by Richard Lemons, Jennifer Perry Cheatham, and Rydell Harrison
At our recent meeting of the Connecticut Superintendents’ Network, we found ourselves gathered around a familiar scene: a set of charts and graphs thrown up on the screen, lines bending and breaking, bars climbing and collapsing. Enrollment trends. Workforce data. Student learning results. Teen mental health. The future of college.
Someone finally named what many of us were feeling: It is very hard to lead a school system when the ground beneath schooling itself is shifting.
We were not just talking about the next budget cycle or the next bargaining round. We were wrestling with forces that are beginning to tear, and perhaps eventually reweave, the fabric of our society—and with the strange leadership assignment that comes with that: stewarding communities and schools in the here-and-now while lifting our gaze to a “then-and-there” that lives well beyond a five-year plan.
This piece is an attempt to name some of those forces and to sketch a few implications for system leaders—superintendents, state chiefs, trustees, presidents, cabinet members—who are trying to lead for the long now.
The world our young people are walking into
Across the analyses we reviewed, several themes kept surfacing—not as abstract ideas, but as curves on graphs that will show up in the lives of real children.
Unfinished learning and widening inequities. Post-pandemic academic recovery remains incomplete, especially in reading, and the burden is not equally shared. Gaps between low- and high-poverty districts, and between predominantly white systems and those serving mostly students of color, are widening. Chronic absenteeism has surged and, even with some recent easing, still slows recovery in many places.
A demographic and enrollment shock. Public school enrollment has fallen sharply since 2019–20, with millions of “missing students” no longer appearing in either public or private school files—and projections that even if families return to pre-pandemic habits, population decline alone will reduce K–12 enrollment for decades to come. If families continue to peel off toward homeschooling, virtual options, or pods, some systems will confront a world of under-enrolled schools, hard facility decisions, and funding formulas that lag reality—conditions that will land hardest in already-marginalized communities.
A youth mental health and belonging crisis. National mental health and social-support data make plain what educators feel in their bones: rising loneliness, anxiety, and a deep mismatch between how supported teens feel and how supported adults believe them to be. Schools are no longer asked only to deliver academic standards; they are one of the last shared spaces where young people can practice being human together.
The changing bargain of higher education and work. Confidence in the four-year degree has eroded. Fewer than half of adults now believe a bachelor’s is “worth it” without loans, and support plummets when borrowing is required. Meanwhile, satisfaction is higher among trade school graduates; apprenticeships and alternative credentials are growing; and workers describe a labor market that feels both tight and unforgiving, with skills that must be constantly refreshed. The old “default” pipeline—high school, four-year college, stable career—is no longer default.
K–12 systems under strain, responding unevenly. Trend analyses of districts across the country show systems trying to do many hard things at once: accelerate academic recovery, rebuild student engagement and mental health supports, adapt to volatile enrollment, develop and retain staff, upgrade data use, and align literacy practice with research—all while navigating new political pressures and governance norms. The job got harder; the stakes got higher; the toolkit is still catching up.
Layered on top of all this is the rapid evolution of digital technology, and especially AI. We kept circling back to a central tension: AI and automation are reshaping work, knowledge, and communication at an extraordinary pace, yet the core responsibility of schooling remains stubbornly human—to help young people learn to think, discern, relate, and contribute.
Technology, in this view, is not destiny; it is an amplifier of whatever social and institutional choices we make.
What we heard in the room
Our conversation did not focus only on trends; it kept returning to how these forces land on actual children and families.
Superintendents spoke about the ways declining enrollment, unfinished learning, and mental health challenges fall hardest on students who already sit at the edges of our systems—young people navigating poverty, racism, disability, unstable housing, or family trauma. We asked: Who is most exposed as these trends converge? Who is most buffered?
We talked about support systems: the web of relationships, community partnerships, and public services that must surround young people if they are to thrive in this environment—and about how thin or fragmented that web has become in many communities.
We surfaced some of the orthodoxies that shape our work—what we fund, how we schedule time, what we treat as “real” learning, how we sort and label students, what futures we implicitly present as desirable. Those givens, we agreed, will have to be interrogated, not simply taken for granted, if our systems are to meet the moment.
