On The Way To School

Dr. Chris Dennis discusses how to respond when you’re passed over for an opportunity—encouraging self-reflection, identifying fixable truths from the process, and seeking coaching to recover. He offers personal examples and practical steps for educators and administrators to regain perspective, learn from the experience, and prepare for future opportunities.

Dr. Chris Dennis breaks down three practical strategies for educators entering the job market: work with a coach to prepare, aim higher than the obvious next step, and use warm introductions to build trusted connections. He also offers to connect listeners with coaching referrals and gives quick guidance on presenting a positive narrative during interviews.

Dr. Chris Dennis shares a quick, practical guide to returning after spring break with three simple steps: prepare your week, process what the break meant to you, and make room for play. He discusses how to recalibrate your focus as a leader, offers upcoming episode topics like job hunting, and reflects on the launch of Lonely Graduation.

Dr. Chris Dennis recalls the whirlwind launch week for his new book, Lonely Graduation, from a packed Leimert Park bookstore event to campus talks at Hamline University and a bestseller debut on Amazon. He shares highlights from launch events in Los Angeles and Minneapolis and reflects on the community response and social proof of the book’s message. Chris outlines three practical takeaways: momen...

Dr. Chris Dennis returns with a short update: apologizing for a missed episode, celebrating spring break, and encouraging educators to rest and recharge. He announces the launch of his book Lonely Graduation (March 24) and related events in Los Angeles (Mar 25), Hamline University (Mar 26), and Minneapolis (Mar 27), and reflects on the rewards of independent publishing and taking small steps to ma...

Dr. Chris Dennis shares episode updates on the March 25th Lore Bookstore signing in Los Angeles and the March 27th Strive Bookstore event in Minneapolis as Lonely Graduation approaches. He celebrates a student pitch contest that showcased creative, real-world solutions and encourages educators to nurture their own passion projects as spring break approaches. Practical reminders include adjusting t...

Dr. Chris Dennis opens the episode with book launch news and podcast milestones, then shifts to a practical conversation for educators on the importance of lesson documentation. The episode explains why a clear scope and sequence, written lesson plans, and updated records help with student assessment, substitute teaching, and administrator inquiries — and encourages teachers to carve out time to s...

Good morning — Dr. Chris Dennis counts down 21 days to the release of Lonely Graduation, shares a workshop anecdote where the book inspired someone's next academic step, and invites listeners to pre-order a signed copy for the March 24 release. He reflects on a meaningful weekend with a gospel concert and a family gender reveal, encourages educators to prioritize rest during the busy semester stre...

Dr. Chris Dennis reflects on the unglamorous but essential work of conflict resolution and mediation in schools, emphasizing the value of preparation, de-escalation skills, and calm leadership when challenges arise. He also shares personal reflections about slowing down, connecting with community, and balancing the demands of leadership with self-care and human connection.

📍 30 days out from Lonely Graduation. And today I’m thinking about proximity. Had lunch with a friend I’ve known since 2007. He still had a picture on his phone from when he visited me at a school where I worked years ago. That hit me. Because your career isn’t just built on titles. It’s built on moments. On how people experienced you. Yesterday, someone told me: “It’s not about who you know. It’...

Dr. Chris Dennis discusses how educators and administrators should handle reference checks with honesty and integrity. He advises sharing areas for growth in an asset-based, actionable way that supports the candidate and helps hiring teams make informed decisions. The episode covers formal and informal references, the importance of face-to-face feedback when possible, and the responsibility of ref...

Host Dr. Chris Dennis opens with reflections on a moving Black History Month high school chapel and then explores the value of humility and self-criticism for educators. He describes how reflective, humble leaders quietly make big impacts, accept feedback, and keep improving without needing the spotlight. This episode offers a brief, encouraging look at how self-awareness and thoughtful critique c...

Dr. Chris Dennis shares updates on his book Lonely Graduation, thanks listeners for pre-orders, and recounts presenting at SoCal POSIS’s Bring POCC Home event. He reflects on community, networking, and the power of affinity gatherings in independent schools. He also summarizes a keynote by Dr. Rodney Glasgow about treating your spaces—home, classroom, office—as sacred places to be grounded, restor...

