What Does It Take to Fund Imagination?

Proposal: What Does It Take to Fund Imagination?

Applicant: A practitioner walking an unfinished road

Caminante, no hay camino — se hace camino al andar.
Traveler, there is no road. The road is made by walking.

1. Problem Statement 

Across the social impact landscape, there exist hundreds—likely thousands—of thoughtful, careful, deeply committed proposals that never receive serious consideration. Not because they lack merit, but because they aim to do work that is difficult to quantify with our current tools. They seek to shift mindsets, relationships, narratives, and cultures—the very conditions from which lasting transformation arises.

We operate within a funding ecosystem designed for projects rather than people, for predictable outputs rather than emergent learning, and for short-term proof rather than long-term transformation. In this ecosystem, imagination is praised rhetorically but rarely resourced materially.

We fund activities, but not the inner work that makes them meaningful.
We fund outputs, but not the worldview shifts that sustain change.
We fund what is visible, but overlook what is necessary.

As a result, practitioners are often asked to compress complex, relational, imaginative work into forms that favor certainty over curiosity and speed over depth. The work is reshaped to fit the metrics, rather than the metrics evolving to meet the work. Much is lost in this translation—especially proposals that seek to cultivate possibility rather than guarantee outcomes.

At the center of this problem lies a quiet truth that is widely shared but rarely spoken:

If practitioners had a living wage and long-term stability, much of this work could actually unfold.

2. Proposed Solution

This proposal is not for a single program or initiative. It is an invitation to rethink what we fund—and how.

If imagination is essential for navigating social, ecological, and cultural complexity, then imagination itself must be resourced. This requires funding approaches that behave less like transactions and more like companionship.

What this means in practice is support that offers:

  • Multi-year commitments that provide stability rather than perpetual precarity
  • Trust-based relationships grounded in shared learning
  • Space for emergence instead of predetermined certainty
  • Funding for practitioners, not only for deliverables
  • Accountability rooted in reflection and adaptation rather than prediction

When funding honors the slow, relational, meaning-making dimensions of change, practitioners are able to remain in the work long enough for transformation to take root. The result is not less rigor, but deeper integrity.

3. Project Activities

If imagination were taken seriously as a driver of transformation, the core “activities” might look different from what most proposals describe.

They might include time to think—still a radical act in a culture of constant productivity. Time to develop shared language for work that does not yet have a common vocabulary and/or lexicon. Slow cultivation of relationships with communities, not as pipelines or beneficiaries, but as collaborators in meaning-making.

They would include iterative prototyping that is allowed to be nonlinear and unfinished, sensemaking with peers navigating similar uncertainty, and reflection and storytelling treated as central practices rather than optional add-ons.

This is the work behind the work. It is often invisible, rarely funded, and yet indispensable for any change that hopes to last.

4. Budget Overview

A humane budget for imagination-centered practice acknowledges that imagination is labor.

Such a budget includes a living wage that allows a practitioner to remain in the work without chronic financial anxiety. It includes healthcare, stability, and protected time. It recognizes the contributions of collaborators and community partners through stipends rather than extraction.

It supports travel to the places where learning actually happens—not only to where the work is presented. It allocates resources for reflection, design iteration, and documentation. It protects time for reading, wandering, listening, and synthesis—the incubation periods from which insight emerges.

This logic has guided my work for years, including the development of The CAMINANTE Project: the recognition that sustainability for the practitioner is not indulgence. It is infrastructure.

5. Monitoring and Evaluation

Traditional monitoring and evaluation frameworks struggle to capture emergent, relational work. Yet imagination leaves traces, even if it cannot be reduced to a single metric.

Meaningful indicators include the quality and durability of relationships formed, shifts in language or framing within a community, changes in how people understand their agency, and early signs of cultural momentum. Practitioner sustainability—financial, emotional, relational—is itself a critical indicator.

Other signals may appear indirectly: unexpected invitations, new collaborations, stories that begin to circulate, experiments that open doors even when they “fail.”

Imagination cannot be neatly quantified, but it can be followed—like footprints across soft ground.

6. Expected Outcomes

If imagination were resourced with patience and trust, we would expect to see work with deeper ethical roots and longer lifespans. Practitioners would no longer need to contort their vision to fit short funding cycles. Funding ecosystems would begin to align more closely with human and ecological rhythms.

