice democracy together.

Join us to practice democracy together.

Lit — What We’re Reading and Writing This Season

We are working on a few essay-articles about teacher feedback, thinking, being, and leading differently. In the meantime, sweeten your tea with this sugar…

Right now, many of us are being asked to lead — perhaps in familiar ways and perhaps in new ones. We have seen deaths that we cannot unsee. We are collectively experiencing a loss of comfort and uncertainty as the ground beneath us trembles under the weight of universal suffering. Especially during crises, we crave strong leadership and direction. But when we are the ones being asked to lead in the moment, how do we do it?

Because underneath the laughter and the disbelief was a real question about power, boundaries, and who gets to decide what’s “normal” in shared spaces—especially when children are involved. And that question turned out to be the perfect threshold for the work we were about to do.

How food, Philly, two screens, and the Seedkeepers sharpened the work

The meeting didn’t start with strategy.

It started with a child pretending to be sick.

I checked in—because that’s what we do—and one of the Seedkeepers told the story of a four-and-a-half-year-old who had just learned the ancient art of “I do…

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This one started with weather, storms rolling up the coast, and a story about a lizard.

Not a metaphorical lizard. An actual classroom lizard.

It sounds small. It wasn’t.

Because underneath the laughter and the disbelief was a real question about power, boundaries, and who gets to decide what’s “normal” in shared spaces—esp…

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The grief that we are experiencing is crippling. It weighs on us mentally, but it can also change our physical postures — the way we stand in the world. As we work to regain a stable footing in the new world we are leading and creating together, attention to the body is critical. Just as the strongest person can injure themselves by lifting a heavy load incorrectly, we must now attend not just to our strength, but to our postures as well.

In designing, building, and leading amid uncertainty and crises, this balance is essential. In our leadership discourses, we often talk about strong leadership, but we rarely consider leadership postures. How are we holding our leadership? What does strong leadership look like in crises? What does it look like when we share our strength? When we are all asked to stand on what feels like shifting sand, what postures give us the capacity to hold and support others?

The art of equitable leadership through crisis is not just holding fast or even moving fast — it is understanding the ground, knowing who shares it, and adjusting our posture accordingly. With months, if not years, of a “new normal” ahead of us, we must embody the leadership postures that will allow us both to lead effectively and to maintain the strength required for leadership.

Posture 1: The Politician

Politicians get things done. They see and balance the needs of all constituents and remain principled in the face of challenges. They understand that they belong to the people and that the people hold them accountable. Equitable politicians prioritize the experience of the powerless and historically marginalized when making decisions.

The politician’s posture may be especially helpful when certainty is lacking. They stay proximate to the most marginalized and excluded while co-creating to-do lists and breaking seemingly overwhelming projects down into more manageable pieces.

Posture 2: The Pastor

The pastor is the shepherd — the one who creates space to nurture and care for people on the journey. The pastor moves with radical grace and mercy. They know that people may say the wrong things at the wrong time. When we fall, they remind us to practice radical grace and remember the divine in ourselves and keep trying. They know that the struggle is eternal, refuse to shy from challenge, and remind us of our innate power to become great.

The pastor’s posture brings compassion in times of crisis, especially as the stress of suffering reveals our unique vulnerabilities and shortcomings. Transformative and equitable leadership in this moment not only understands the need to accomplish, but it also embraces and holds us while we work. Leading in this posture is the big hug we all need, especially when we don’t show up as our best selves.

Posture 3: The Prophet

Prophets see what others cannot. They hold a vision of the future that might seem unrealistic, unfathomable, or even crazy. They are willing to “take one for the team” and are resilient in the face of challenges and adversity. They go first, set the vision, and inspire others to join them. They are joyous in the struggle and humbly hold their power to create a new world.

In the prophet’s posture, leaders ask their communities to extend their sight and believe in things they cannot yet see. They ask us to see the future we wish to realize, give hope in the possibility of that vision, and encourage members of a community to unite behind a common goal. In times of despair, they see the power for transformation that lives in each of us and leverage both integrity and vision to maintain engagement in the face of the most formidable challenges. Prophets humbly hold their power to create a new world.

