This article appeared as "Moment of Clarity" in the Winter 2025 issue of Independent School.
“Trends are always forming, but it feels like there is something different about this particular moment in time,” said futurist Amy Webb during her most recent and much-anticipated talk at the 2024 South by Southwest (SXSW). “I’ve modeled it, I can see it, and my hunch is that a lot of you sense that something about this moment is different too.”
Webb, cofounder and CEO of the Future Today Institute (FTI), which focuses on trends in the technology sector and their impact, went on to describe the profound societal transition that we are experiencing, one so massive that she refers to everyone alive today as “Generation T,” the generation in transition. In FTI’s “2024 Tech Trends Report,” released at SXSW, Webb and her colleagues describe society’s entrance into a technology supercycle, a “wave of innovation so potent and pervasive that it promises to reshape the very fabric of our existence, from the intricacies of global supply chains to the minutiae of daily habits, from the corridors of power in global politics to the unspoken norms that govern our social interactions.”
As school leaders try to imagine the future our students are stepping into and ensure that they’re providing a relevant education amid these conditions, they must also confront the unexpected and complex responsibilities that await them. Schools were built for a time that no longer exists, and school leaders must widen their perspectives from the constant and specific demands they’re facing to consider bigger questions—much bigger questions to really get them thinking about how to create a more just, relevant, healthy, and sustainable education experience. Questions like “What is success?” “Are we OK?” “Who is unheard?” and “What is our legacy?” should become critical guideposts for school leaders as they plan for the future. This kind of planning requires new skills and dispositions and a shift in how we think about planning itself.
Our Liminal Moment
Consider how a caterpillar turns into a majestic monarch. The butterfly’s story of transformation is not unlike what Generation T is experiencing, particularly the ugly in-between—that period when the caterpillar goes into its protective shell, hidden from view, twisting, struggling, and growing within a confined space that gets harder and harder over time. Similarly, in our lives and at schools, we’re all struggling to make sense of this in-between moment, when old ways of thinking about the world are breaking and new stories are yet to be written. Scientists call this a “liminal” moment, when we feel the loss of the old, but we’re not sure yet what the new will be.
Many of the ways we understand and operate in the world are failing us—old narratives around media, politics, relationships, earning a living, and, yes, education, are increasingly breaking. For instance, social media have upended the way we consume and create the news, allowing influencers without traditional credentials to gain large followings and impact. Trust in institutions is at an all-time low everywhere we look. The traditional story of “success” and how we attain it is increasingly irrelevant.
While we might be living in a period between clashing worldviews, a global consensus around where schools need to go is forming: toward an education that is more relevant, just, and healthy for all. Too much of what’s currently taught in schools has little immediate application to students’ modern lives and is a remnant of a time when content, knowledge, and information were scarce. In addition, while increasing numbers of schools are keen to discuss expanding student agency and the inclusion of more diverse voices in conversations about the school experience, the gap between rhetoric and practice remains wide. And as numerous studies point to physical, mental, and emotional challenges for youth worldwide, few schools have increased emphasis on spending more time in nature, understanding the deep importance of diet and exercise in well-being, and helping students grapple with the stresses not only of schooling but of a quickly changing world filled with potentially addictive technologies.
To realize any of this, we need to ask questions that anchor a school’s strategic process, ones that stir the conversation around the kind of education schools are providing and the long-term outlook for future generations, questions such as “Who are we now?” and “Who do we want to become?”
Pushing forward won’t be easy and, at times, might even be painful when we consider everything that must be shed to emerge from the messy middle. But not everything must be discarded. Remarkably, in the chrysalis-to-butterfly metaphor, the insect carries memories within itself into each phase of life. The same can be true with schools.
Fearless Inquiry
It’s no surprise that those who are trying to plan for even the near future are quickly shifting to a different approach. In 2020, school leaders learned that a sudden disruption like a pandemic can throw the most thoughtful plans into chaos. Racial and social justice imperatives, economic uncertainty, wars, political polarization, and a looming climate emergency are also teaching us that strategic planning for three or five years into the future is becoming not just more difficult but more impractical. So how can schools design an educational experience to be sustainable? As we have seen among the independent, public, and international schools that we work with, embracing the uncomfortable, messy, uncharted territory calls for a focus on possibilities to be uncovered rather than certainties to be recovered.
