On The Way To School

S10 E161 Dr. Chris Dennis reflects on the Pollyanna Conference going virtual, the difference between announcements and invitations, and the importance of intentional connection, belonging, and asking yourself "What do you want?" in leadership and life.

S10 E160 In today’s episode of On The Way To School, Dr. Chris Dennis reflects on the idea of capacity, our individual ability to perform, endure, and create at high levels. As January unfolds with its demands and momentum, this episode invites educators and leaders to pause and ask: Am I operating at my full capacity, and do I recognize what that really is? Dr. Dennis explores how capacity looks...

📍S10 E159: We’re 15 days into 2026, so I had to pause and check in with myself and with you. Are you still motivated? Or has the energy started to fade already? In today’s episode, I talk about the difference between motivation and belief. Motivation comes and goes. Belief is what carries you when the excitement wears off. You can believe and feel unsure. You can believe and be scared. But belief...

Host Dr. Chris Dennis checks in with administrators and educators about helping students return after winter break, offering classroom reflections and practical tips for regulation and community building. He reflects on recent events—including the January 6th discussion in class, the Palisades/Eaton fires anniversary, and a Minneapolis tragedy involving ICE—encouraging leaders to help young people...

S10 E157 Dr. Chris Dennis reviews seven practical tips from Responsive Classroom to help students transition back after winter break: plan something to look forward to, set personal and academic goals, provide socialization time, ease into academics, review routines and expectations, extend patience and empathy, and revisit favorite activities. The episode highlights being mindful of students who...

S10 E156 In this episode, Dr. Chris Dennis shares three practical strategies for school leaders returning from winter break: be mindful and relatable, be present (and bring snacks), and clearly communicate what's coming next. These approaches help rebuild collegial connections and set clear expectations for the busy weeks ahead. Whether you're an administrator or teacher, you can implement these t...

Welcome to my New Year episode of On the Way to School, a short, warm check-in for educators and administrators as we prepare to return after winter break. I reflect on the importance of rest and share some family moments, including the joy of becoming a new grandparent. I also delve into the emotional realities of the season and offer practical steps for getting back into the school routine. Some...

Dr. Chris Dennis shares a personal year-end reflection on family rituals, a vision-casting family meeting from 2020, and how written goals have guided progress toward five- and twenty-year plans. He encourages listeners to create their own traditions and milestones, mentions plans for winter break and a grandson's visit, and thanks the audience as the podcast approaches a seasonal pause.

Dr. Chris Dennis discusses how educators can solve problems more effectively by using strategic "angles of pursuit" instead of trailing issues reactively. Through analogies with an off-leash dog, a sheepdog, and football pursuit drills, he shows how a coordinated, proactive team approach funnels problems into solvable paths. The episode urges leaders to position themselves over the top, take wider...

Dr. Chris Dennis offers a short, six-minute episode for educators feeling exhausted as the semester intensifies. He shares a simple practice: scrolling through summer photos to reconnect with joyful memories and restore energy. The episode encourages keeping meaningful moments close, considering analog prints or slideshows, and planning small restorative experiences before winter break to replenis...

In this episode, Dr. Chris Dennis sits down with Mr. Javon’e, an energetic K–6 classroom teacher and STEAM specialist whose authentic presence transforms his students’ days. They discuss classroom moments like erupting volcano labs, the balance between structure and excitement, and what administrators should understand about teachers’ day‑to‑day realities. Mr. Javon’e shares his personal journey f...

Dr. Chris Dennis talks with Jenn Wells, EdD , UCLA’s chief of staff for alumni engagement, about the evolving chief-of-staff role in higher education, systems-focused equity work, and how to build buy-in for strategic change across institutions. Jenn shares practical advice for equity practitioners on transferable skills, avoiding burnout, and career pivots, and closes by describing her own outlet...

We’re back with the second half of my conversation with my brother, friend, and the creator of the On The Way To School theme music, Adrian Perryman. In this episode, we dive deeper into identity, creativity, and the freedom to pursue joy outside of our job titles. Adrian opens up about being a Black nerd in cosplay and Comic-Con culture, navigating representation, and finding community in spaces...