Close your eyes and take three deep breaths. As you reflect on your leadership stance, which words and phrases resonate in your body? What is your default posture? How can you adjust, minute by minute, to the needs of our community?

This is the time to reflect on how we stand in the world, reassess our postures, and hold ourselves differently. Without this care and attention, we may not see how moments of crisis can open us to new possibilities and help us emerge as the leaders we were meant to be. There is always light in darkness, and new postures can help us see it.

I never felt like an imposter through the lens of academic achievement thanks to teachers and a supportive community that nurtured me as a child. And while that academic achievement was seen as body armor, it was also ritualized as a declaration of full humanity—every award, recognition, every graduation was another ethereal ancestral fever dream of a future that could not be seen, let alone imagined. A purification ritual in a world thriving on dehumanization, if you will.

I was not an imposter through the lens of achievement, but as I have matured, I know that I am an imposter through the lens of being. Let me tell you what I mean:

• I practice yoga and meditation daily, have for 10 years, and do not identify as a yogi or call myself one.

• I write daily and have done so for the past 10 years, and I will be published by the end of 2026, but I do not identify as a writer or call myself one.

• I am designing and building a technology, studied engineering, and geek out over both modern and ancient technologies while creating Gladys in a human-centered way, yet I do not call myself a technologist or identify as one.

For me, the imposter did not appear to be someone who feels they do not belong in someone else’s world. My imposter shows up when I do not feel like I belong in and fully acknowledge the world I am creating. And with all of that, by default participating in my own small dehumanization—again not shrinking into another’s definition of me, but not expanding into my full definition of self. Breathe.

And maybe this is what Audre Lorde meant when she said that, “If I didn’t define myself for myself, I would be crunched into other people’s fantasies of me and eaten alive. And to take it one step further, if I do not define myself for myself, I will never become myself. I never show up.”

So that stops now. I am different. I am the yogi, the writer, and the technologist. And that difference is strength.

Are you different? Or just like everybody else. How does your difference show up?

Stay Maladjusted. Stay Different.

Caroline

Share The Praxodox: Remaking Ourselves and Our Relationships

Q: Gladys has a brain? A: Well, sort of.

I don’t mean that figuratively. Right now, my engineer and I are loading the full equityXdesign curriculum into the AI — every step, every reflection activity, every archetype, every breath practice, and several historical figures who have led humanity over the past century. All of it is being translated into a knowledge structure that will influence how Gladys patterns, what it highlights, and how it guides leaders through the toughest parts of leadership.

Most people who follow a product build see the interface. The logo. The landing page. The demo app.

They don’t see this part.

This part is where we decide how an AI reasons about equity. How does it connect and parse language and make an assessment of progress? What language patterns signal human-centered learning — from hedging to owning, from abstraction to specificity, from describing the problem to naming their own role in it. How does it know which question to ask next based on where someone actually is in their journey, not where they report themselves to be? How does it know its own limits?

I have spent the last several months building a version of that map and knowledge graph. It is the most intellectually demanding work I have ever done. And it is also, I think, the most important, because it is the difference between an AI that gives leaders information about equity and an AI that may actually enable humans being. And when I reflect on the whole process, three insights sharpened:

1. Gladys is not a chatbot. It is a critical friend-ish. It reflects your context, connects where you have been, and prompts the question that expands a leader’s capacity and courage to see, be seen, and foresee.

2. It is built on equityXdesign. A framework that has been tested in real rooms with real leaders doing real work. And right now, it is connecting a corpus of many stories written and rewritten in one language. The map comes alive when we build it together.

3. Co-creation is a practice and not a performance. We are entering the pilot phase, so we’re actively seeking districts, school networks, and organizations that are deeply committed to sustained leadership development and want to be among the first to co-create how Gladys can nourish and uphold humans being.

