I stepped away from a Headship without knowing where I was going next.

It’s not the kind of move Heads of School are encouraged to make. Our profession tends to reward forward motion — title to title, role to role — with little pause in between. When I announced I was leaving my previous headship, I could sense the unspoken questions: So… what’s next?

The honest answer was that I didn’t know yet, and I was okay with that.

I didn’t frame it as “unemployment” or “in transition.” I called it what it was — a career sabbatical. Not a vacation. Not a break. But a sacred space carved out between roles to deepen, stretch, and recalibrate. A year of living with intention, if not with an official title. I wasn’t checking out of education; I was stepping further into it by other means. 

I had spent years in school administration, crafting strategic plans, managing crises, mentoring staff, and pouring everything I had into communities I loved. That kind of leadership comes with a cost, and it often leaves little room for reflective growth. I realized that if I didn’t stop and reclaim that space for myself, I risked becoming a leader with more habits than vision. I didn’t want to run on fumes; I wanted to return to school leadership with a fuller soul and sharper clarity of purpose. 

So, I gave myself permission. Permission to rest, but more importantly, permission to wonder.

My Time Away

I coached high school football and middle school hockey. I even coached a girl’s field hockey team despite effectively knowing nothing about the sport. I volunteered in support of at-risk youth. I picked up consulting projects. I created an LLC, which allowed me to partner with schools in ways I hadn’t before. I launched a campaign for my local school board. I withdrew from that campaign and threw my support behind three exceptional women who had previously been my opponents. I read obsessively. I wrote more. I explored new questions that had long lived at the edges of my professional consciousness. Most importantly, I searched for places where I could make a larger impact on children who needed it most.

I found myself drawn back, again and again, to kids. I was newly astounded by their needs, their brilliance, and their resilience. I sat in classrooms not to evaluate but to witness. I joined conversations not to direct but to learn. I listened more than I talked. And I began to dream about a different kind of leadership. Not more ambitious, not more decorated, but more grounded.

That year turned out to be one of the most productive and meaningful of my career.

A New Role

It made me brave enough to say yes to my current role at Cornerstone Christian Academy, a K-8 school in Southwest Philadelphia serving primarily students of color, many from historically underserved families. We provide scholarships that cover an average of 90% of the cost of attendance. We strive to form children academically, spiritually, and morally. It hasn’t been an easy job, but it’s been the right one.

I arrived with fresh eyes. I saw the mission clearly. I had energy to spare. I was hungry to serve, not out of obligation, but out of renewal. I wasn’t burned out. I was lit up.

That clarity came at a cost, not of money, but of ego. A career sabbatical feels countercultural in a field that values nonstop striving. I had to make peace with the discomfort of slowing down while others surged forward. I had to explain to myself repeatedly: No, I haven’t left education. No, I don’t have a role lined up. Yes, this is intentional. I had to trust that investing in my growth without a guaranteed outcome was still a worthy investment.

I don’t think I’m alone. I’ve met many other seasoned, wise, and accomplished Heads who quietly whisper their longing for a pause. They want time to write that book, visit that school in Helsinki, or sit with students without checking their phones. But they’re afraid. Afraid of falling behind. Afraid of losing their edge. Afraid of what people will think.

To them, I say this: take the sabbatical. If you have the means, create the margin. Reframe the gap not as absence, but as formation. Do things that confuse the search consultants but delight your soul. Coach a sport. Mentor a new leader. Start a podcast. Shadow a student. Spend a month in silence. Go deep into your community. Do something that makes you feel, again, what you once felt when you first fell in love with schools.

Nonlinear Growth

One of the most honest things you can model for your community is the fact that growth doesn’t always happen in a straight line. That leaders are learners. That risk-taking is not just for students.

In a field that loves its momentum, there is radical power in saying: I’m going to stop, reflect, and choose my next step with care.

When I finally stepped back into Headship, I came back not just as a more experienced leader, but as a more grounded one. Less performative. More present. Less interested in the optics. More invested in the people.

In other words, I came back as someone I recognized, and someone my school needed.

I’ll never regret it.