Behind the Scenes: Getting Ready for a Writing Retreat: Overplan, Then Let Go

Over the past two weeks, Evelyn and I have sat and talked through the different phases of our upcoming retreat. We’ve reviewed the three sections of the retreat that I first developed with my friend and colleague Nancy London: Grieving, Uncertainty, and Transformation, the rough stages involved in integrating major life changes.

During the first two days, we’ll do everything we can to normalize grief and loss as natural parts of life. The middle days will be devoted to the dark night of the soul—the time our lives come undone and we feel adrift, lost and uncertain. And the final days will focus on integration and the birthing of something new out of what has been lost.

We will stress to our participants in the opening ceremony that things are never that tidy in real life. People coming to this retreat are grappling with huge life changes: ending a career; moving; divorce; the death of a child, parent, or spouse; illness; disability; betrayal; the whole gamut of losses we grapple with during the course of our human lives.

This six day retreat will not provide people with a quick or easy fix, but it will give them a map of the territory, a place to grieve and mourn in community, a safe space to tell their stories and be heard. It will end their isolation and give them a pathway back home to themselves.

During our preparatory days, Evelyn and I have reread dozens of poems and writings from sages, great poets, and spiritual teachers. We’ve spend hours sorting through these materials—picking and choosing—coming up with evocative writing prompts and poems—basically creating a flow that makes sense.

And you know what the truth is? I’m glad we did all this preparation, but there’s a good chance at any given point in time that I’ll toss it out and change gears completely.

When I first started teaching, I overtaught. I wanted to give people their money’s worth. I tried to cram in lots of information so they’d feel they got value from my classes. But in reality, information is secondary—with writing what matters is the process and the insight the writer brings to the page. Time to assimilate and digest is as important as time to write and read out loud.

Over time, I learned that the best teaching is about being nimble and responsive, paying attention to “what is happening on the ground” in the hearts and minds of the participants. Being adaptable. Being flexible. Being willing to wing it in the moment. To trust my intuition about what the group needs. There are times people are wrung out and need help getting grounded; other times they need to expend energy and dance. Maybe the best thing to do is drop my agenda and invite everyone out into the moonlight. Plans always have to play second fiddle to what’s happening NOW.

And that’s what I truly love about retreat teaching—the magical synergy that happens. It’s conducting the orchestra. It’s all the surprises. It’s showing up and being present. And it’s watching the beautiful unfolding of all the people in the room.

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