Leadership, Philosophy & Healing Politics: Courage, Burnout & Becoming Your Best Self

An interview with Skippy Mesirow

Skippy Mesirow is a leadership coach, former Aspen City Councilmember, and founder of The CIVIC COURAGE LAB—a multidisciplinary training ground helping public servants and civic visionaries rise into their highest potential: their Arête. He’s the creator and host of Healing Our Politics, a global top 10% podcast featuring guests like Byron Katie, Dr. Gabor Maté, and Jerry Colonna. He also leads SANCTUM, a fully licensed Natural Medicine Healing Center in Aspen, CO. His work fuses deep inner work, relational mastery, and peak performance—guided by classical philosophical schools of thought to help leaders thrive mentally, emotionally, and politically.

Skippy Mesirow is an esteemed guest speaker at our upcoming virtual event Tyranny and Democracy Saturday July 26 at 1 pm EDT. This is a free event open to all. Donations welcome.

How did you first become interested in Philosophy and politics?

I grew up in a home shaped by contradiction—living with my grandparents during a nearly decade-long divorce. My grandmother said I’d be interested in politics. I thought she was crazy. All I wanted was to escape. And I did—through the unlikely alchemy of trauma, privilege, and curiosity. I traveled the world on motorcycles and with a backpack, seeking out belief systems and ways of living as different from mine as possible. I wasn’t obsessed with politics or philosophy, at least not in name—I was obsessed with understanding what makes us human. Over time, I realized politics was where we could shape change at scale. But it wasn’t until I burned out in public office that I saw the full picture: the architecture of the mind and the structure of society are inseparable. You can’t change the world without also changing the one trying to do the changing.

Tell us about the Healing Our Politics Podcast.

Healing Our Politics is a live, intimate conversation series with thinkers, healers, and public leaders who are redefining what it means to lead well by living well. We explore the Six Pillars of Empowered Leadership—mental, physical, emotional, social, financial, and spiritual well-being—and speak candidly about burnout, belonging, identity, and integrity. The goal? Help public servants thrive as full humans, not just titles. Join us for conversations with renowned voices like Byron Katie, Gabor Maté, David Allen, Jerry Colonna, and Rick Doblin, as well as lesser-known but deeply impactful leaders like Kurt Gray, Shakeyla Ingram, and Eldra Jackson III.

Do you have a favorite quote that you use?

A ship is safe in harbor, but that is not what ships are built for.

John A. Shedd

This quote has lived in my bones for years. It reminds me that safety isn’t the goal—service is. We weren’t built for comfort, but for courage. And courage, by definition, demands two elements: fear and love.

Our work is not to rid ourselves of fear, suppress emotion, or escape discomfort. It’s to embrace it all—to sail through the storm with presence, skill, and vision. True mastery isn’t about avoiding the waves—it’s learning how to ride them while bringing and nurturing others with you toward something better.

In this way of being our roadblocks become our building blocks.

As I often say: The challenge IS the way.

As the cofounder of the Elected Leaders Collective, you mentioned turning 'crisis into creation' and 'roadblocks into building blocks'—can you share how your personal journey of healing and transformation has most directly shaped the way you design support for other leaders in your organization?

My second year on City Council should’ve broken me—COVID, social isolation, the edge of financial ruin, and life and death public decision-making. But it became the most transformative year of my life. Decades of inner work suddenly crystallized into answers—about my anxiety, my failed relationships, and my role in the very toxicity I sought to change.

That experience led me to found the Elected Leaders Collective, first serving fellow electeds. Within a year, we were supporting a wide swath of those seeking to create a better world, government, nonprofit, entrepreneurs, educators, and first responders —people united by a shared calling to serve with greater wholeness and less burnout. We have become the training place for the inner journey of public leadership.

Today, that work has evolved into The CIVIC COURAGE LAB, home of the COURAGE METHOD™, a transformational framework that weaves together somatic tools, philosophical inquiry, and performance training to help leaders thrive. We will formally rebrand and re-launch prior to the summit. For now, visit us at…

📍 www.electedleaderscollective.com

Suppose you were able to give a talk or workshop at the original location of Plato’s Academy, in Athens.

I would feel nervous. Honored. Humbled. And ready. Part of me would ask, “Who am I to speak here?” And another part would remember: I’m human—just like Plato, just like all those who came before.

As the Rabbi in Pirkei Avot teaches

It is not your responsibility to finish the work, but neither may you desist from it.

I would gather the best of what I’ve learned, align deeply with the moment, and offer the most courageous teaching I could: guiding leaders to embody their Personal Arête Protocol—a which delivers spiritual compound interest for each user towards their unique zone of service genius. One small step toward manifesting the north star Aristotle pointed us to, millennia ago.

What question would you like to leave us to think about?

This could be a question you’re still pondering yourself or just one that you’d like our readers to consider and try to answer. It should relate to the answers you gave above, if possible. You may wish to comment briefly on why it’s an important question but leave it unanswered as we’d like our audience to engage with it online by posting their comments and responses.

What if the most world-changing thing you could do… was to become more fully yourself?

Ask not: “Who should I become to succeed?” but: “Who was I before the world told me who to be?”

The most powerful leaders don’t chase identity. They embody integrity.

Tell us, who were you meant to be—without limitation?