Our starting point for this work is the 12 Big Questions, designed to support school leaders to ask the challenging (yet deceptively simple) questions that will help them move through the uncertainty and plan for the future. We created this list with an eye toward helping them not only to understand more deeply what is happening in their schools in this current moment but also to develop aspirational answers that help them imagine the school experience they want to create moving forward.
These questions also help school communities focus on sustaining what is most important in their work, as well as move them to think about what the Royal Society of Arts calls “regenerative futures,” which are focused on rethinking our roles, restoring those practices that align to our most deeply held beliefs, and replenishing the energies and dispositions that are needed for the work ahead.
Many of the schools that have used these questions have chosen the ones they find most relevant or interesting. Others have convened community groups of students, teachers, parents, and others to work through all of the questions to help them build shared understanding, shared language, and coherence in their work.
Through many conversations with thousands of educators and leaders around the world, we found that the following 12 Big Questions cover the range of important contexts and challenges that schools must address in order to be sustainable and relevant through changing and uncertain times.
What is sacred?
What is learning?
Where is the power?
Why do we _____?
Who is unheard?
Are we literate?
Are we OK?
Are we connected?
What’s our story?
What is success?
What’s next?
What is our legacy?
Notice that none of the questions start with “How.” Research and experience show that the answers to the “How?” questions, as in “How do we design a process for reimagining our classrooms?” or “How do we articulate an updated mission?” lie within each school community’s capacity to discover their “Why?” and “What?” as a reflection of grappling with these bigger questions.
Strategy for Tomorrow
Using these questions, schools can create aspirational and attainable visions for what schools must become. Zachary Stein’s 2019 book Education in a Time Between Worlds: Essays on the Future of Schools, Technology, and Society presents it this way:
Those preoccupied with fixing the existing system of schools do not stop to ask questions about what schools are for, who they serve, and what kind of civilization they perpetuate. As I have been discussing, our civilization is in transition. … This is the task of education today: to confront the almost unimaginable design challenge of building an educational system that provides for the re-creation of civilization during a world-system transition. This challenge brings us face-to-face with the importance of education for humanity and the basic questions that structure education as a human endeavor.
Some may find Stein’s conclusions extreme or, at minimum, uncomfortable. But the reality is that schools were built for a time when information, knowledge, teachers, and technologies were scarce; when the challenges were not as numerous, complex, or existential. Today our “normal” ways of doing things, both inside of schools and in the larger society, have brought us the challenges we now face.
In 2022, education leaders around the world, led by the United Nations Educational, Scientific and Cultural Organization (UNESCO), agreed that it’s not about making our current systems and practices “better.” Instead, we need to think fundamentally differently about the experience of school that we must now create for students in the near future—a new social contract or, in Stein’s words, “education for humanity” and the flourishing of all living beings.
Designing for the Future
We use a simple frame to guide schools as they explore the big questions: “Face reality. Imagine harder.” This statement acknowledges the contexts and stories impacting schools and offers a challenge to unstick the thinking and creativity that drive the work of a school. It might lead schools to ask, “How can we design for future learning environments if we haven’t asked and arrived at some coherent answer to the question ‘What is learning?’” “How do we design for success if we haven’t defined what we believe success should be in the future?” “How do we design for agency if we’re not sure where current power relationships exist?” “How might we realize justice and equity if we haven’t assessed ‘Who is unheard?’”
When we shift the outcome of the questions to “designing for,” we maintain clarity around the “why” of each question and avoid falling into tactical rabbit holes or arguing about details. Such a deliberate inquiry process helps reveal solutions that are clarifying, inclusive, and future oriented.
