"I am convinced that a vision of education rooted in health begins not with information, but with the in/formation of persons committed to the well-being and flourishing of themselves and their communities."

— Dr. Scott Martin

Leading from a Different Place

For too long, we've measured success in education—and leadership—by metrics that don't capture what matters most: the flourishing of human beings.

Almost thirteen years ago, I decided to do something about that, at least in my little corner of the world: education

I launched a school called Odyssey Leadership Academy with the unapologetic pursuit of the North Star of human flourishing

This changes literally EVERYTHING we do regarding the education of human beings in their formative years

At Odyssey Leadership Academy, we dared to ask:

What if we designed everything around human flourishing instead of performance outcomes?

The result was a transformation that produced not just academic success, but persons and leaders who embody wisdom, compassion, and purpose.

This guide shares the five principles that made it possible—and how you can apply them to your own leadership context.

Principle 1: Know Before You Measure

The Problem with Metrics-First Leadership

Most organizations begin with the question: "How do we measure success?"

But when we lead with metrics, we inevitably reduce people to data points—test scores, GPAs, productivity numbers

The Flourishing Alternative

Start with knowing the person, not tracking the performance.

At OLA, every student begins each day in Mentor Time—a sacred space to process celebrations and difficulties.

We don't ask, "What's your GPA?" We ask, "Who are you becoming?"

Mentor Time is our way of making sure every student feels seen, safe, and supported, and that they know in their bones that they belong and that they matter

Application for Your Leadership

Ask yourself:

  • Do I know the stories of the people I lead?

  • Am I creating space for them to be seen as whole persons, not just producers?

  • What would change if I prioritized relational knowing over numerical tracking?

Action Step: Schedule 15-minute "story sessions" with each person you lead. Ask about their journey, their struggles, their dreams. Listen without an agenda to fix or evaluate.

Principle 2: Formation Over Information

The Trap of Content Delivery

We've confused education with information transfer.

We stuff minds with facts, but we don't form hearts.

The result? Knowledgeable people who lack wisdom, virtue, or compassion.

The Flourishing Alternative

Focus on shaping imaginations and affections, not just filling minds.

We don't just teach about justice, compassion, or courage—we create experiences that form these virtues within students.

Students march the Pettus Bridge in Selma. They live among the Cochiti pueblo in New Mexico. They research violence in prisons and present on UNICEF's work defending children. They build tiny homes and plant edible gardens. They lead town halls on adolescent mental health and give spoken words on zip code inequity (you can see the full list of what our students to on our YouTube page HERE).

These experiences don't just inform—they transform them

Application for Your Leadership

Ask yourself:

  • Am I forming people or just filling them with information?

  • What experiences am I creating that shape character, not just competence?

  • How am I modeling the virtues I want to see in others?

Action Step: Design one "formative experience" this quarter—something that will shape the hearts and imaginations of your team toward a shared virtue (e.g., empathy, courage, justice).

Principle 3: Co-Creation Over Compliance

The Cost of Top-Down Control

When leaders dictate every detail, people become passive consumers instead of active creators. They learn to comply, not to innovate. They wait for instructions instead of taking ownership.

The Flourishing Alternative

Invite people into the creative process. Make them architects of their own journey.

At OLA, teachers design their own courses.

Students chart their own inquiry.

Every April, we the faculty ask students what math, science, history, literature, and electives they want to take (and, for our seniors, we ask them what courses they want to teach)

Together, we create curriculum around questions that actually matter:

What is dark matter? How does fatherlessness impact incarceration? What can Tolkien teach us about myth-making?

The result?

Original scholarly work that can't be converted into a grade point average—and students who go to college and into life as thinkers, not test-takers.

Application for Your Leadership

Ask yourself:

  • Am I creating space for others to design and innovate?

  • Do people feel like collaborators or subordinates?

  • What would happen if I invited my team to co-create our vision, curriculum, or strategy?