We would see cultural narratives shift slowly but perceptibly. We would see more proposals that do not promise certainty, but offer honesty. And we would see a growing number of CAMINANTES—walkers, seekers, wayfinders—creating paths that do not yet exist.

This is not idealism. It is simply what becomes possible when funding aligns with how transformation actually unfolds.

7. Vision Statement

A future in which those doing slow, relational, imaginative work are not surviving on the margins, but are supported with the time, trust, and stability their contributions require. A future in which imagination is recognized as essential civic infrastructure. A future built not through speed or spectacle, but through steadiness—through roads made by walking.

Leading by Listening: Rhythm, Energy, and Positive Leadership

There are days when leadership feels like a rush of motion — emails, calendars, demands, decisions. The pace accelerates, and we move with it. But beneath the surface of all this activity, there is always a quieter layer: a rhythm.

My recent Positive Leadership course at the University for Peace (UPEACE) helped me remember how to recognize it.

Leadership begins not with a plan, or a metric, or even a vision — but with presence.

The course invited me to listen again underneath the noise of tasks and timelines — to notice the rhythms that shape how we lead and live. We often imagine leadership as direction: setting goals, driving momentum, managing outcomes. But positive leadership asks a subtler question:

What energy do we bring into the systems we inhabit?

That shift — from managing performance to managing presence — reframed leadership for me. It is less about control than about rhythm:  the ebb and flow of awareness, connection, and meaning through time.

Listening for Rhythm

Henri Lefebvre, in his Rhythmanalysis, wrote that every space carries its own pulse — its repetitions and variations, its silences and surges. The city breathes through its traffic and stillness; the body through its circadian tides.

Positive leadership, seen through this lens, becomes a kind of rhythmanalysis — a discipline of attention. It calls us to attune to the living tempos of our work and relationships, to sense when we are in harmony and when we have fallen out of tune.

The course began with this act of listening. We mapped our values, charted our daily energy, and reflected on what gives us vitality and what drains it. Through Simon Sinek’s Start with Why, we traced the pulse of purpose within our professional lives.

Meaning is not an abstraction — it is what sustains motion over time.

When I began mapping my own day, I saw patterns I had ignored: the quiet hours when creativity peaks, the lulls that invite rest, the shifts between solitude and connection.

As one fellow student put it:

“Positive leaders look for lasting impact from sustainable energy, not constant effort.”

Leadership, then, is not about enforcing a steady tempo; it is about composing harmony among these rhythms — the personal and the collective, the urgent and the reflective, the doing and the being.

Leadership as Energy Ecology

Much of what we call leadership is really about studying energy distribution — how attention, trust, and motivation circulate through a system.

Psychological safety, for instance, is not only an emotional condition; it is an energetic one. When people feel safe, energy expands — ideas flow, collaboration deepens, risk-taking becomes generative. When fear or cynicism take hold, energy constricts.

This is where positive leadership differs from the merely productive. It is not about maximizing output but optimizing flow — creating the conditions in which energy replenishes rather than depletes.

The course grounded this in Martin Seligman’s PERMA model of well-being:

  • Positive emotion sustains hope.
  • Engagement anchors us in flow.
  • Relationships generate resonance.
  • Meaning aligns us with purpose.
  • Accomplishment gives cadence and closure.

Together, they form the architecture of flourishing — a living, breathing rhythm that holds both effort and renewal.

To lead positively is to become a rhythmanalyst of well-being: sensing where energy moves freely, where it stagnates, and how small, intentional shifts — a pause, a genuine question, a gesture of care — can restore equilibrium.

When Rhythm Is Broken

Of course, most of us do not work in environments where this rhythm comes easily.  Many of us have known workplaces where urgency overrides reflection, where performance outweighs presence, where people speak carefully rather than honestly.

This is not a failure of individuals — it is a failure of culture.

Psychological safety, we learned, is not simply “nice to have.” It is the precondition for creativity, collaboration, and adaptability. Yet it might be rare. To question, to dissent, to ask for alignment — these acts often feel risky.

Most of us have been in rooms where silence seems safer than contribution.  Where we sense a misalignment between the stated mission and the lived reality — and do not feel permitted to name it.

