Essential Insights from the Messy Middle
- Michelle Holliday
- May 25
- 7 min read
Updated: May 28

"Being in and with the messy middle" turned out to be a richly evocative theme within our OD for Life European gathering earlier this month. As I've taken the past weeks to untangle insights from our days together, I find that the metaphor may hold everything we need. I'll share below what is alive in me, adding to wonderful reflections from others.
The theme came from a thoughtful process of discernment among stewards of this community of Organizational Development practitioners. And it held within it several related questions:
How do we acknowledge the complexity of our times?
What do our own patterns and emotions reveal about the world’s deeper currents?
How do we grow the capacities that are being called for now?
At times during our three days together, "the messy middle" pointed to a time of uncertain transition, as if it were a point along a path.
In particular, we noted that the field of Organizational Development is in a moment of evolution and vulnerability. In this shift, we saw the risk of carrying forward old ways, or of the movement being co-opted in some ways.
Our sense was that these annual OD for Life gatherings add some momentum to the field's evolution. "To be in the middle of that is a great place to be," one of us shared. The actual place where we gathered, Wir bauen Zukunft, added enormously to our experience. "See, hear, smell the future here," one steward of the place said. "Lie on the ground of the future here."
In reflecting on the assumptions that guide us in practicing "organizational development for life," we felt the rawness of our longing for deeper alignment with life. Someone offered a quote about being "homesick for a future state that is not here yet." Another observed: "This 'in between' is taking all of my patience. I just want it to be over. At the same time, it’s an honor to be alive now. What matters is to be aware."
The "middle" was also a reflection of our privileged place at the edge of real suffering, looking in at a space we wish we could serve more fully.
With our comfort and privilege, many of us feel powerlessness, guilt and sadness in the face of war, trauma, collapse and despair.
"It’s hard to know what to do, how to be of service, what is in my control.... I keep being spiralled back. It’s hard to get out, to find the power and strength."
"I’m sad, scared, cynical. I’m not sure there are enough of us. We’re a tiny part of the globe and life. We need the whole world."
"I feel sad. Orientationless. I’m absolutely stunned in a negative sense where we are. I’m not so sure it’s the right thing to give the crazy fascist autocrats so much attention. We should look at the margins."
At times, the "middle" evoked a circle of belonging.
It is still a rare and precious experience to be together in deeper ways, as we were. To create a space to gather in comfort, refuge and courage.
"Being in a circle that speaks my language. Understanding and being understood."
"It feels important to be together."
"In this time, there's a lot to hold. I don't want to hold it alone. Let's hold it together."
"I came because it’s very nurturing. The depth of connection, participating in person."
"It feels like home. We have a history."
"I feel that I’m arriving as a child, into a safe environment, where I can also be sad and cry or play and jump. It can all be here. There's so much play here. I’m excited but also there’s a fragility and vulnerability to it."
"I’m grateful for even the heavy conversations. We stay together anyway. There is love. It’s lived connectedness."
We recognized that the quality of the relational space is what makes the difference between living life-aligned values or not. We need each other to create such spaces in which we can be held and seen and we can see the many faces of ourselves, the many lenses of life.
"Spaces and times to share like this are so important. We see more. We become more."
"Magic happens in those spaces in between."
Cultivating such a space takes a different set of skills and different ways of being together in "intimate collaboration." These are skills we have as a profession.
And at still other times, the "messy middle" came to represent a fluid potency – something that can't be named but is always present, active, working through us.
We spoke of enlivenment, "enlifement," opening ourselves to deeper forces. Of collective sensemaking and being able to sense into the field. Of "giving ourselves over to not needing to know." Of the values of trust and curiosity. Of channeling something that can’t be named or grasped, possibly something holy. Perhaps it is life itself.
"I’m in awe of the kind of powers we invited and how they were invited to move in us and between us and how they were not owned. Not possessed. That experience where things are liquid, that gives me hope that life will find its way in unexpected ways. This experience of not being in control: nothing is more hopeful than this painful point. This is very precious. Thank you all for making this possible. Thank you to all the intelligences."
The middle was also a crack where something new might break through.
Acknowledging life's own agency and mystery invites humility, we noted, but not so much that we hold back from giving the unique gifts of our profession. Here is where some of us felt the tension between "peace, care, ritual" and "cut the crap, move to action." Some expressed an "itchiness and frustration," a desire to stop talking and "jump into the crack" where the light comes in. "In nature, the cracks are where everything happens. It’s an opening."
"If we can entice a few others into the crack, maybe we can shoulder it apart, like a dandelion or a mushroom through concrete."
"Maybe we can reach out to people not like us, not used to sitting in circles. Maybe more people are ready than we think."
"The work that’s needed is not a red pill or blue pill; it’s a green pill. It’s not like putting vegetables in the soup to sneak them in unnoticed. It wants to be more explicit. Like the maniflexo says: I am no longer neutral."
Here, the middle serves as a call to direct practice: to apply our skills of space-holding, deep listening, embodiment. Of seeing and learning from patterns. Of inviting emotions as guides and designing with care. Of eliciting stories as a way to break through the numbness.
The weaving and the work
I'm not sure we brought all of these interpretations and experiences of the metaphor together into one tidy narrative. We didn't leave with The Answer. This wasn't really our intention.
But I believe some important clarity shone through. My sense is that the work that is needed is not only to be in deep relationality, or to channel and serve life's unknowable potential and emergence, or to be in our individual practice. The work that is needed is to do all of this at new levels of collective practice.
It’s not only about being in the messy unknown. It’s about creating a sufficiently coherent container within which we can draw guidance from that deep well of potential so that we can respond with wise collective action.
Because "the solutions are out there," as one of us said. But they can’t be manifested through working alone or through business-as-usual project management and problem solving approaches. More wisdom is needed. More collective will. More depth. More intelligence(s). More honesty, curiosity and imagination. More courage.
And so, the next vulnerable stage for the field of OD may be to support collectives (projects, organizations, communities) in growing ever more skilful at:
being in deep relationality, in a nurturing circle of belonging
being guided by life's emergent potential, attuning to the unnamed mystery at the core of our beings
cultivating sufficient coherence of purpose, as we turn together towards the pain that calls out to us in the world
so that our actions reflect the wisdom that is needed, breaking through the cracks that are forming in the old
so that, in these ways, we continually learn and evolve toward ever more thrivability.
These are the core patterns of all living systems, nurturing parts, relationships, wholeness and life in unfolding learning and responsiveness. This is the work of "organism development," as we steward and cultivate the conditions for a collective body to emerge, in ever-deepening alignment with all life.
"Every myth has a seed of hope in it," someone at the gathering shared. "There’s a seed of hope in the messy middle."
In our opening campfire circle on the first evening, with the birds chattering around us and the glow of the flames lighting our faces, Ilma Stankeviciute shared an enchanting tale about an old woman who keeps weaving a pattern, and a crow who keeps unraveling it, after which the woman starts again. If the old woman ever finished the pattern, the story goes, then the world would end, and so the cycle continues.
Amid the messy, unraveling forces in our world, what I am taking away is that we are the weaver and the woven. We keep bringing people together, weaving new spaces of enlivenment, and then they are unraveled, and then we create the next weaving, and the next and the next. And in this way, we contribute to life's "enlifement," in ways we cannot fully know. This is our privilege and our noble profession. How beautiful. And how beautiful to be in this together.
With so much gratitude to dear co-hosts Din van Helden, Ramona Fricke and Eva-Maria Spreitzer and to the OD for Life community.
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