“no hay camino,
se hace camino al andar...
there is no path,
The path is made by walking...”
Encuentro Wingspan
Join us for an international space curated for leaders like you who are leading for exceptional social good.
password: muchtodare
You could use some Mediterranean in your leadership...
But here’s the thing… this is not about a gorgeous backdrop.
It’s about your leadership — and learning from others who are leading for good.
Leaders who are healthy and well lead organizations that are healthy and well.
Take time to connect with a collection of selected bad-ass leaders like you who are invested in the collective agency of other leaders – leaders who give deeply and are ready to be restored in return.
Welcome to Encuentro Wingspan
Encuentro — Spanish for “encounter” — a space to reconnect with yourself, others, and your leadership.
Six days. Five nights. An international gathering near the Costa Blanca on the Mediterranean Sea in Alicante, Spain.
A tech-free space — with no constant demands, no performance, and no pressure to have it all figured out.
Just you—and a carefully selected group of leaders leading for exceptional social good—coming together to do the worthy work of reconnecting with yourself, each other, and the way you want to lead.
Because you’re not wilting.
You’re just overdue for sun and sea — and the nourishing soil of community.
Here’s what you can expect:
Here’s What You Can Expect:
A Shared Villa Experience in Spain - Staying together in a private home with your room (or a shared room for two with more accessible rate) —designed for both connection and solitude. Space to gather, space to retreat, space to breathe.
Facilitated Leadership Conversations - Thoughtfully guided group conversations that move beyond surface-level sharing into the kinds of reflections leaders rarely have time or space for.
1:1 Leadership Coaching - Individual coaching with JoJo Longbottom or Ryan Maxwell, drawing on decades of experience leading and supporting leaders in social good, education, and mission-driven work.
Guided Reflections & Journal Prompts - Invitations to unpack what you’ve been carrying—personally and professionally—and to reconnect with the clarity that first called you into leadership.
Walk-and-Talks & Time for Connection - Unstructured and lightly facilitated time with other exceptional leaders—conversations that unfold naturally and matter deeply.
Rest & Solo Space - Because a siesta isn’t lazy …it’s essential. Time built into the rhythm for naps, reflection, oceanside reflection, time to float in the pool, or quiet solo walks. Drawing on the ideas of Outward Bound, time for reflection to make sense of what the space and people offer you to learn.
Fellow Leader-led Talks - Coffee Talk in the Morning, Evening “Vesper” — these conversations are brought and led by you and your fellow leaders.
Evenings of Connection - Shared meals, laughter, and the kind of storytelling that only happens when people are connected enough to be real.
Good Food. Good Company. Real Talk.
- Meals are handled. The setting is curated.
Your only job is to show up (at our meet up spot at the airport or train station) present—and maybe a little jetlagged & hungry.
All meals & drinks included.
All accommodations included.
All transport from our rendezvous to the villa and back again included.
Travel far away to find yourself waiting there.
This isn’t a “retreat” in the soft sense.
It’s an encounter.
A chance to find yourself again and reset your direction, what matters.
A chance to set down the noise and reconnect with the leader—and human—you’re becoming.
There will be space to unplug, but not escape.
Time to slow down, without checking out.
Room to be honest, without performing.
Just you, your reflections, and a small group of exceptional leaders—people of character who are ready to listen deeply, speak truthfully, and walk alongside one another in the work that matters.
This is leadership done the human way.
your facilitators:
JoJo Longbottom & Ryan Maxwell
JoJo Longbottom:
Joseph (JoJo) Longbottom is a systems-level education leader, researcher, and facilitator focused on organizational learning, leadership development, and systems transformation. He holds a Doctor of Education (Ed.D.) in Education Leadership from the Harvard Graduate School of Education, where he completed the highly selective Education Leadership (Ed.L.D.) program.
JoJo’s professional experience spans classroom teaching, school leadership, district-level work, research, and national education initiatives. He has served as a principal, instructional coach, researcher, and consultant, supporting schools and organizations in strengthening decision-making, collaboration, and improvement practices.
JoJo works at the intersection of research and practice, helping organizations use evidence, improvement science, and collaborative inquiry to address complex challenges. His work emphasizes collective problem-solving, learning across differences, and building systems that support continuous improvement.
JoJo brings his sense of humor — alongside a calm, analytical, and relational facilitation style — to leadership spaces. He is particularly skilled at helping leaders surface assumptions, examine patterns, and engage in thoughtful dialogue that leads to clearer thinking and more coherent action.
Ryan Maxwell:
Ryan’s spent decades leading in education, social justice, and non-profits. From teaching in Oakland to founding schools in Chicago to national leadership roles, he’s been there — wherever you are in your leadership journey — and he’s got the scars and stories of failure and falling down to prove it. Fluent in (South American) Spanish, he’s also a former camp counselor, which means you’ll get leadership coaching mixed with campfire storytelling and possibly a sing-a-long if you ask more than once. A leadership coach and strategic planning advisor to non-profits and do-gooders, Ryan hosts the "Exceptionally Good Podcast," where he dives deep with world-changers about the complexity of what leadership really means.
Listo? Lista? Are You Ready to Show Up?
Not just for this retreat—for your life, your work, and the people you serve.
The world doesn’t need more leaders pretending they’ve got it all together. It needs leaders who are brave enough to slow down, be honest, and do the work that matters.
With a belly full of paella.
Join us. Get real. Create space. And return ready to lead in a way that has been just out of reach.
the details:
Dates: June 13 – June 18, 2026 (Saturday through Thursday)
Location: Spain — near a small down on the Costa Blanca, near Alicante — rendezvous location announced soon
Lodging: A private villa in near the coast of the Mediterranean — your own room or two-to-a-room for a more accessible price (your choice).
Meals: All-inclusive (we’ll feed you & you feed your soul)
Transport: from rendezvous spot and back all included.
Agenda: Leadership coaching, reflection, group work, exploration time, real talk
Your team, your family, and the world need the best version of you.
Vamos.
Limited Sliding Scale:
Pay-it-Forward rate helps others … and "Accessible” rate supports those who need it.
In order to cover costs, there are limited sliding scale and shared room spots available.
Cost includes everything from pick up spot to drop off: all local transport, food, lodging, and light facilitation by JoJo & Ryan.
Cost does not include airfare.
See registration for cost options.
Single Room Rates
Single Rooms available — with a sliding scale.
Shared Room Rates
Share a room with one other person.
(We will pair two leaders who request to room with one another. Otherwise, we will make a suitable match for you.)
Limited spots.
Spots are limited.
8-12 leaders.
When it is full, it is full.
Your team—and the world—need the best version of you.
Carrying it all alone isn’t strength; it’s unsustainable.
You don’t help anyone by doing that.
And you don’t have to.
We’ve got you.
Spread your wings. Vamos.