This course did not pretend otherwise.  It acknowledged that positive leadership often begins in tension — between how things are and how they could be.

To lead positively is not to ignore these fractures; it is to notice them — and then act in ways that widen the space for honesty, curiosity, and care.

Sometimes that means asking a different question.
Sometimes it means slowing the tempo when everyone else is speeding up.
Sometimes it means being the first person in the room willing to say, “We’re out of rhythm. Can we listen again?”

Positive leadership does not assume the rhythm is already healthy.
It creates the possibility for harmony to emerge.

The Sound of Integrity

One question echoed throughout the course:

Why should anyone be led by you?

It’s deceptively simple — and profoundly clarifying.  My own answer emerged through five values: communication, equity, service, kindness, and growth.  They form the chord through which I live and lead.

Leadership, I came to see, is not about volume but tone — not how loudly one speaks, but how well one listens.  Integrity, in this sense, is resonance: the alignment between belief, action, and presence.

When tone matches intention, people feel it.  The room steadies.  Energy gathers.  Positive rhythm returns.

Rhythm as Reflection

In Lefebvre’s terms, the rhythmanalyst is both participant and observer — immersed in the pulse of life yet aware of its pattern. The same is true of leadership.

The leader listens: to the tempo of meetings, to the pauses between ideas, to the subtle signals of fatigue or enthusiasm.

They adjust — slowing down where reflection is needed, accelerating when momentum builds, recognizing that renewal often begins in rest, not speed.

Leadership, reframed this way, is not control but choreography.

Toward a Rhythmic Practice

The course concluded with a Personal Leadership Plan — a living score for the symphony of one’s work.

For me, that plan centers on advancing The Geographical Imaginations Expedition & Institute toward nonprofit status — a project that, like a rhythm, has unfolded over time, layering inquiry, storytelling, and community engagement.

Yet beyond that plan, what remains is a practice:
to manage energy, not time;
to listen before leading;
to treat each day as both composition and improvisation.

Leadership, I’ve come to believe, is less a position than a rhythm — one that must be tuned and re-tuned, like an instrument in ongoing rehearsal.

Coda: Leadership as Listening

Lefebvre urged rhythmanalysts to “listen — listen to your body, to the city, to the world.”

Positive Leadership is that same act of listening applied to human systems.

It is rhythmanalysis in motion: sensing where harmony falters, where renewal is needed, where silence itself becomes a form of care.

If Regenerative Leadership taught me to see systems as living ecologies, Positive Leadership taught me to feel their pulse.

To lead, then, is not to command, but to listen into coherence — to transform effort into ease, intention into flow, and attention into presence.

Leadership, at its best, is rhythm made visible: a steady hand, a compassionate ear, and the courage to pause.  The work is not easy — but it is necessary. Because every culture we inherit was once constructed, and every rhythm can be rewritten.

The Work Between Elections

In 1949, my grandfather, J. Lawrence O’Toole, ran for mayor of Bridgeport, Connecticut. He was a bricklayer from Black Rock and a labor organizer who came into politics the slow way: through union meetings, community debates, and the kind of civic life that doesn’t announce itself as such. He challenged Jasper McLevy, the socialist who had governed the city for years and built a reputation for frugality and municipal steadiness.

My grandfather lost that election. For a long time, that loss was something my family referred to now and then, as if its meaning were already fixed. Yet as I watched Zohran Mamdani win the New York City mayoral race this week, that story opened back up. Mamdani, a democratic socialist shaped by tenant organizing and neighborhood mutual aid networks, did not win because of a sudden surge of ideology. He won because civic participation had already been happening — patiently, consistently, out of public view — long before Election Day.

This is the part of politics we rarely describe honestly. Campaigns are not really about speeches, slogans, or personality. They are about whether neighbors talk to one another; whether communities build institutions that last; whether people believe that participating in public life is worth their time. Elections are not causes. They are outcomes of civic work already done.

My grandfather belonged to a version of civic participation grounded in labor. Workplaces were where political life began. The union hall was a form of local government long before City Hall entered the conversation. Bargaining was not abstract; it was a daily negotiation over safety, wages, and dignity. To run for office as a labor leader was simply to extend the logic: if working people live with the consequences of municipal decisions, they should help make them.

