Shoes, Pizza and Vital Leadership

These shoes were made for … spreading joy

There’s nothing like a war to remind you what’s vital. Just ask Rachel Caldwell. She was Director of Pechersk School International (PSI) in Kyiv, Ukraine when the Russian Army invaded Ukraine in February of 2022. It’s not as if the invasion was completely unexpected. Still, nothing quite prepares you for *literal* boots on the ground.

And this is when vital leadership shows up, or doesn’t.

I had the privilege of listening to Rachel’s story as she keynoted the recent ECIS Leadership Conference in Lisbon. I knew I was in for a treat when she sprung onstage wearing red sneakers with pink hearts on them. Yes, appropriate for the conference’s theme: Love-Based Leadership (something in the air about that theme this year!). But also a symbol of how she leads: playfully, grounded in humanity, love-forward. Even when the most serious crisis hits. As if to say: “I’ll go toe-to-toe with your fearsome boots, and I bet my silly shoes will wear you down.”

Here are some key points from Rachel’s story that radiated ‘vitality,’ by which I mean: what is essential, what is energizing, and what is life-sustaining.

-       Her early start in leadership at in international school in Italy coincided with the serious and sustained illness of her young son. Her supervisor assured her that the most important role she could play was being present Mom to her suffering son. He cleared the decks for her, assured her of her job security, and, importantly, took her for pizza every Friday to check in with her and let her know of his ongoing support. This messaging – that she was appreciated, valued, and actively supported – impacted her deeply and influenced her own leadership style, which puts the humans in her care at the vital center.

-       In the months, then weeks leading up to the Russian invasion of Ukraine, she and her team made sure they prioritized what was vital: safe and secure evacuation plans, full support of any staff member choosing to leave Ukraine before such evacuation was necessitated, and laser focus on student (and staff) well-being at all times. The latter continued after evacuation, when the school took up safe harbor with the American School of Warsaw and continued to serve its community in person and online.

-       She is energized by play and joy. Exhibit A: Her shoes. Exhibit B: A video clip she showed of her and the PSI leadership team engaging in a traditional Polish country dance (PSI had been temporarily relocated to Poland by then) as part of a leadership team meeting. They had flowers in their hair and looked as joyful as could be.

-       She understands the importance of sustaining herself, and her team, through restorative practices. According to one of her PSI team members, Rachel incorporated a somatic practice of ‘tapping’ to heal the nervous system during leadership team meetings, especially during the difficult times of the war. She and her family have maintained a home near Turin, which is her sanctuary. She is surrounded by nature there. Her husband Marco, a chef, cares and cooks for her and brings her calm.

Rachel concluded her keynote with a vital question for all of us to ponder: ‘Who will you take out for pizza?’ Which reflects her prioritization of human-centered leadership, her sense of joy, and the importance she places on nurturing self and others.

All elements of vital leadership – in times of war and peace. Spunky shoes optional.

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Inspired by leaders like Rachel, we will explore vital leadership at Sidecar Summit Portugal 2026, at the magical, revitalizing Quinta Carvalhas.

Quinta Carvalhas sits in the hills of Portugal’s Ribatejo Valley, one of the most quietly beautiful places on earth. It’s a place that reinforces what Summits are all about. The light, the bounty of nature, the unhurried rhythm, the nurturing spirit ... there’s a magic here that explains why summiteers return year after year; in this safe, nurturing, beautiful container, deep connections and conversations can flourish.

Alongside me, your facilitators are Lakshmi Karan and Kirsten Pontius, two women who bring depth, experience, and genuine warmth to the question of what vital leadership looks and feels like in practice.

• Dr. Lakshmi Karan co-founded LunARC, a movement putting young people at the center of humanity’s multiplanetary future, bringing to it deep experience across technology, philanthropy, and social innovation. A practitioner of ikigai, she leads with empathy and curiosity.

• Kirsten Pontius is an International Wellbeing Specialist and Certified Health Coach who helps international school leaders move from depletion to vitality. Having lived across 7 countries and partnered with schools from Rwanda to Romania, she brings deep expertise in mindfulness, holistic health and behavioral science. Her framework is simple: sustainable wellbeing is never just a personal project. It is built together, through the communities and cultures we create.

Together, the three of us will facilitate an experience that is intellectually alive, somatically grounded, and distinctly Sidecar: peer-driven, experiential, and designed to send you home with more than you brought.

Sessions will explore:

• What is essential, and what are you carrying that was never yours to carry?

• What does leadership from the future request of you today?

• Where is your leadership energy being generated, and where is it leaking?

• What does aliveness in leadership look and feel like? How do you sustain it, for yourself and your community?

 What you’ll take back with you:

• Peer support and connection that will inspire and last beyond the summit.

• Practical insights, tools and techniques to bring back to your daily life, teams and routines.

• A reset nervous system that has been taken out of ‘fight or flight’ mode, now primed for deep and meaningful reflection and focus, during the Summit and beyond.

• Other takeaways TBD: outcomes depend on inputs!

The Practical Details:

 📅 November 20–24, 2026

📍 Quinta Carvalhas, Portugal

👥 Maximum 16 participants

💬 Three co-facilitators

🏡 Four days/nights full board — accommodations and all meals included

Early bird pricing: $2,195 (Regular pricing: $2,495)

Early bird deadline: May 15, 2026

A deposit of $500 holds your place at the early bird rate. Payment plans are available — reach out to discuss.

Ready to Register? Visit this link.

Extra bonus for showing up with a pair of shoes that can rival Rachel’s.

Yours in prioritizing pizza partners,

Bridget