On The Way To School

If someone had to write a recommendation letter for you, what would it say?

I recently wrote a recommendation for a student, and it got me thinking about how differently we see others than we sometimes see ourselves. We can identify another person's strengths, growth, and defining qualities. But can we do the same for ourselves?

This matters especially when we're pursuing a new opportunity. Being a known quantity can open doors, but eventually, you have to reintroduce yourself and make the case for what you bring.

In this episode of On The Way To School, I explore the value of self-reflection and the importance of articulating your own story—not just what you've accomplished, but who you are and what you contribute.

Here's the exercise: If you were writing a recommendation letter for yourself, what three things would you make sure the reader understood?

Don't wait for someone else to tell your story. Learn how to tell it yourself.

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#OnTheWayToSchool #LeadershipDevelopment #CareerGrowth #SelfReflection #ProfessionalGrowth #EducationalLeadership #Leadership #CareerDevelopment #KnowYourValue #IndependentSchools

A few years ago, I challenged my team to be three things: organized, prepared, and anticipatory. That idea has stayed with me.

Whether we're leading a meeting, teaching a class, or serving a school community, preparation means thinking beyond what we need to accomplish. It means anticipating the people in the room and what will help them engage, contribute, and succeed.

In this episode of On The Way To School, I reflect on what it looks like to bring that intentionality to our work every day—not by giving every ounce of our energy, but by being present and ready to offer our best.

Don't just prepare for the work. Prepare for the people you're serving.

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Distributed leadership matters. Empowering colleagues to lead is essential. But when an organization faces a difficult transition or consequential decision, the person at the top sometimes has to step forward.

Consensus may get you to a decision. It doesn't always determine who needs to communicate it, set the pace, and carry the community through what comes next.

In this episode of On The Way To School, I reflect on leaders' responsibility to recognize those moments and use their authority with clarity and purpose.

Some of the most important leadership doesn't happen at the podium. It happens in the small rooms where difficult decisions are made—and in the conversations that follow.

Don't dilute your leadership when the moment calls for you to lead.

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What does the data say about the health of your school?

I spent some time exploring NAIS’s State of the Independent School Sector dashboard, looking at financial aid, annual giving, and the distribution of teachers and administrators across large coeducational schools on the East and West Coasts.

A few patterns stood out: roughly 43–45% of employees were teachers, 23–25% of students received financial aid, and the average family gift was about $4,600.

But the numbers are only the starting point. They raise bigger questions about administrative capacity, the rising cost of tuition, financial aid, and the role of philanthropy in sustaining a school's program.

In this episode of On The Way To School, I explore why school leaders need to look beyond the headline numbers, understand the context behind the data, and use those insights to inform strategic decisions.

Because good leadership isn't just about having data. It's about knowing what questions to ask of it.

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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.

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#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.

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