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Eric Sheninger of Cypress on Life, Lessons & Legacy

Eric Sheninger shared their story and experiences with us recently and you can find our conversation below.

Eric, it’s always a pleasure to learn from you and your journey. Let’s start with a bit of a warmup: What do you think others are secretly struggling with—but never say?
As an author, speaker, consultant, and former principal, I’ve had the privilege of working with countless dedicated professionals in schools worldwide. What often strikes me, and what I believe many are secretly struggling with but rarely voice, is a profound sense of isolation and the fear of perceived failure when trying to innovate.

Think about it: many educators are passionate about transforming learning, embracing new pedagogies, or integrating technology in meaningful ways. They see the potential, they attend conferences, they read the research. But when they return to their schools, they often face systemic hurdles—lack of time, insufficient resources, an entrenched status quo, or even resistance from colleagues who prefer the familiar. This can lead to a feeling of being a lone wolf, fighting an uphill battle. They might be afraid to voice their frustrations or admit that their ambitious plans aren’t always unfolding perfectly because they fear being seen as incompetent, or worse, that their efforts will simply be dismissed.

Another silent struggle is the pressure to “do it all” and to be “perfect”. In education, there’s a constant stream of new initiatives, mandates, and expectations. Educators are deeply committed to their students, but this relentless pressure can lead to burnout. They might feel they can’t admit when they’re overwhelmed, when a strategy isn’t working, or when they simply need more support or time for professional growth. There’s a powerful narrative in education that equates struggle with weakness, when in reality, it’s often a sign of deep commitment and a willingness to push boundaries. We need to create cultures where vulnerability is seen as a strength, where asking for help is encouraged, and where the focus is on continuous improvement and learning from both successes and setbacks, rather than on achieving some unattainable ideal of perfection.

Can you briefly introduce yourself and share what makes you or your brand unique?
For over two decades, I’ve had the privilege of working in public education, first as an award-winning high school principal and now as the CEO of Aspire Change EDU.

My journey in education really took a significant turn when I became principal of New Milford High School in New Jersey. We were facing a lot of challenges, and it became clear that we couldn’t keep doing things the same way and expect different results. So, we embarked on a pretty radical transformation, leveraging digital tools and innovative pedagogies to improve teaching, learning, and overall school culture. We saw incredible results—improved student outcomes, increased engagement, and a much more vibrant learning environment. This experience truly shaped my philosophy: that innovation isn’t just about technology; it’s about reimagining what’s possible in education to better serve our students.

What makes my work through Aspire Change EDU special is our unwavering focus on impactful, sustainable change. We don’t just talk about innovation; we provide practical, research-backed strategies and support to help schools and districts actually implement it. We understand the complexities of real-world educational settings, and our goal is to empower leaders and educators to create equitable and engaging learning experiences for every student. We believe that true change comes from within, by fostering leadership and capacity at all levels.

Currently, a lot of my energy is focused on helping schools navigate the evolving landscape of education, particularly around areas like AI in education, personalized learning, and future-ready skills. It’s about preparing students not just for tests, but for a world that’s constantly changing. I’m passionate about sharing what I’ve learned and, more importantly, continuing to learn alongside the incredible educators I get to work with every day.

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What breaks the bonds between people—and what restores them?
In my experience, what most frequently breaks the bonds between people is a breakdown in trust and effective communication. When individuals or groups feel unheard, disrespected, or betrayed, the foundational elements of any strong relationship begin to erode. This can manifest as a lack of transparency, an inability to address conflicts constructively, a failure to follow through on commitments, or even subtle, unacknowledged resentments that fester over time. Differing priorities or a feeling that one person’s needs are consistently undervalued can also create significant rifts, leading to emotional distance and a sense of isolation even when physically present.

Restoring these fractured bonds requires intentional effort, empathy, and a genuine commitment from all parties involved. It begins with acknowledging the hurt and taking responsibility for one’s part in the breakdown, even if it feels small. Open and honest communication, focused on understanding each other’s perspectives rather than assigning blame, is crucial. This means actively listening, validating feelings, and being willing to be vulnerable. Consistent actions that demonstrate reliability and respect, along with a commitment to shared goals and a willingness to compromise, gradually rebuild trust. It’s about re-establishing a shared sense of purpose and a commitment to nurturing the relationship through mutual respect, forgiveness, and ongoing, empathetic engagement.

If you could say one kind thing to your younger self, what would it be?
If I could say one kind thing to my younger self, it would be this: “Embrace the messiness, and don’t be afraid to be vulnerable.”

Looking back, especially during those early days as a principal, I often felt an immense pressure to have all the answers, to project an image of unwavering confidence and control. I believed that showing any doubt or admitting to a struggle was a sign of weakness. What I’ve learned since then, through countless challenges and triumphs, is that true strength lies not in perfection, but in resilience, adaptability, and the courage to say, “I don’t know, but let’s figure it out together.” The most profound connections I’ve ever made, and the most significant growth I’ve experienced, have come from those moments when I allowed myself to be imperfect, to ask for help, and to lead with empathy and authenticity. I needed to ease up on myself. The journey is far more enriching when you allow yourself to be human.

Next, maybe we can discuss some of your foundational philosophies and views? Where are smart people getting it totally wrong today?
I’d say one major blind spot, ironically, is in their approach to change and innovation itself. Many intelligent leaders and educators recognize the urgent need for transformation – whether it’s integrating AI, personalizing learning, or developing future-ready skills. They can articulate the “why” brilliantly, backed by data and compelling narratives.

However, the misstep often occurs in the “how.” They might focus too heavily on mandates, top-down initiatives, or simply “selling” the idea of change to their staff, rather than fostering true ownership from the ground up. There’s a tendency to jump to solutions without deeply understanding the current context, the existing challenges of those on the front lines, or the psychological impact of constant new initiatives. We see this when brilliant tech solutions are adopted without sufficient professional learning, or when new pedagogies are introduced without creating the space and support for teachers to genuinely understand, experiment with, and adapt them to their unique classroom settings. The smartest people know what needs to change, but they sometimes underestimate the human element – the need for authentic collaboration, a culture of psychological safety, and a belief that the change is truly co-created and beneficial for everyone, not just an imposed directive.

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. How do you know when you’re out of your depth?
That’s a feeling every leader and innovator encounters, and it’s a critical moment for growth. For me, you know you’re out of your depth when you start feeling a sense of overwhelm coupled with a lack of clarity on the next steps. It’s not just that you don’t have the answer, but you don’t even know how to begin finding the answer, or you realize the scope of the challenge is far greater than your current capacity or expertise. This can manifest as a constant feeling of playing catch-up, making decisions reactively rather than proactively, or finding yourself unable to articulate a clear vision or strategy for moving forward. When I start to feel that intellectual and strategic paralysis, I know it’s time to pause, reflect, and re-evaluate.

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