On The Way To School

This week in my Equity, Justice, and Leadership class, students examined California ballot propositions, considered competing perspectives, and made recommendations grounded in equity, justice, and leadership.
I was struck by how seriously they took their responsibility to educate one another.
Civic engagement starts long before the first ballot. It begins with asking questions, evaluating information, challenging assumptions, and understanding how decisions affect others.
That experience got me thinking about our responsibility as educators: Are we simply teaching students about leadership, or are we giving them opportunities to practice it?
In this episode of On The Way To School, I reflect on why student voice matters and why we should create space for young people to engage with the issues shaping their communities.
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#OnTheWayToSchool #CivicEngagement #CivicEducation #EducationalLeadership #StudentVoice #YouthLeadership #EquityJusticeAndLeadership #IndependentSchools #CriticalThinking #Education

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 of fuel on the inside.
You’re pouring into everyone else’s cup. You’re motivating your team. You’re showing up for your students, your colleagues, your family, and your community.
But what happens when the things that once brought you joy start feeling like obligations? When your patience gets shorter? When you’re still producing, still achieving, still winning—but you’re no longer feeling restored?
Your productivity is not your worth.
As leaders, we can become so accustomed to being the resource for everyone else that we forget we are people, too. Our value cannot rest solely on what we accomplish or how much we give away.
Rest is not a reward you earn after you’ve done enough. It’s part of what allows you to keep showing up as your fullest self.
So as we approach the upcoming breaks and the final stretch of the year, I want you to ask yourself two questions:
Am I winning?
And just as importantly, am I well?
Find your source of restoration. Reconnect with what grounds you. Make space for the things that replenish you—not because someone else needs you to be at your best, but because you deserve to be well.
You can’t pour endlessly without replenishing what’s within you.
🎧 Listen to today’s episode of On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #EducationalLeadership #SchoolLeadership #LeadershipWellness #RestAndRestoration #BurnoutPrevention #SelfCare #LeadershipDevelopment #EducatorWellness #SchoolCulture #LeadWithPurpose

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 for a new connection?
In my Equity, Justice, and Leadership class, I’ve been intentional about pairing students with classmates they might not ordinarily work with. What I’ve noticed is that when students have the opportunity to work together more than once, something shifts. Comfort grows. Conversations deepen. And new learning becomes possible.
The same is true for us as educators and leaders.
We can work alongside someone for years without ever really collaborating with them. We can sit in the same meetings, share the same hallways, and still know very little about how that person thinks, what they bring to the table, or what we might accomplish together.
So here’s your challenge: Change your seat. Find a new collaborator. Start a conversation with someone outside your usual circle.
You don’t need a professional development day to do it. Sometimes, the opportunity you’ve been looking for begins with a simple decision to work with someone different.
You might discover a new perspective, a stronger partnership, or even a renewed spark in your own work.
We’re back for Season 10, and I’m looking forward to learning alongside you.
🎧 Listen to On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #Season10 #EducationalLeadership #SchoolLeadership #SchoolCulture #ProfessionalLearning #Collaboration #EquityAndJustice #IndependentSchools #LeadershipDevelopment #EducatorLife

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 about opportunity.
And often, we make those decisions because we believe we know what will give our children the best possible future.
But what happens when the choice we made for them becomes something they have to live with?
That question works in both directions.
Sometimes we choose the school because we believe it is the “best” school—even when our child may not thrive there.
Sometimes we reject a school because it doesn’t carry the prestige we think our child needs—even when that school might be exactly where they could flourish.
And sometimes, as Hannah-Jones’s story illustrates, we make a choice rooted in values that are deeply meaningful to us, only to discover that our child is experiencing the consequences differently than we imagined.
Our children have to live the education we choose for them.
So maybe part of our responsibility as parents and educators is to disrupt our own definition of what “good” looks like.
There are more than 50 colleges worth considering. There are extraordinary schools that don’t carry the biggest brand names. There are many paths to meaningful work, leadership, creativity, and success.
The question isn’t simply, “Is this a good school?”
It’s “Is this good for my child?”
And perhaps most importantly: When we learn that it isn’t, are we willing to change course?
🎧 Listen to today’s episode of On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #EducationalLeadership #Parenting #CollegeAdmissions #CollegeAccess #IndependentSchools #SchoolLeadership #StudentSuccess #EducationLeadership #ParentPartnership #K12Education #LonelyGraduation