We also named a central leadership tension: superintendents are responsible for managing the current system in communities that are not necessarily asking for a revolution. At the same time, they are expected to lay the groundwork for transformations that may not bear fruit during their tenure—or even in their lifetime. If they do not place those long bets now, though, improvement keeps getting pushed down the road, and the system falls further out of sync with the world our students are entering.
That tension led us into larger questions:
- What is public education for in this era?
- What forms of learning will young people need in order to flourish amid volatility, polarization, and technological acceleration?
- How do we build stronger supports for our most vulnerable students and families, not as charity but as a matter of justice and long-term societal health?
- How do we help those outside our schools—voters, taxpayers, skeptics, families who are leaving us—better understand what we are actually trying to do, even as we try to better understand their motives, frustrations, and hopes?
Here, the adaptive leadership theory of Ronald Heifetz offers both caution and invitation. Many of the challenges we face cannot be solved by technical fixes alone. The leader’s task is to create a container—a holding environment—in which a community can face hard truths, name competing values, and begin its own work of reimagining the purpose and form of schooling. That means framing the real issues at play, resisting the temptation to offer premature answers, and deliberately handing the work back to “the people” who must ultimately own both the diagnosis and the path forward.
Different mental models, different futures
One theme of our discussion was the recognition that different stakeholders view this same landscape through very different lenses.
For many policy elites, pundits, and funders, the conversation has migrated toward “systems transformation,” disruption, and choice. The questions sound like: What if we redesigned schooling from the ground up? What if we unbundled learning from schools altogether?
For many parents currently raising children in public schools, the questions are closer to home:
- Is my child safe and known?
- Are they learning the basics?
- Will they have options when they graduate?
And for students themselves, especially those furthest from opportunity, the questions are more visceral still:
- Do I belong here?
- Does any of this relate to the life I want?
- Can I imagine a future where I am not always on the back foot?
Superintendents live at the intersection of these mental models, sitting with boards elected in polarized environments, parents managing day-to-day realities, educators carrying both hope and fatigue, and young people whose futures are being shaped in real time.
No wonder it is hard to hold the near and the far in the same field of vision.
What leadership requires in this moment
Our conversation did not produce a checklist. It did, however, point toward several leadership stances that feel increasingly non-negotiable.
- Hold multiple time horizons at once.
Leaders will continue to face acute short-term pressures—staffing, budgets, safety, politics—even as they are called to redesign systems for a very different future. The work is to resist the pull toward either crisis-only leadership or dreamy futurism. Instead, it is to move among three horizons:
- The urgent now: What must we do this year to keep students safe, learning, and connected?
- The decade arc: How do we redesign our systems so that a child entering kindergarten today experiences a coherent, opportunity-rich K–12 journey?
- The generational horizon: What choices are we making—or failing to make—that will shape who still trusts and uses public education 20–30 years from now?
- Rename “foundational skills” for the age we are in.
The reports on workforce and higher-education trends suggest that the foundation young people need is shifting. As one superintendent noted, reading and writing may be only a portion of the new literacies demanded to thrive in a modern world. But long-term flourishing will likely depend on capacities such as listening, speaking, learning new tools over a lifetime, collaborating across differences, discerning truth in noisy information environments, managing one’s own attention and emotions, and persisting amid ambiguity. These are not “extras.” They must be developed through rich academic work, not tacked on at the margins.
- Put belonging and relationships at the center, not the edges.
The youth mental health data—and what we hear from students—make clear that connection and belonging are not “soft” concerns; they are essential infrastructure. Leaders can insist that every student is well known to at least one adult, redesign time and space for advisory and mentoring, and push back against schedules and policies that unintentionally erode relationships in the name of efficiency.
- Put the most affected students at the center in an era of divergence.
Across nearly every data set we reviewed, the same pattern appears: the forces destabilizing education—declining enrollment, unfinished learning, absenteeism, mental health, skepticism about college—fall hardest on already vulnerable populations. Educating all our students requires asking hard questions: Which students are we assuming will stay with us, no matter what, and which are we implicitly treating as expendable? How are those who have historically been “done to” being brought into shaping the reforms that are ostensibly for them? What orthodoxies—about attendance, grading, discipline, pathways—need to be revisited in light of our most vulnerable students’ lived realities?
- Build futures literacy and containers for adaptive work.