If that is you — or if you know someone it might be — I would love to hear from you. Message me at caroline@228accelerator.com.

We can rock this earth’s foundation.

Check out the demo here.

Community Events: Black Reconstruction and AI Tool Creation

What happens when democracy is overthrown for being too democratic?

For over a century, the story of Reconstruction has been buried under what one historian called “a cloud of charges, exaggeration, and biased testimony.” But we went to the receipts. When the Black working class took power in South Carolina between 1868 and 1876, they built the state’s first free public school system for all children, abolished racial distinctions in the state constitution, passed the first divorce law, and protected married women’s property from their husbands’ debts. They built something that worked — and that is precisely why it had to be erased.

White supremacy does not survive black intelligent, competent freedmen and women leading the country. White supremacy does not survive the multiracial economic coalition—especially black-white. Something had to give, and it was not white supremacy.

The planter class’s strategy was simple: control hiring, control land, criminalize resistance, and flood the record with corruption narratives until the truth drowned in the blood of the working class. The planter class’s goal was clear: Return the United States of America to a slave economy. It is tradition. Democracy need not apply. Clear and simple.

Democracy with white supremacy is not democracy. It enables slavery. The planter class exploits the working class by using race as a wedge.

Workers war, planters hoard.

One hundred and fifty years later, that same playbook is running — mass firings hollowing out the Black middle class, homeownership priced out of reach for too many, and the violent intimidation, abduction, and kidnapping of the most vulnerable in the working classes. This is 1876 in 2026 clothing.

When we don’t know the history, we mistake the pattern for something new. It is not new. America without slavery is new. America without slavery is the exception. And we are living in it, which means those who want the old order back are working overtime.

Here’s what this moment demands: not just knowing the history, but having the tools to see it in real time, name it clearly, and build something better anyway. That’s what Freedom School is for. And right now, AI is the new terrain where the same battle over knowledge, access, and whose story gets told is being fought — which means it’s also where your power lives, if you know how to use it.

Come catch this lesson.

RSVP for Community Events

Lit — What We’re Reading and Writing This Season

We are working on a few essay-articles about teacher feedback, thinking, being, and leading differently. In the meantime, sweeten your tea with this sugar…

Culture and the Senses: Bodily Ways of Knowing in an African Community

“Words do not just have meaning-they are breath and vibrations of air, constituted and shaped by the body and motives of the speaker, physically contacting and influencing the addressee. So informants liken the effect of a griot’s praise-song on his addressee to the effect of wind upon fire (both metaphorically and literally, since air and fire are supposed to be basic constituents of the body). (Irvine as quoted by Stoller 1984b:567)

“Virginia State came up. Trojans. Hampton. Reconstruction-era artifacts. The old “normal school” lineage. The sacredness of institutions that were built to teach people the world insisted shouldn’t be taught. That mattered.”

“The UX designer’s experience with Kawaii—an open-source AI project for academia—made this concrete. He walked through a workflow where teachers create their own AI assistants: selecting the education level, choosing a persona, layering in frameworks, adding knowledge, then publishing and testing.”

It wasn’t just Michael B. Jordan’s brilliant technical performance that arrested my soul; it was hearing Black men on screen who sounded like my granddaddies—and their granddaddies. My dad exhaled audibly during one scene, as if he himself had ridden through those same fields as a young boy.

I shared 'One Battle After Another' with my sister. We gasped at every scene, saying again and again, "We can’t believe we are seeing this, especially right now." It was not just the different images of Black women— from Perfidia Beverly Hills and the Revolutionaries to the Grandmothers and Aunties to the Sisters of the Brave Beaver—that were stirring; it was that they were all part of the same story, together. The plot was familiar, but the roles this time, however, were very different.

This was the moment I didn't realize I needed to see. I didn't know moments like these could spontaneously awaken the parts inside me that had lost sensation—the deep interior parts that had forgotten how to focus and see, the ancient parts that drummed were muted into silence. I had not realized that I had forgotten to dream bigger.