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 thing about recognition: it may have your name on it, but it rarely belongs to you alone.
I was also able to return to the football field, participate in the homecoming coin toss, and share the experience with my son. After more than 20 years, watching a game at the place where I once played felt like one of those full-circle moments you don’t plan for.
And now, I get to carry that gratitude forward.
Tonight, I’ll be back at Lore Leimert Park with Yetunde Daniels Rubinstein and Timothy Fields for a conversation about the continuum of care—the conversations families need to have as students move through K–12, toward college, and into the very different world that begins once they arrive on campus.
Not a panel of experts telling families what to do.
A conversation about the real challenges families face—and how we can work through them together.
Because maybe that’s what this season of life is really about: remembering who helped us along the way, and becoming that person for someone else.
🎧 Listen to today’s episode of On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #EducationalLeadership #SchoolLeadership #IndependentSchools #CollegeAccess #CollegeAdmissions #ParentPartnership #StudentSuccess #EducationLeadership #Leadership #LonelyGraduation #Community

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 protect their institutional mission.
My advice?
Have a plan.
Before putting anything into motion, understand what you’re trying to accomplish, build your approach, and—most importantly—talk to your counsel. Legal counsel is there to help schools navigate moments like this thoughtfully and responsibly.
But there’s another piece of this conversation that I think we can’t overlook:
Research.
Independent schools need more peer-reviewed scholarship that documents what practitioners, administrators, faculty, and boards are actually experiencing.
We need to document this moment.
We need to capture the decisions being made, the challenges schools are facing, and the lessons we’re learning along the way.
Because when the voice of practitioners—and the scholarship that captures their experiences—is missing, we lose context. We lose history. And we risk repeating the same challenges in the future.
My own doctoral research began with that same idea: when there’s a gap in the literature, sometimes the responsibility is to help fill it.
So as independent schools navigate this moment, let’s not just react to what’s happening.
Let’s document it. Study it. Learn from it. And help shape what comes next.
🎧 Listen to today’s episode of On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #SchoolLeadership #EducationalLeadership #SchoolGovernance #IndependentSchools #SchoolBoards #EducationLeadership #EducationalResearch #SchoolGovernance #IndependentSchoolLeadership #NonprofitLeadership #SchoolCulture

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. Practical tips for engaging at school events and connecting with new people round out the episode.

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, try something new, navigate a difficult social moment, or simply sit with the discomfort of not knowing what comes next.
That can be especially hard when students leave home for college.
Suddenly, the scaffolds are different. The social structures are different. And they have to begin developing the skills to create community for themselves.
That doesn't mean we stop listening.
It doesn't mean we ignore real struggle.
It means we learn to distinguish between supporting a student and solving the problem for them.
Because sometimes there really is nothing we can do.
They need the experience.
They need the reps.
And you don't get the reps without giving students enough room to take some healthy risks, make mistakes, and discover that they can handle more than they thought.
🎧 Listen to today’s episode of On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #SchoolLeadership #Parenting #StudentDevelopment #Resilience #CollegeTransition #EducationalLeadership #StudentBelonging #Independence #SchoolCulture #Education

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 — and warns about the secondary impact on charitable deductibility and fundraising.

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.
Don’t wait two weeks for the formal check-in. Walk by. Say hello. Ask how the day is going. Give them a place to process the small things that can feel enormous when you’re brand new.
And remind them: you don’t have to be perfect on day one.
You’re building reps.
For school leaders, sometimes the most meaningful support isn’t another meeting, another document, or another evaluation.
Sometimes, it’s simply being present.
Give your new faculty some love. They’re not just learning how to teach at your school.
They’re learning how to belong there.
🎧 Listen to today’s episode of On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #SchoolLeadership #EducationalLeadership #NewFaculty #TeacherSupport #FacultyCulture #IndependentSchools #SchoolCulture #TeacherRetention #EducationLeadership
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