Action Step: Identify one area where you typically maintain control. This week, invite your team to co-design that process with you. Ask: "What would you create if this were yours to shape?"

Principle 4: Celebration Over Competition

The Anxiety Economy

Grades. Rankings. Performance reviews.

We've built systems that pit people against each other, creating cultures of anxiety, comparison, and burnout.

Research shows that striving for grades creates stress, depression, and self-harm.

Yet we keep doing it because we don't know another way.

The Flourishing Alternative

Celebrate learning. Don't rank it. Foster humanity. Don't track and sort it.

We host quarterly Celebrations of Learning where 200+ community members gather to witness students display their work—art, poetry, spoken word, science experiments, original music, fashion design.

We tell the story of each student's growth. We honor their unique journey.

And we've seen students do ambitious, passionate work without the external pressure of grades.

Application for Your Leadership

Ask yourself:

  • Am I celebrating growth or just evaluating performance?

  • Do people feel they're competing with each other or collaborating toward a shared vision?

  • What would change if I focused on honoring unique contributions instead of ranking them?

Action Step: Create a "celebration ritual" for your team—a regular gathering where you publicly honor learning, growth, and unique contributions (not just results). Make it meaningful and communal.

Principle 5: Rootedness Over Results

The Tyranny of Outcomes

We obsess over outcomes—graduation rates, revenue targets, quarterly goals.

But when we fixate on results, we sacrifice the very things that make results sustainable: rootedness, health, community, and meaning.

The Flourishing Alternative

Cultivate an ecosystem where people are deeply rooted—known, valued, cherished—so they can bear lasting fruit.

At OLA, we work to cultivate rootedness so students can bear the fruit of wisdom, virtue, and compassion.

We create a community of care where every student is cherished for precisely who they are.

We give them the opportunity to tell better stories for their lives and communities.

The outcome? Graduates who receive $2M+ in scholarships, attend top universities, and—more importantly—become leaders who serve from a place of humility and purpose.

Application for Your Leadership

Ask yourself:

  • Am I creating an environment where people feel deeply rooted and secure?

  • Do people know they're valued for who they are, not just what they produce?

  • What would happen if I invested as much in community and belonging as I do in achieving outcomes?

Action Step: Audit your organizational culture. Are you fostering rootedness (safety, belonging, meaning) or just driving toward results? Identify one practice you can implement to deepen people's sense of being known and cherished.

Conclusion: The Invitation

Flourishing-centered leadership isn't easy.

It requires courage to challenge systems built on measurement and control.

It demands patience to invest in formation when everyone's asking for faster results.

But here's what I've learned:

When you lead from a place of human flourishing, the results take care of themselves.

Our students at OLA don't just get into college—they become leaders who change the world.

Our teachers don't just deliver content—they become mentors who shape lives.

Our community doesn't just support a school—they participate in the formation of a better future.

This is the work I now bring to visionary leaders like you.

Whether you lead a school, an organization, or a team, these five principles can transform how you lead—and how the people you lead flourish.

Next Steps: Let's Talk

If you're ready to reimagine what's possible in your leadership context, I'd love to explore how we can work together.

I offer:

  • Leadership Coaching for visionary school leaders and organizational executives

  • Consulting for schools and organizations seeking to reimagine their culture and structure

  • Speaking & Workshops on flourishing-centered leadership, innovative education, and human formation

Contact me:

In Case You Missed It

Did you know that everything I'm sharing in this newsletter series is also drawn out in robust detail in my resource: The Flourishing School Leader's Field Guide?

This field guide unpacks my personal operating system and walks you through creating yours, as well as provides proven strategies to rekindle passion, restore purpose, and create an ecosystem of trust and flourishing in your school community.

It’s essentially everything I cover in my executive coaching sessions in a DIY guide for ONLY $40 bucks!! 

Whether you’re feeling inspired and want to sustain your momentum—or exhausted and in need of renewal—this field guide is your companion for leading with courage, clarity, and care.

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