Stories heal and can put us back together again.

Dream bigger was my intention for the week, and to use my body to write a new story, not for an organization’s or school’s mission. That is fine, admirable, and righteous. But to write a new story with my body for my body? That is the revolutionary virtue for everybody.

Each of us has a new story inside of us that needs to be told right now. Let’s dream bigger and tell it.

In this issue, catch up on the story of Gladys, The Equity Co-Pilot, and Freedom School 2.0: Black Reconstruction.

Stay maladjusted and connected.

Caroline

Gladys, The Equity Co-Pilot Update

Tomorrow, our monthly co-creation session with our community opens. And we know how full this moment is. That’s exactly why we’re building Gladys—not to add more, but to make reflection, collaboration, and leadership practice more doable in the middle of real work.

We’re entering the next phase of the Gladys Equity Co-Pilot, and one thing is becoming clearer by the day: this isn’t just about a tool. It’s about building the kind of shared practice that actually shifts how we lead, decide, and show up for young people and ourselves. At its best, Gladys acts as both mirror and guide—helping leaders move from intention to daily action, with support that is responsive, personal, and grounded in real relationships. Because the goal isn’t faster answers. It’s better practice.

And we’re holding a clear line: the learning has to be compelling enough that people return to it—and relational enough that it connects people to each other, not replaces them. It must be irresistible. Equity work must be irresistible.

If you’re a principal, teacher leader, district leader—or someone building leadership in any form—this space is for you. And if you’re feeling called to go deeper, we’re also inviting a small group to become founding members of Team Gladys.

Founding members won’t just use the tool—you’ll help shape it. You’ll influence how this human-centered technology grows, what it prioritizes, and how it stays grounded in real practice and real people. This is about building something with you, not for you.

Join us tomorrow. Consider stepping in as a founding member. Help shape what this becomes. Because if this is going to work, it has to be built with the people who will carry it forward.

Freedom School 2.0: The Black Proletariat in South Carolina

There’s a story we’ve been told about Reconstruction—that it failed. But what if that story was written to make us forget what actually worked?

In South Carolina, from 1868 to 1876, a newly enfranchised Black working class didn’t just participate in democracy—they reshaped it. They built public education systems, expanded rights, and governed with the well-being of the whole in mind. And then, that story was buried—replaced with one that made their success invisible. Take a moment to watch the video.

Because the challenge in front of us isn’t just about policy or practice. It’s about story.

If we inherit incomplete stories, we build incomplete futures. So the question becomes: what story are we willing to tell now—and what will we build from it?

Freedom School 2.0 is a space to study these hidden blueprints and begin designing forward together—not as theory, but as practice.

Join us live at 10 am and 4 PM for our Freedom School conversation.
The chat is open all day. Drop in, reflect, and build with us in real time.

We need better tools, a new story, and the courage to live it.

Lit — What We’re Reading and Writing This Season

Equity work is an antidote. It’s still the antidote. That’s why it’s under attack. And if AI is going to flood the system with noise, then we need to automate the antidote—carefully, precisely, and quickly—so we don’t destroy communities while pretending we’re “innovating.”

“I said it plainly: there are adults who want a trusted guide, because they’ve inherited shallow or inaccurate stories about history and struggle. They want to build better relationships across differences. They want “nudges” toward decency. They want to show up better in the community.”

“But momentum didn’t come from capital alone. Around the same time, I had just completed an MIT XR/AR course—deepening my understanding of immersive design—and participated in Black AI Literacy Week. These experiences didn’t add bells and whistles to the project. They sharpened the stakes. If board members, school leaders, and educators were going to step into this future, confidence—not novelty—had to lead.”

This one started with names—because we were already laughing at how many times we’d introduced ourselves—and with the kind of origin-story signals that tell you who you’re really talking to.

Virginia State came up. Trojans. Hampton. Reconstruction-era artifacts. The old “normal school” lineage. The sacredness of institutio…

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They feel like two people trying to tell the truth out loud—about what’s hard, what’s possible, and what the user will never forgive you for ignoring.