Rather than pretending we can predict the future, leaders can help their communities become more literate about possible futures and more capable of working on them together. That might mean simple scenario-planning exercises with boards, bringing student and parent voices explicitly into conversations about technology and school design, or creating standing structures—cabinet conversations, community forums, networks like ours—that regularly surface weak signals and stress-test assumptions.
In terms articulated by Ron Heifetz and colleagues in their work on adaptive leadership, this is the work of building a holding environment: a space where a community can stay with the heat of change without fleeing to denial or scapegoating, and where the work of reimagining schools is shared rather than hoarded.
The goal is not to eliminate uncertainty; it is to build the muscle to navigate uncertainty together.
Chin up, feet planted
As our meeting drew to a close, the charts were still on the screen. Nothing had magically resolved: the enrollment lines still sloped downward in some regions, the absenteeism graphs still spiked, the mental health data still made our stomachs tighten.
But there was also something else in the room: a sense that we were not carrying this alone.
System leaders today are often asked to be both chief executive officer and chief futurist for their communities. That is an impossible job if approached in isolation. It becomes slightly more possible when leaders gather, share what they are seeing, test their mental models against each other’s, and dare to ask:
Given all of this, what kind of future do we want to make more likely for the children in our care? And what small, concrete bets can we place now to move in that direction?
Leading for the long now requires exactly that stance: chin up, taking in the horizon; feet planted, doing the next right thing for students and staff today.
My hope is that spaces like the Connecticut Superintendents’ Network—and the many leadership tables you sit around—can continue to be places where we practice that stance: where we help each other see the tearing of the social fabric clearly, and participate, with as much wisdom and courage as we can muster, in its reweaving.
In Partnership,
Richard Lemons, Jennifer Perry Cheatham, and Rydell Harrison
Key Readings Shaping Our Conversation
If you are looking to dig more deeply into the forces named above, consider starting with these pieces:
- Pivoting from Pandemic Recovery to Long-Term Reform: A District-Level Analysis
Dewey, J., et al. (2025). Pivoting from pandemic recovery to long‐term reform: A district-level analysis (Education Recovery Scorecard Technical Report). Education Recovery Scorecard.
District-level look at post-pandemic achievement, chronic absenteeism, and the uneven pace of recovery—and what it means to move from short-term “recovery” to long-term system reform. - Declining Public School Enrollment
Council, D., Goulas, S., & Monachou, F. (2025, August 27). Declining public school enrollment. Brookings Institution.
Explores demographic shifts, pandemic-era “missing” students, and long-run projections that suggest profound implications for school funding, facilities, and system design. - Most Americans Feel Good About Their Job Security but Not Their Pay
Lin, L., Horowitz, J., & Fry, R. (2024, December 10). Most Americans feel good about their job security but not their pay (Pew Research Center Report). Pew Research Center.
Analyzes how U.S. workers think about job security, wages, and changing skill demands—context for rethinking what it means to prepare young people for a volatile labor market. - Key Labor Force Trends (chapter excerpt from the above Pew report)
Fry, R., Lopez, M. H., & Keegan, T. (2024, December 10). Key labor force trends. Pew Research Center.
Provides the charts on unemployment, job tenure, earnings, and workforce composition that underpinned our discussion of the changing “bargain” between education and work. - 2025 Higher Education Trends
Clark, C., Cluver, M., Fishman, T., & Kunkel, D. (2025, April 7). 2025 U.S. higher education trends. Deloitte Insights.
Identifies major pressures on higher education—including questions about the value of the four-year degree, the rise of alternative pathways, shifting risk landscapes, and the need for new forms of “systemness” in the sector. - 2025 Trends in K–12 Education
Hanover Research. (2025, January 29). 2025 trends in K‑12 education. Hanover Research.
Synthesizes six national trends—from uneven academic recovery and enrollment volatility to new approaches to student support, staffing, data use, and literacy reform. - “U.S. Teens Need Far More Emotional and Social Support”
American Psychological Association. (2025, April 1). U.S. teens need far more emotional and social support. Monitor on Psychology.Reports on rising loneliness, gaps between teen and parent perceptions of support, and the mental and physical health consequences—underscoring why belonging and relationships must be treated as core infrastructure, not enrichment.