Dr. Chris Dennis interviews Adrian Perryman, the producer behind the podcast’s music and director of the GHR Fellows Program at the University of St. Thomas. They discuss the story behind the show’s instrumental, Adrian’s role in higher education, and his commitment to connecting students with community opportunities. Adrian also shares how creativity fuels him,  from 3D printing and cosplay to mu...

Dr. Dennis reflects on the importance of the "spark", that inner motivation that drives leaders, energizes teams, and guides hiring decisions. He encourages listeners to reignite their passion, seek candidates with enthusiasm and growth mindsets, and surround themselves with people who uplift and challenge them. Through personal reflection and practical prompts, this short episode asks when you la...

Dr. Chris Dennis returns after Thanksgiving to discuss the "calibration week" teachers face, planning for the months ahead, and using a 12-week year mindset to make goals more achievable. He shares personal reflections from family goal-setting, previews his upcoming book Lonely Graduation, and teases guest hosts coming soon to the podcast.

This episode examines a form of discipline that prepares rather than punishes, utilizing athletic experience to demonstrate why consistency and readiness are essential to effective leadership. Dr. Chris Dennis outlines three core ideas: discipline is about respect (not control), consistency stabilizes teams and enables risk-taking, and discipline strengthens your identity, allowing you to handle u...

Greetings and welcome back to On the Way to School, the podcast for educators and administrators ready to start their day with a boost. I’m Dr. Chris Dennis. In this episode, we delve into board culture, examine why silence can be more detrimental than disagreement, and discuss how unhealthy boards can harm schools. Dr. Dennis shares a framework for culturally affirming governance focused on honor...

Dr. Chris Dennis explores how school leaders can lead with principle instead of neutrality during politically charged times, from government shutdowns to culture wars and book bans. He outlines practical steps, states clear values publicly, backs faculty, invites disagreement but bans disrespect, protects marginalized students, and anchors decisions in mission to help leaders navigate crises and s...

In this episode of On the Way to School, Dr. Chris Dennis delves into one of the biggest challenges for educators and leaders today: effective time management. He shares real talk about what happens when busyness takes over purpose and how to reclaim your calendar without losing your impact. With practical tips on setting boundaries, protecting your energy, and delegating with confidence, Dr. Denn...

In this episode of On The Way to School, Dr. Chris Dennis reflects on what it means to lead when the room is tired. After a long night of delayed flights returning from Nashville, and still waiting for his grandson, Bishop, to arrive, he shares insights about showing up with authenticity and care, even when energy is low. Dr. Dennis explores three key principles: acknowledging others’ effort, find...

Dr. Chris Dennis explains the importance of timely pulse surveys and an equity & inclusion tool to gather reliable feedback from faculty, staff, and families before holiday breaks. He emphasizes using data responsibly, bringing in institutional research to avoid bias, protecting anonymity while engaging respondents, and turning survey results into clear, evidence-based actions.

In this episode, Dr. Chris Dennis explains how educators can share difficult news with parents while preserving trust, dignity, and equity. He outlines three pillars: honoring the family’s experience, ensuring fairness, and respecting cultural context—and emphasizes clear structure, affirmation, and a sustainable path forward. Listeners will receive practical steps and sample language for deliveri...

Host Dr. Chris Dennis explores the mid-year pressures school leaders face — grading periods, conferences, and the tough decisions that shape classroom and school outcomes. He explains how data, feedback, preparation, and empathy guide course corrections, and reminds listeners that hard choices grounded in values aim to improve experiences for students, staff, and families.

Host Dr. Chris Dennis recaps a busy week: chaperoning sixth graders to Catalina Island, attending the Harvard-Westlake Pollyanna Conference on neurodiversity, and an energizing board meeting highlighting the advanced inquiry curriculum. He reflects on building relationships with students and staff, the importance of supporting neurodivergent community members, and reminds educators to prioritize s...