This one started with life stuff: I’m selling a house, juggling a thousand moving parts, and navigating the politics in the air. The kind of week that quietly sets the stakes. Because when your life is full, you don’t have patience for clunky tools. And educators—especially school leaders—live in “full” as a permanent condition.

Then the UX designer shared something deceptively small: the experience of using Google’s AI assistant.

Not the model. Not the intelligence.

The feeling of it.

A clean interface. Subtle movement. A spectrum of color that made the tool feel alive without turning it into a cartoon. Personality without a face. Help without intrusion. It didn’t demand attention—it earned it.

And right there, the design challenge for Gladys snapped into focus:

How do you make an AI assistant feel inviting, without making it feel like a toy?
How do you make it clear, without making it cold?
How do you give it soul, without overwhelming the user?

That’s the line we walked for the rest of the conversation.

“We’re Not Just Building a Tool. We’re Building Adoption.”

This is where the Gladys project keeps distinguishing itself from the pack.

Because the market is full of “AI for educators” tools that assume the only job is shipping features. But what I keep naming—again and again—is the second job:

teaching leaders how to use the tool in a way that changes practice.

Not tutorials. Not onboarding fluff.

Actual workflow design. Actual trust-building. Actual “I can use this in the middle of a hard week” usability.

The UX designer’s experience with Kawaii—an open-source AI project for academia—made this concrete. He walked through a workflow where teachers create their own AI assistants: selecting the education level, choosing a persona, layering in frameworks, adding knowledge, then publishing and testing.

The big takeaway wasn’t “we should copy this.”

It was: the logic matters.
If the journey isn’t coherent, the user drops off—even if the tool is brilliant.

So instead of polishing screens, we did the real work: defining who Gladys is for and what she’s actually supposed to do.

The Breakthrough: Let the User Choose the Model

Then we hit the idea that quietly rewired the platform:

What if Gladys allows users to choose their AI model inside the experience?

Not as a gimmick—but as a relief.

Because the reality for many power users is messy: one account for ChatGPT, another for Gemini, another for Claude, another for whatever comes next. Switching contexts. Re-learning interfaces. Fragmented workflows.

So I floated the hypothesis:

If a user can choose their model inside Gladys, Gladys becomes the umbrella—one home, many engines.

The UX designer confirmed: yes. That’s one of the strongest value-adds in platforms doing this well.

But the real magic wasn’t consolidation.

The real magic was education.

I pushed it further:
If users choose the model, Gladys can teach them how to choose.

Pros and cons. Best-fit recommendations based on intent. Signals like: “This will get you 80% there, but it still needs your human touch.” The goal wasn’t to turn educators into engineers.

It was to build discernment.

Gladys wouldn’t just be a tool. It would be a training ground for becoming a critical consumer of AI.

That’s not a feature. That’s philosophy.

Personas: The Project Moves from “Who Might Use This?” to “Who Is This For?”

At a certain point, the UX designer did what great product leaders do: he made the conversation choose.

“Let’s define personas. Who is Gladys for?”

I answered in three layers—then immediately wrestled with the consequences of my own ambition.

1. School leaders (principals, assistant principals, aspiring principals)
   People who influence adults. Their sphere of influence is many classrooms. Their job is culture, coherence, professional learning, and the conditions for achievement.

2. Educators/teacher leaders (department chairs, coaches, PTA leaders, specialist teachers)
   People who influence students directly. Their sphere is the classroom, but the ripple is deep.

3. Adults outside the schoolhouse who want to grow
   This part got messy fast—not because it’s wrong, but because it’s huge.

I said it plainly: there are adults who want a trusted guide, because they’ve inherited shallow or inaccurate stories about history and struggle. They want to build better relationships across differences. They want “nudges” toward decency. They want to show up better in the community.

That’s a real audience.

It’s also a trap if you try to build it all at once.

