On The Way To School

Are you winning, but withering?

You can be successful, dependable, and the person everyone turns to—and still be running on empty.

On today’s episode of On The Way To School, I’m reflecting on a message I heard from Dr. Dharius Daniels titled Winning and Withering. It reminded me of something we don’t talk about enough in leadership: you can be doing everything right on the outside while quietly running out ...

We’re familiar, but we’re not connected.

That thought has me reflecting on how we build relationships—not just with our students, but with the adults we work alongside every day.

Welcome to Season 10 of On The Way To School! After taking a little time to reset and get the school year into rhythm, I’m back with a question for all of us: How often do we choose what’s comfortable instead of making room fo...

This morning on On The Way To School, I’m reflecting on a conversation we had last night at Lore Leimert Park about the continuum of care—and a powerful question raised by Nikole Hannah-Jones’s recent writing about her daughter’s educational experience.

Parents make enormous decisions on behalf of their children.

We choose schools. We choose neighborhoods. We choose programs. We think about college. We think...

This weekend, I had the honor of returning to my alma mater, Concordia University St. Paul, and receiving the Alumni Association Educator of the Year Award.

I didn’t campaign for this one. I was nominated and selected. And that made the moment especially meaningful.

Standing there, I thought about the people who poured into me, challenged me, encouraged me, and helped me grow in the soil where I was planted.

That’s the ...

On today’s episode of On The Way To School, I’m thinking about what happens when significant changes are happening around our schools—and why thoughtful governance, legal guidance, and practitioner voice matter more than ever.

With proposed IRS and Treasury changes affecting tax-exempt organizations on the horizon, independent school leaders are asking important questions about compliance, governance, and how to p...

Dr. Chris Dennis discusses the hectic back-to-school season, the importance of honoring families' commitments to independent schools, and supporting teachers during long evening events. He emphasizes treating parents as partners and the value of community connections.

He also shares insights from his equity, justice, and leadership class about changing political rules of engagement and invites community experts into the classroom. ...

On today’s episode of On The Way To School, I’m thinking about resilience, independence, and what happens when we remove the structures that have surrounded our students for most of their lives.

We want our kids to be successful. So we organize. We supervise. We intervene. We advocate.

And often, we should.

But there are also moments when students need to experience some productive tension—to figure something out,...

In this episode Dr. Chris Dennis explains the Treasury/IRS proposal to strip 501(c)(3) status from private schools that use race-conscious policies in admissions, scholarships, athletics, or programming, and outlines the potential effects on up to 18,000 institutions.

He offers practical guidance for school leaders — inventory programs, align boards, prepare public comments, and communicate plans to employees and families &md...

On today’s episode of On The Way To School, I’m thinking about what happens during those first few days when new faculty are learning a school’s culture in real time.

They’re learning the policies. They’re learning the cues. They’re figuring out where there’s flexibility—and where there isn’t.

And they’re wondering: “Am I doing this right?”

That’s why the...

In today’s episode of On The Way To School, I’m digging into a question that deserves more attention in independent schools:

Are we looking at student retention from the wrong direction?

Research on faculty belonging and retention points to something we already know intuitively: educators are more likely to stay when they experience a healthy workplace culture, manageable workloads, meaningful relationships, and a genui...

Today on On The Way To School, I’m talking about the start of a new school year—and the opportunity it creates for educators and administrators to recast your own vision.

We spend so much time thinking about what students need when they return: new classrooms, new teachers, new routines, new friendships.

But what about us?

Who are you excited to reconnect with? Who is someone you don’t know well enough yet? What r...

It’s Monday, and On The Way To School is back in school mode.

In today’s episode, I’m looking at a recent development from the U.S. Department of Education’s Office for Civil Rights and what it may mean for independent school leaders and board committees working on equity, belonging, and discipline.

The bigger leadership lesson, though, goes beyond any one letter or policy:

When the rules change, don’t...

Dr. Chris Dennis opens the episode with warm-weather updates and a heartfelt response to the devastating flooding in Nepal, noting how technology amplifies shared empathy. He reflects on a moving faculty and staff Eucharist that affirmed the school’s Episcopal identity and its quiet but powerful role in community life.

The episode also celebrates the start of the school year—ninth-grade trips, chaperones, and the return...

When did you first feel like you belonged?

That question changed the conversation for me.

In today’s episode of On The Way To School, I’m reflecting on a question that came up during my recent Lonely Graduation book conversation on Martha’s Vineyard:

When did you first realize you were special?

For me, the answer came much later than I expected. It wasn’t until my 30s that I fully recognized my unique gifts ...

Today on On The Way To School, I’m talking about one of the biggest tensions I’m noticing as educators and leaders increasingly use AI:

The output can move faster than our thinking.

AI can help us research, organize, synthesize, build presentations, and get to a finished product in minutes. That productivity is real.

But sometimes the time we save is actually thinking time—the time we need to wrestle with an idea,...

When leadership gets thorny, go back to the policy.

In today’s episode of On The Way to School, I’m talking about an increasingly important reality for school leaders: sometimes the hardest leadership moments are the ones you never planned for.

Unplanned head-of-school transitions. Student incidents. Enrollment challenges. Family demands. Community pressure.

When the temperature rises, it can be tempting to become defen...

Healthy Boards. Healthy Schools.

We’re back. 🎙️ After a brief summer pause—and a great book conversation on Martha’s Vineyard—On The Way to School is back in gear.

In today’s episode, I’m digging into one of the most consequential relationships in independent schools: the board–head partnership.

Recent stories about schools facing serious fiduciary challenges, trustees being named in litig...

Sometimes the most powerful response is no response at all.

In this episode of On The Way to School, I’m talking about what happens when we’re triggered in difficult working relationships—and why we often need to process before we respond.

A simple practice has stayed with me for years: write it down before you say it.

Grab a notebook. A Post-it. A Google Doc. Write the sentence you want to say. Name what you&rsqu...

Dr. Chris Dennis returns for season nine with reflections on stepping back, recalibrating, and reclaiming joy by becoming a "tourist" in your own life and school. He shares the importance of revisiting what originally inspired you and highlights the launch of Jabali Academy as a source of community inspiration.

Tune in for a short, uplifting episode about renewing purpose, supporting new educational ventures, and embracing small pr...