When we worked with faculty and leadership at Green Vale School (NY) in conjunction with their strategic plan rollout during 2022–2023 and 2023–2024, the Big Questions helped build shared understanding within teams and across roles, clarify implementation, and even make space for aspirational thinking and imagination connected to their goals and hopes for the future. The inquiry and design process led to developments such as more widely and meaningfully integrated learning for global competence even among the youngest students, and the start of an ambitious center dedicated to teacher excellence with a futures orientation.
At the Mount Vernon School (GA) in 2022–2023, faculty, staff, board members, and learning leaders used the 12 Questions as a jumping-off point to consider possible futures. “The questions urged us to ask even more questions, further our research, and design an exciting journey of ‘How Might We?’” according to Head of School Kristy Lundstrom. Many of their conversations informed the publication of Mount Vernon’s Spring 2024 Transformation R&D Report, “Imagine Then, Act Now: Futures Literacy for Learning Organizations.”
Dispositions and Skills for a New Era
Amid accelerating uncertainties, strategic planning requires school leaders to take on key dispositions, such as fearless inquiry, that get baked into the school’s culture and, eventually, into its DNA. In his 2022 Harvard Business Review article, “Strategy in an Age of Uncertainty,” Nathan Furr highlights how uncertainty—like inquiry—is an area few leaders are trained in, even though that is the gateway to all growth, change, and transformation. “We have to go through the uncertainty to get to the possibility.”
This is where strategy, design, and mindsets intersect. These dispositions are teachable, and they help create a strategic planning process that’s more robust, lasting, and inclusive. They include the following:
An explorer’s mindset: Author and consultant John Hagel writes extensively about this disposition, as explorers enter unknown territory, seeking new vistas (possibilities), equipped with tools that help them shine light in the darkness and navigate challenges, while maintaining humility amid fearlessness and vulnerability.
Hope: As educator and activist Mariame Kaba teaches, “Hope is a discipline. It is a commitment to the future that must manifest action.” As educators, we are futurists, but our work is not rooted in an empty optimism or toxic positivity. Our hope is fueled by research, action, a sense of belonging, safety to iterate, and, most of all, the lives we directly impact.
Radical acceptance and radical imagination: Radical acceptance happens when we see things as they are, not as we wish they might be, and listen deeply, with humility and curiosity, to diverse (and often difficult) truths. Radical imagination helps us visualize and create the world we want to build—to stretch our thinking across all aspects of the school experience. These dispositions accept that mistakes will be made and have the potential to advance learning while we imagine the futures for which we yearn.
Sense-making: Pervasive uncertainty makes learning how to conduct sense-making vital. Distinct from “learning” or “understanding,” sense-making involves “structuring and articulating the unknown by creating an emerging picture that becomes more comprehensive through data collection, action, experience, and conversation,” particularly across opinions and perspectives that differ from one’s own, as Deborah Ancona from MIT’s Sloan School explains.
These skills and dispositions get to some of the profound “inner work” required for sustainable and systemic change. A growing chorus of experts have realized that “outer” (including organizational and social) development is not sustainable without developing profound “inner” capacities. Thus, a movement for Inner Development Goals (IDGs) has emerged. Co-created by more than 1,000 scientists, experts, and HR and sustainability professionals from around the world, the IDGs serve as a roadmap for developing the inner capacity to deal with the complex challenges faced by our Generation T.
Amid the uncertainty, doubt, and complexity of this moment in history, clear answers that will sustain schools to serve the real needs of children and survive as institutions are difficult to come by. Traditional strategic planning isn’t enough. Technical fixes to curriculum, assessment, or business development won’t save us. Designing an experience of school that is more relevant, just, healthy, and sustainable calls for courage and fearless inquiry into challenging questions—questions that get to our core beliefs as humans, that call for leaving behind practices that no longer serve schools or the world we are in, and that truly listen to the experiences of all the voices of our wide-ranging communities. As the Generation in Transition, to confront the most challenging questions and engage in creating new systems and practices, we need to do the inner work—the shifts in mindsets and dispositions that have the power to create a new story of schools—to emerge with truth, beauty, and goodness out of our liminal moment.