So we named what mature builders always name:

Start where you have credibility. Build the foundation. Earn the right to expand.

That meant staying disciplined in schools first—leaders and educators—because that market is already massive and the user context is known.

The Unifying Product Promise: “Gladys Redesigns Relationships to Build Trust”

In the middle of all the personas, I returned to the brand spine—the sentence that has guided my work for years:

Design relationships to build more trust.

And suddenly the whole conversation had a headline.

Gladys does that work in different spaces:

• If you’re a school leader, it helps you do it in the schoolhouse, so you can sustain a culture of high academic achievement.

• If you’re an educator, it helps you do it in the classroom, so students experience belonging, challenge, and coherence.

• If you’re an adult in the broader community, it helps you do it in your relationships and civic life, so you can show up with more integrity.

Same spirit. Different context.

That’s a product strategy.

The Real Deliverable Isn’t Screens. It’s a Narrative.

Near the end, the UX designer said something that explains why this project is moving:

He’s not designing “a set of screens.”
He’s designing a story.

The personas inform the use cases. The use cases inform the interaction points. The interaction points become the prototype. And the prototype becomes the narrative that a user can walk through and say:

“Yeah. This is for me.”

The action plan was clean:

• The UX designer synthesizes the personas and epics into a crisp write-up

• I validate the language, especially the brand coherence

• Then the UI gets built with intention, not guesswork

• The tech team shares additional research and insights on what future learning tech needs to support educators well

Why This Moment Matters

This wasn’t a brainstorming session about features.

This was a team deciding what kind of product we’re building:

Not a flashy AI wrapper.
Not an “everything app.”
Not a tool that pretends to be neutral.

Gladys is shaping up to be something rarer:

A human-influenced AI assistant that helps educators build trust, strengthen culture, and make better decisions—while also teaching them how to be discerning about the technology itself.

That’s not just useful.

That’s durable.

And in this moment we’re living through—where noise is cheap and trust is scarce—durability is the whole game.

I celebrated my in-laws’ 50th wedding anniversary — an interracial marriage that only became legal because Mildred and Richard Loving refused to accept a world that criminalized their love. I stopped in Cleveland to sit with the history of Relay and the desegregation efforts that left generations of Black children carrying what scholars call instructional debt. And I walked the Legacy Sites in Montgomery, Alabama, standing inside the weight of what was taken and what was survived.

Each of these experiences arrived as its own gift. But together, they cracked something open.

A central story finally unlocked — one I believe connects everything we’re building. Our curriculum. Our assessments. Our badges. Our vision for what learning can do.

After Cleveland. After watching my father at VSU. After finding the names of my ancestors—maternal and paternal—on the Monument to Freedom, one question has risen to the surface and refuses to leave: Who would we be if colonization, slavery, and segregation had never occurred? Who can we be now?

That question is now the spine of everything — our stories, our curriculum, how we walk alongside educators doing this work.

Not as an academic exercise. As a design question. As a north star.

This is the story to write now. Otherwise, we are featured in someone else’s sick fantasy.

Honor the Authors

In every edition of this new newsletter, we will honor the Authors in our community— those who build with intention, create with courage, and send light into the darkness the way our ancestors always did: quietly, persistently, and without asking for the world's approval.

When systems close the pool, Trish builds a swim school. When classrooms silence students, Eric builds a movement. This is the through line of our community — we don’t wait for the world to make room. We design the room ourselves.

Their work matters now because the pressure to abandon equity is real. The defunding is real. The book bans are real. And so is the resistance.

The Authors in this community are proof that another world is not only possible — it’s already being built.

Building something that deserves to be seen? Tell us your story. We’ll help you tell it louder.

Lit — What We’re Reading and Writing This Season

Think of this as your reading shelf. Each season, we curate the articles from our archive worth saving — the pieces that named something important, opened a new door, or gave language to what you were already feeling. Add them to your library. Return to them often.

