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 r...

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 ro...

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 colleg...

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 w...

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, governa...

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 com...

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 figu...

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...

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 first couple of weeks are so important. Do...

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 rel...

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 e...

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,...

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, cha...

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 un...

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 wres...

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 t...

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 litigation, a...

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. N...

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 education...

Dr. Chris Dennis walks through how school leaders can prepare in August to launch a steady school year: setting meeting cadences for direct reports, prioritizing classroom time (his goal is 25%), and staying present with faculty, students, and families. He shares practical tips—short classroom visits that aren’t evaluations, morning drop-off greetings, balancing teaching and advising, and building...

Dr. Chris Dennis delivers a short drop-in episode on why equity work must be embedded in school board governance rather than treated as an add-on. He outlines practical steps—linking equity priorities to accreditation and core board functions—to make DEI durable, and offers to share resources for trustees ready to operationalize this work.

On the Way to School with Dr. Chris Dennis closes out May with a heartfelt message celebrating educators and administrators for making it to the final week, reflecting on a holiday of remembrance and a sermon about the price of success. Chris highlights that success often comes from mundane, daily commitments—showing up, persevering, and honoring small acts of dedication—and urges listeners to aff...

Dr. Chris Dennis opens this episode with Memorial Day reflections, honoring those who served while sharing a lighthearted community story about an epic Continuous Uno game. He then shifts to school leadership advice: use the quiet review week to plan and prepare for a productive summer so your fall can be calm and focused. Finish May strong and take time to rest and appreciate your community.

In this episode Dr. Chris Dennis discusses a Forbes article outlining five signs a leader may need executive coaching—tolerating visible low performers, high performers burning out or quitting, lack of promotions, defensiveness when challenged, and teams afraid to speak the truth. He explains how coaching supports better change management, accountability, and retention, and encourages educators to...

Dr. Chris Dennis shares a morning anecdote about reconnecting with a former student and a mentor's advice: "Between 9 a.m. and 7 p.m., your ideas belong to your employer—after 7 p.m., they're yours." The episode encourages educators to protect their private time, pursue personal goals, and be accountable to their own timelines instead of letting work hours consume creative energy.