McLevy’s supporters saw civic responsibility differently. Their version of public life emphasized stewardship — careful budgets, transparent management, and insulation from corruption. They believed that participation meant oversight and accountability. These were not opposing social classes. They were two different theories of how people should work together to govern themselves.

What connects 1949 Bridgeport to 2025 New York City is not the ideology of socialism. It is the recognition that civic participation is a process, not a performance. Mamdani’s win was not spontaneous. It was the product of tenant organizers knocking on doors year after year, of neighborhood groups coordinating across blocks, of residents building trust in one another long before they were asked to build trust in a candidate. The election did not create that civic infrastructure. It revealed it.

And this matters because of what comes next. Winning elections has a way of disguising how fragile civic participation can be. When a movement gains power, the work changes. Governing requires translation, compromise, patience, and the willingness to hold together coalitions that are not as unified as they once appeared. The meetings get longer. The disagreements get sharper. The stakes get more real. The romance fades and the work begins again.

This is where my grandfather’s story remains useful. His loss did not erase the civic networks he helped build. The labor movement in Bridgeport did not end with that election. It shifted, reconfigured, and continued to shape how working people engaged in public life. Losing did not mean disappearing. Losing meant the work moved into another form.

And winning will require the same perseverance. The civic networks that carried Mamdani to office will need to stay intact, not for celebration but for governance. If they become symbolic instead of practical, the victory will be temporary. If they remain functional — if participation continues when the cameras are gone — then something more durable will have been achieved.

The easy story would be to say that democracy spoke clearly last night. But democracy does not speak clearly. It speaks in fragments, in efforts, in partial agreements, in structures people build piece by piece. It speaks through the slow work of organizing, showing up, listening, arguing, and returning to the same room the next week.

If there is a lesson that connects my grandfather’s loss to Mamdani’s win, it is this: Democracy is not what happens on Election Day. Democracy is the work that makes Election Day matter.

The vote is not the end of participation. It is the evidence that participation happened.

And it has to keep happening.

The work is not the victory. The work is the participation.  And the work continues.

 

Regeneration as Leadership, Leadership as Regeneration

Some courses give you tools. Others give you perspective. This one offered both — but, more importantly, it offered a pause.

In studying Regenerative Leadership with the University for Peace (UPEACE), I came to see that regeneration is not, at its core, about projects, outputs, or even systems. It begins somewhere deeper: with consciousness. With how we see, how we listen, how we relate.

We tend to equate leadership with direction: setting strategies, assigning roles, measuring results. These matter, but they are not the heart of regeneration. What regenerative leadership asks is different:

  • Can you slow down enough to see the whole system?
  • Can you suspend assumptions long enough to imagine alternatives?
  • Can you listen deeply enough to hear what is not yet being said?
  • Can you act with courage, not just certainty?

This shift in emphasis — from controlling to cultivating, from planning to perceiving — is what makes regeneration different from sustainability. It calls us to work not only on external structures but also on the inner operating system of people and communities.

Regeneration as Spatial Practice

What struck me most is how this work is not only temporal but spatial. Regeneration requires creating the spaces — physical, social, and symbolic — where new ways of seeing and acting can emerge.

Henri Lefebvre reminded us that space is not neutral; it is produced. Regenerative leadership echoes this insight. It is less about imposing blueprints and more about co-producing spaces of possibility. Spaces where trust can form, where silence can hold meaning, where imagination can stretch.

A workshop circle, a classroom, a village square, a Zoom call — these are not just “settings” for regeneration. They are living spaces, continually produced and reproduced through dialogue, practice, and power. To lead regeneratively is to attend to how these spaces are held, how they invite, how they constrain, and how they can be reimagined.

Regeneration as Liberatory Pedagogy

Here, critical pedagogy offers a vital reminder: education is never neutral. As Paulo Freire argued, it either domesticates or liberates. Dialogue, in this view, is not a technique but a stance — an encounter that affirms human dignity and makes space for learners to name their own reality.

Regenerative leadership, understood through this lens, is a liberatory practice. It resists the “banking model” of leadership — where solutions are deposited by experts — and instead insists on co-creation. It seeks not only sustainability but emancipation: to free people and communities from the limiting stories and structures that keep them from imagining alternatives.