Dr. Chris Dennis welcomes listeners to a rainy Thursday episode focused on mid-year pressures in schools. He discusses preparing for and recovering from intense meetings, using deep breaths and contemplative silence to reset, and the importance of maintaining good self-care practices. He encourages finding small moments of joy, even dancing at home, to celebrate progress and stay connected to the...

Host Dr. Chris Dennis reflects on a brief middle-school Harkness discussion he observed, highlighting how students engaged with The Skin I'm In and moved into deeper dialogue. He connects that classroom moment to leadership: meetings work best when everyone arrives with the same content and preparation, enabling informed decisions. A concise reflection for educators and administrators about studen...

Dr. Chris Dennis reflects on recent events—from the passing of Reverend Jesse Jackson to a trip to Montgomery and a talk by Bryan Stevenson—and highlights the power of proximity in understanding equity, justice, and the humanity of those most impacted. The episode urges school leaders and educators to spend more time in classrooms (including commitments of 50% or 25% time), outlines plans to suppo...

📍 Eight days. Three cities. Three powerful gatherings. Minneapolis. Montgomery. Atlanta. I'm back home; grateful, tired, recalibrating. This week reminded me how important it is actually to engage when you're at conferences. Don't just sit with those you know. Not just anchor to what's comfortable. But introduce yourself. Pour into someone. Learn from someone. Take the selfie. Send the text. Buil...

Dr. Chris Dennis describes his visit to the Legacy Museum and related sites in Montgomery, Alabama, reflecting on the history of enslavement, reconstruction, and the link to present-day mass incarceration. He shares emotional moments from the exhibits, the personal impact of confronting this history, and a renewed call to activism and supporting incarcerated voices. He encourages educators to visi...

On this episode of On The Way To School, Dr. Christopher Dennis records live from Montgomery, Alabama during the NAES EIJ conference as he visits the Legacy Museum, the National Memorial for Peace and Justice, and the Freedom Monument Sculpture Park. He shares personal reflections on confronting 400 years of history—from enslavement and segregation to mass incarceration—and the importance of immer...

Welcome to another episode of On the Way to School. Dr. Dennis records from Montgomery, Alabama, during the National Association of Episcopal Schools Equity and Justice Conference and reflects on a recent visit to Minneapolis, where he led a discussion at the Kente Summit about the book "Lonely Graduation." Students from local colleges shared honest stories about the fade of applause after achieve...

In this episode, Dr. Dennis connects with Dr. Roger Bridges of Building Bridges Consulting, who obtained his doctorate in leadership from USC, and recounts a career that began working with vulnerable youth in residential treatment and grew into roles at independent schools like Branson, Windward, and Echo Horizon. Their path led to consulting work focused on bridging wellness and belonging across...

In this dual episode, Dr. Chris Dennis and guest host Rob Evans of the Just Curious Podcast discuss what it means to serve in education, exploring joy, humility, and the awe that comes from mentoring, building programs, and supporting students and colleagues. They share personal stories, name mentors and unsung heroes, and invite listeners to reflect on how service can be a blessing, not a burden,...

Host Dr. Chris Dennis celebrates his birthday with a short episode, reading page 44 from his upcoming book Lonely Graduation: The Journey After the Milestone. He introduces a section called "The Conveyor Belt of Achievement," which explores how continuous striving can overshadow the ability to honor and process success. The book is available March 24, with pre-sales open now.  After the reading, C...

Today I caught myself thinking about something we all do, but rarely admit: disengaging. You know the moment. You’re in a meeting. Your mind is somewhere else. You’re tired, frustrated, distracted, or just over it. Your body is there, but your energy isn’t. And slowly, you start to disappear from the room. In today’s episode, I challenged myself and you not to default to disengagement. Because dis...

S10 E162 📍 This Monday had me thinking about something we don’t talk about enough as leaders: making room. With everything happening right now—winter storms, community unrest, family safety, and the daily realities of school—it’s easy to feel like we have to carry everything ourselves. I’ve been there. Wanting to lead every project. Wanting to be in every decision. Wanting to hold onto responsibi...