How to AI: Labor, Power, and Literacy in a Machine Age -Part 1: “For enslaved people, learning to read was not an abstract aspiration. It was a radical act. They described literacy as “talking to books” and “catching a lesson.” These phrases reveal something profound. Literacy was not consumption; it was conversation. It was the act of seizing knowledge that had been intentionally withheld. It was treated as contraband precisely because it expanded imagination and coordination.

Quest 23: Compare the Models and Tools: “Goal: To develop AI fluency by understanding how large language models work, distinguishing between different types of models (general vs. reasoning), and recognizing the difference between generative and agentic AI — so you can apply the right tool to the right real-world problem with discernment.:

Kwame Ture Addresses the Black Panthers: If institutions are designed to control you, then you don’t “fix” them with hope—you build the capacity to protect each other, organize together, and act with discipline. For educators, this matters because the speech refuses “neutral.” It argues that schools and social programs are not simply services—they’re tools that can be used to manage, split, and pacify communities unless communities actively shape them.

The world is mutable. That is the thread running through every story in this edition. Charlie Hill gave. The Lovings loved. Trish built. Eric listened. And somewhere right now, someone in this community is writing the next chapter. We cannot wait to tell your story.

See you in the comments and in the chat.

Leave a comment

Goal: To develop AI fluency by understanding how large language models work, distinguishing between different types of models (general vs. reasoning), and recognizing the difference between generative and agentic AI — so you can apply the right tool to the right real-world problem with discernment.

This is not about hype.
This is about judgment.

And remember: the field is evolving quickly. By the time you are reading this, there may be new models or capabilities. Your aim is not to memorize product names — it’s to understand principles that transfer across tools.

Role: You are a Model Explorer. Not a passive user. Not a cheerleader. Not a skeptic standing outside. You are an investigator of thinking systems. Your job is to observe how models structure responses, notice differences between speed and depth, identify strengths and weaknesses, reflect on what kind of cognition each system amplifies.

You are building discernment and the confidence to share with others.

Audience: Your team and community.

That is literacy in this era.

Situation: We are living through another Reconstruction. After the Civil War, the United States had to renegotiate labor, capital, and citizenship. Du Bois argued that slavery was not marginal to capitalism but foundational, and Reconstruction sought to rebuild the nation’s moral and economic architecture. Today, artificial intelligence is again reshaping labor, ownership, and value. Economic systems do not vanish; they evolve. If earlier generations had to read contracts and ballots, we must now read algorithms. Large Language Models predict patterns from historical data, inheriting its assumptions. Without discernment, they risk scaling inequality rather than transforming it.

Within this ecosystem, you will encounter:

Performance: Approach this work with disciplined observation and reflection. Choose one general-purpose model and one reasoning model, and give both the same complex prompt. Compare their speed, structure, confidence, assumptions, and moral framing. Then push further. Ask each model what it is optimizing for, request a critique of its own response, identify missing data or perspectives, and consider who might be harmed by uncritical reliance. Finally, zoom out. Examine the worldview embedded in each output, whose labor remains invisible, who owns the infrastructure, and what happens if these systems scale. Discernment means evaluating not just answers, but the systems producing them. (see the worksheet below)

Product: Produce a short AI Fluency Brief (1–2 pages or 5–7 slides) that clearly explains, in beginner-friendly language, how Large Language Models work, including how they predict patterns and why probability differs from human reasoning. Include a comparison chart distinguishing General vs. Reasoning models and Generative vs. Agentic AI. Document your observations from experimentation, noting differences in speed, structure, assumptions, confidence, and moral framing. Offer three practical recommendations: when to use each type, risks to monitor, and essential questions leaders should ask. Conclude with a reflection on what surprised you and share your learning with two others to build collective literacy.

Complete the sentence: As I reconsider AI, I used to think______________, but now I know_________ .

Resources:

228 Ai Models Cheat Sheet V3 Branded

33.5KB ∙ PDF file

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Download

Ai Discernment Worksheet 228 Accelerator

32.2KB ∙ PDF file

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