Liberatory pedagogy also reminds us that spaces are contested. Who speaks, whose knowledge counts, whose silence is overlooked — these are questions of power. Regeneration cannot ignore them. To practice regenerative leadership is to surface these dynamics, disrupt domination, and create conditions where power is shared and agency is restored.

Weaving Quadrants, Co-Producing Space

One of the frameworks we studied suggested that regeneration unfolds across four quadrants:

  • the personal interior (mindset, values, purpose),
  • the personal exterior (behaviors, skills),
  • the collective interior (culture, shared vision), and
  • the collective exterior (systems, strategies).

Leadership, then, is the weaving together of these quadrants — tending to both the inner and outer, the personal and collective.

This weaving is a liberatory act of space-making. Every dialogue is a space produced. Every story is a re-mapping of possibility. Every collective reflection is a chance to reimagine power.

To lead regeneratively is to practice leadership as both spatial and pedagogical: shaping the conditions where people can not only adapt but also liberate themselves — from limiting mindsets, from unjust systems, from imposed futures.

Mindset as the Deepest Space

Donella Meadows reminded us that the deepest leverage point for system change is not policy or money — it is mindset. The stories we inhabit shape the spaces we live in. Change the story, and the space shifts.

This is where regeneration becomes both ecological and liberatory. It is about restoring ecosystems and economies, yes — but also about restoring the freedom to imagine, to name, to act. It is about cultivating relational spaces where people can encounter one another differently — and from that encounter, act differently.

Regenerate

I leave this course with new tools, yes — but also with a renewed sense of responsibility: to practice leadership as a regenerative and liberatory act of space-making.

To restore, reconnect, reimagine — and to liberate.
Not just for organizations.
Not just for projects.
But for the very spaces in which we live, learn, and become together.

Walking the Labyrinth

A Framework for Designing Inquiry-Based Expeditions

When we imagine planning an expedition, a project, or even a career step, it’s tempting to picture the path as a straight line: define the goal, create a plan, execute. But anyone who has actually walked such a journey knows it’s rarely so direct.

That’s why I turn to the metaphor of the labyrinth. Unlike a maze, a labyrinth isn’t about dead ends or wrong turns. There is only one path, and though it winds outward and inward, you always move toward the center. The gift of the labyrinth is that it reminds us: progress doesn’t mean walking straight ahead. Progress can mean circling back, pausing, or picking up new tools along the way.

For anyone embarking on an inquiry-driven expedition — whether it’s a research project, a service-learning program, or a self-designed summer of exploration — the labyrinth can serve as both metaphor and method.

Step 1: Glimpse the Center

Every journey starts with a vision, even if it’s fleeting. Write one sentence that captures your central purpose. For example:
“If my expedition does one thing well, it is…”

This is your north star, your “center.” Don’t worry if it feels fuzzy — clarity comes later.

Step 2: The Turn Outward

The labyrinth doesn’t take you straight to the middle; it pushes you outward first. That’s the part of the journey where doubt, unknowns, and questions surface. Ask yourself:

  • What don’t I know yet?
  • What feels unclear or intimidating?

Naming these uncertainties is not weakness — it’s the work. By acknowledging what’s missing, you create space to learn.

Step 3: Gather Your Tools

We rarely walk alone. Along the path, you’ll need tools — intellectual, relational, and practical — to carry inward. I like to divide them into four categories:

  • Conversations: mentors, peers, or communities to learn from
  • Concepts/Values: the principles that keep you aligned
  • Methods: research, mapping, storytelling, or observation techniques
  • Practices: reflection, rest, journaling, creative rituals that sustain you

Choose three to five. These will be your companions.

Step 4: Twists and Crossroads

No journey unfolds without barriers. Some are practical (time, funding, logistics). Others are external expectations — from family, institutions, or even society’s ideas about what you “should” do.

The regenerative approach isn’t to push through at all costs but to prepare alternate routes that still honor your purpose. Write a few if/then scenarios:

  • If not this location, then that one.
  • If not formal internship, then independent research or service.

Flexibility builds resilience.

