Intention, Connection & Relentless Experimentation
tl;dr: Coming out of back to back Evolutionary Leadership Workshops, I thought I’d share the framework of Intention, Connection & Relentless Experimentation. We’re building a community and bringing dreams into the real world.
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I’m experimenting with writing shorter pieces. Let me know what you like better. Your feedback is always welcome.
Before we get started with today’s missive, I want to invite you into a fun thing Tuesday and I are trying out this summer. A friend recently called us her “Naughty Guardian Angels.” And we thought that this would be a perfect name for a lighthearted, playful yet meaningful “advice column.” Encouraged by our community, we want to try it out! We are thinking shorter than 20 minute YouTube videos where we answer questions giving our unique - and we hope fun! - perspectives. . So… all of this to see… Are there any questions you want to ask us?
Now to our regularly scheduled programming…
I am still riding the high of facilitating back-to-back Evolutionary Leadership Workshops: the 2025 cohort of our annual offering, and the second-ever Evolutionary Leadership Graduate Program.
It is a six day workshop designed to make dreams real. It is defined by the framework of:
Intention
Connection
Relentless Experimentation.
Our clear and specific purpose is to take that idea out of your head and into the world. Where it can be seen, touched and experienced. It is for you if you know it is time to make a big change in your life. And you need support through the transition.
This work began ten years ago. When I asked eight friends to join me on a remote island off the coast of British Columbia for the first-ever Evolutionary Leadership Workshop.
It was the beginning of the work that I am proudest of. To this day, the vast majority of participants refer to it as "life changing". They speak of life before the Evolutionary Leadership Workshop and life after. They tell me that they've made some of the best friends of their lives and seeded their most meaningful work collaborations by connecting to this community.
From Workshop to Community
I became a full-time facilitator and consultant back in 2006. I loved my work. But I often felt too constrained by my institutional clients. They wanted to change. But they were not ready to walk to the edges that I knew we had to get to if we really wanted to do something real together.
So I asked a group of friends to join me in an experiment. This was the first time that I was facilitating a workshop that no organization was asking me to design.
Usually an organization calls me in to work with their leadership teams. Or with a broader community of leaders they are convening. Or, in what is now my specialty, they invite me in to design and facilitate fellowships. Deep work. With the same cohort of leaders. Over a period of time. I believe that fellowships are a beautiful way to deepen leadership skills and create the conditions for collaborative emergence.
But that first Evolutionary Leadership Workshop was the first time I was the convener. Not an organization. So I had the freedom to go as deep as I felt necessary for us to reach the transformative edges I was inviting us to explore together.
One of the things I like most about the Evolutionary Leadership Workshop is that it seeds a community. And that while I am the convener of the workshop, I am actually very hands-off after the gathering. The community tends to itself.
A lot has happened in the last ten years. Communities are made up of human beings. There are romances and breakups. There are arguments. There are ideological and personality differences. Misunderstandings. Hurt feelings. Drama. And of course there is me, a terribly fallible convener. It feels like every single one of my screw-ups has reverberations beyond my personal life. This is the hardest part for me.
But here we are. Resilient, learning, growing, forgiving, loving, trying our darndest.
The workshop is about doing real things in the real world: real projects, new businesses, and bold social experiments. It is about doing real things in the context of volatility, uncertainty, complexity and ambiguity. It is about learning how to be when there is no predictable map to what is next.
It was borne out of a passionate belief in evolution. And in what I now understand as a more naive belief in progress. But as I question the linearity of Western narratives, we lean more into the Ways of Wisdom. The way of the ancestors. The narrow path that holds true through the ages.
The Framework
This work is best understood through a simple yet powerful framework: Intention, Connection & Relentless Experimentation. Here is a bit about each:
Intention
We talk a lot about vision. And vision really matters. The Evolutionary Leadership Workshop closes with participants taking their vision stands. And the Graduate Program opens with participants taking their vision stands.
Intention is what animates a vision. It is more deeply connected to desire. To the creative eros that lives within each one of us. I like to remind all people who work with me that the Big Bang is still banging. That we live and breathe in its unfolding. That it is happening right now.
And that as we connect to what we truly want. To our very sense of aliveness. We can actually align ourselves with this Creative Life Force of the Universe. We place ourselves in service. We let ourselves be used.
This is the power of intention.
Connection
This really is the secret sauce of the workshop. It is medicine for the crisis of belonging that defines our time. It is how we enact the belief in co-evolution through friendship. How we integrate the profound understanding that no one has ever made anything alone. That the creative act is profoundly relational. That we find more safety in community, more courage, more healing than in any of the false promises made by capitalist culture.
The way out of abstraction is to come home to our bodies and to learn to trust each other again. Not the adolescent trust that expects people to be perfect. But the self-sovereignty trust that allows us to take risks as we lean into each other. Knowing that each one of us is whole while also tragically imperfect.
We are aiming for the kind of connection that becomes possible when we develop good boundaries. And the capacity for compassion that is directly proportional to the clarity of those boundaries.
We want connection that is deeply interpersonal. But we also want connection that is far beyond the personalities. An emergent and collective interbeing that is greater than any of us imagined.
Relentless Experimentation
We are working with complexity. We are coming to terms with the fact that we are alive in a time that is between paradigms. That there is a dominant but dying paradigm that still has its grip on us. On how we organize ourselves, our livelihoods and our very life force. And that there is a new and emergent paradigm that is still young and has not taken its full form.
We are going to live the fullness of our lives in this space between paradigms.
So we shift our orientation from one where we are looking for experts. To one where we're becoming courageous, skillful, experimenters. We try things. One small experiment at a time. Getting real feedback from the real world. Attuning. Learning. Iterating. And trying again.
We talk about 10-year visions and 3-month plans.
At the end of September, I will hold two back-to-back gatherings where participants from each program will report back on the concrete and tiny experiments that they are running after their workshops. They have about three months to come back with something learned.
Into the Creative Play
These are challenging times, which is why it’s also the perfect time to try new things. And to embrace the humility of knowing less.
Let’s unlock from the grip of a hyper-individualistic, reductionist and materialist modernity.
Let’s release our own attachment to the vestiges of a dying paradigm.
Let’s find out where we are rigid. Learn to breathe, ground and relax. So that we can dance more playfully with this eternal unfolding.
Let’s stay brave, curious, and connected as we keep experimenting together.
PS: My friend and colleague Julian Norris has done it again: The Wisdom Path: Finding Our Way in Liminal Times, Beautifully and concisely captures the intersection between the path of wisdom and working with complexity.