EdgeworkLife™

Blog, articles, stories, and thinking out loud

Serene mountain landscape at sunrise with multiple mountain ridges and mist in valleys.

“Your experience can profoundly affect the people around you whether you are aware of it or not.”

- Brené Brown

Our stories matter.

In our personal life and professsional role, showing up authentically as ourselves, succeeding and failing greatly, being brave, and forging our own path is what it’s all about.

Sharing our journeys through stories and writings allows us to process these experiences, understand what we have learned, and recognize where the journey has brought us.

Sharing our stories and ideas requires courage and vulnerability, and through these processes we revisit many of the same emotions we experienced on the journey itself -self-doubt, shame, confusion, exhilaration, humility. In the sharing of our stories, we help others along their journey as well.

That’s the intention of this Blog: EgeworkLife. Here you will find stories of lessons learned, grand adventures, van life, everyday life, and life and work “on the edge.”

Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

What Keeps You Awake at Night?

Boards often wonder what their head of school is thinking. “What keeps you awake at night?” is a question I hear boards asking their heads. At the center of that question is genuine curiosity and, with well-functioning boards, a genuine desire to be helpful.

How that question lands, and how the head responds, depends greatly on the health of the board-head relationship.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Managing Uncertainty: Touchstones

We all experience moments and periods of uncertainty - in our work and in our lives.

But if we can sit in uncertainty long enough and embrace our feelings of instability, we are often rewarded with new creative insights and a renewed sense of direction.

The key to sitting in our discomfort is to have touchstones that calm our nervous systems. Touchstones can be rituals, objects, routines, and even other people.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Over the Edge: Celebrating One Year of Adventure

Exactly one year ago, five days after retiring from a 20-year headship and 40 years of leading schools, I arrived in Australia.

I stepped boldly over the edge — launched a coaching and consulting business, moved into vanlife with my partner, learned to swim, and built a Seattle + Australia life from scratch.

A year in, I wrote down what this experience has taught (and re-taught) me about EdgeworkLife, the framework I've built my work around for decades.

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Belonging Kirk Wheeler, Ed.D. Belonging Kirk Wheeler, Ed.D.

Designing for Belonging

Back in Seattle for now, I was reflecting on the sense of place, of home, I experience when I’m in Australia and in Brandy. Crazy that a van can evoke that sense of belonging. What makes it feel so good? Why does it feel homey? I believe the answer lies, at least partially, in good design.

I am a total architecture and design geek. I absolutely love designing schools. I believe the physical environment matters more than we realize. Simply put - our physical environment impacts how we feel, work, and learn.

There are six elements of intentional design that support a sense of belonging and connection - whether in our schools, at home, or even in a van.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Getting Comfortable with Discomfort

Our tendency is to seek comfort even when it's counter to our well-being and growth. By leaning into edgework - uncovering our fears, reflecting on where we are, getting clarity on what we want, and understanding our strengths - we can embrace personal and professional growth and take the next step. Ultimately, we thrive when we have a deeper awareness of what’s keeping us our comfort zone. And, therefore, keeping us from growing.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Rebuilding Ourselves

I am rebuilding the cantilevered decks at my condo in Seattle. Like most significant changes, this has required careful planning and prep, the destruction of what was, and a commitment to a new version that's even stronger than before.

The rebuild of our careers (whether we’ve chosen to make a change or the change comes unbidden) also involves some degree of planning and preparation. Significant change also involves the creative destruction of what was.

And then we rebuild. And we are stronger than before.

As I coach the team at St. E’s, I ground myself in five core beliefs. Dive in!

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

The Power of Why

I was recently working with a client who was wrestling with a familiar question: should she stay in education — continue doing work she loves and is good at – or follow a passion and try something new?

It's a question I hear often. And what I notice, almost every time, is that the energy is entirely focused on the what. What should I do next? What are my options? What makes the most sense?

The what is important. But it isn't where I start.

I start with why.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Taking Chances

"Life is too short not to take chances on yourself.”


Lindsey Vonn didn't just mean athletic risk. She meant the deeper kind of risk taking— the decision to bet on your own potential and capacity even when the path forward is uncertain and the outcome isn't guaranteed.

I’ve been pondering this lately in my own journey and in my work with others. When you have goal or a dream, or are just ready to take a chance on yourself, here is my advice.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

On Longing and Belonging

7,350 miles from Seattle. As someone who coaches leaders through transitions, I'm living one of the core challenges I work with: how to build belonging in a new place without losing connection to the communities that shaped you?

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Stories with Brandy: Grace and Gratitude

Stories with Brandy - a storytelling evening at our Australian home, our camper van named Brandy. Our theme, Gratitude and Grace, framed stories about the unexpected and becoming grateful for what we don’t get. This is my story.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Living in the Liminal: Why Threshold Spaces Are Essential to Edgeworklife

We pack for our insecurities when facing life's transitions, but what we're really preparing for is liminality – those uncomfortable, transformative spaces between who we were and who we're becoming. Instead of packing for control, we need to cultivate curiosity over certainty, flexibility over fixed plans, and trust over total control. Guided by joy, flexibility, and generosity, these threshold spaces teach us to live the questions rather than rush to answers.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Packing for Our Insecurities

"We pack for our insecurities," my friend told me. And he's right – both literally and metaphorically.

As I prepare for this bi-coastal, van life adventure with Jared, I'm discovering that packing isn't just about socks and chargers (though I definitely overthought both). It's about the emotional baggage we carry when we leap into the unknown.

Eight pairs of socks, two dress shirts, endless tech chargers – each item represents a "what if" my brain has conjured up. But here's the edgeworklife insight: we need enough preparation to feel brave, not so much that we're paralyzed by every possible scenario.

The van is waiting. The adventure is calling. And sometimes the most important thing we pack is trust that we'll figure it out as we go.

What are you packing for your next leap?

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Jump!

After 40+ years in education and 20 years as a head of school, I'm standing on the edge of my biggest adventure yet. Retirement? Not quite. I'm calling it my gap year — launching my coaching and consulting practice while building a bi-coastal life between Seattle and Australia's Sunshine Coast with my partner Jared.

Edgework is about intentionally moving to the edge of our experience, knowledge, and confidence — because that's where all learning happens. Now I'm taking my own leap, guided by three touchstones: Joy, Flexibility, and Generosity.

From international school leadership to #vanlife adventures, from classroom teaching to life coaching — this is what edgeworklife looks like. The jump is scary, but the adventure is just beginning.

Ready to explore your own edge?

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

3 Ways Parents Can Build Character: How parents and teachers can work together

When we send our kids to school, we want to trust that the teachers and staff will aid in our child’s well-rounded development. Unlike test scores and grades, it can be hard for parents to evaluate how a school’s community, environment and curriculum support a student’s character growth.  

Here are three tips to consider this school year to nurture character development at home and in the classroom.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

11 things I Want Parents to Know

As a former head of school and an educator for over 40 years, and a parent myself, I've partnered with many parents, coached dozens of teachers, developed hundreds of school policies, mentored other school leaders and worked through countless challenging moments. I've learned a lot along the way! As we head into the summer, here are 11 things I want parents to know.

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Farewell - and hello!

Saying farewell to 20 years as head of school and 40 years in education and HELLO to new adventures!

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Kirk Wheeler, Ed.D. Kirk Wheeler, Ed.D.

Running to Belong

We are all in the process of growing and evolving. We all have our edgework. Read Weiwen’s story of finding a community and sense of belonging through running.

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