Step 5: Return to the Center

Finally, revisit your original vision. With your tools, your unknowns, and your alternate paths in mind, rewrite it. Make it sharper, more grounded, more alive. You’re not back where you started — you’re back with new eyes.

Why the Labyrinth Matters

The labyrinth exercise is not about perfection. It’s about alignment. In regenerative leadership, we learn that when our values and our actions line up, our work nourishes us instead of depleting us. The labyrinth is a reminder that the path is rarely straight — but it is always meaningful.

So the next time you begin planning your inquiry-based expedition, don’t draw a checklist. Draw a labyrinth. Glimpse your center, name your unknowns, gather your tools, prepare your alternate routes, and walk with curiosity.

Because the truth is, the twists are not distractions from the journey — the twists are the journey.

For a short film exploring the labyrinth as guide, click here.

Learn, Unlearn, Relearn

 

This summer, I took part in the Global Citizenship Education course at the University for Peace (UPEACE), a United Nations–mandated institution dedicated to developing leaders who can build a more peaceful, just, and sustainable world. I am pursuing the Global Leadership Diploma through their Centre for Executive Education, and this was the second of five courses in that journey.

From the outset, I realized this course was different. It was not simply about learning the theory of global citizenship education (GCED). It was GCED in practice — modeled for us each week. Through interactive workshops, design-thinking activities, guest speakers, and sustained dialogue, we were not just studying global citizenship, we were living it together in community.

The most powerful dimension of the course was the exchange among participants from across the world. Each week we brought our lived experiences into the space: teachers, activists, administrators, peacebuilders, and learners representing diverse geographies, cultures, and perspectives. Theory never floated above reality; it was tested against stories from Ethiopia, Finland, Puerto Rico, Madagascar, Afghanistan, and beyond.

In that diversity, we were constantly reminded that everyone is both a teacher and a learner. This, for me, is the best part of UPEACE courses: the way they invite us into community, where knowledge flows in multiple directions and the classroom expands across borders.

Global citizenship education also requires unlearning: questioning the frameworks we inherit, recognizing Western-centrism and tokenism, and naming the power dynamics embedded in education itself. We explored empathy and cultural humility, critiques of soft GCE, and the tensions between local and global approaches.

These sessions challenged me to deepen the lexicon I use in my work. Words like empathy, humility, power, justice, accountability grew sharper in meaning through dialogue with others. Vocabulary is never just academic; it frames the way we act in the world.

At the same time, the course constantly turned us back toward practice. Weekly assignments weren’t afterthoughts; they were vehicles for integrating learning into our lives and work. Drafting vision statements, articulating challenge questions, and creating a personal manifesto pushed us to imagine how GCED might live in us as educators, leaders, or community members.

Here, GCED was not abstract. It was a lived pedagogy — a weaving together of head, heart, and hands. Knowledge and skills (cognitive), empathy and values (socio-emotional), and action (behavioral) came together.

If there is one reflection I carry forward, it is this: global citizenship is not a destination, but a cycle. To learn, unlearn, and relearn — again and again.

It sounds simple, but in practice it is profoundly demanding. To learn is to embrace complexity. To unlearn is to let go of frameworks and assumptions that no longer serve. To relearn is to weave new understandings into our lives and actions — anchored in justice, empathy, and sustainability.

Each turn of this cycle deepens our consciousness, sharpens our practice, and roots our commitments more firmly in care for both people and the planet. The lexicon expands, the meanings deepen, and we are reminded that global citizenship is not just something we teach, but something we become.

For me, the course also became a mirror for my ongoing work with The Geographical Imaginations Expedition & Institute (The GIEI). It sharpened my vision of how mapping, storytelling, and inquiry can move beyond “soft” global citizenship toward praxis — where ethos and action are inseparable.

This is the ongoing challenge: how to design learning expeditions that invite learners to see the world, and themselves within it, with renewed consciousness and responsibility. To keep cycling through learn–unlearn–relearn as a lifelong practice.

To the UPEACE team, my fellow participants, and our guest educators: thank you for creating a space that was equal parts challenging, compassionate, and inspiring. The course didn’t just teach global citizenship education — it modeled it, showing us what it can look like when lived in community.

The seeds we planted together will continue to grow, in classrooms, communities, and collaborations around the world.