The Long Conversation
This is your time and space to sit with complexity, play with it, and find experiments to run when you go back home.
Not a deadline, a deliverable. Now slide decks. Your time and space, and someone who knows how to hold both.
The Residency is a three-day working retreat for leaders and creative professionals who feel motionless within a transition, decision, or question. You bring that to the conversation. We talk, play, and craft the next best steps.
What this looks like
You come to coastal New England. The first half-day is for arriving — a walk, a conversation, the slow work of stepping into uncertainty. The second day opens you up. Deep conversations, making things with our hands, thinking on paper, sitting with hard questions until you feel the why in your body. There is quiet time for you to write, reflect, or just be still. The final day is for noting what has emerged, choosing the next best thing, and a farewell when you're ready.
The agenda is yours and the container is mine.
I don't come with a curriculum. I come with decades of experience facilitating complex conversations, a deep practice in improv and systems thinking, and a genuine belief that you already know more than you think you do. My job is to help you hear yourself more clearly.
One client, deciding between launching a new venture and taking a senior role in a large organization, described our work this way: "Our conversations are clarifying what's important for me." They made their choice. A year later they made a different one. I think both were right.
The shape of it
Day one — You arrive. We take a walk. Have an opening conversation. No agenda. Just beginning to decompress and orient.
Day two — We work. Fully. Walking and talking, making and reflecting, mapping and sitting still. Mornings tend to go deep. Afternoons tend to open up. We follow what's alive.
Day three — We surface what has emerged. You pick the next best step. A farewell breakfast or conversation. You leave when you're ready.
An extended version — two full days plus arrival and departure — is available for those working through something that needs more time or depth.
Who this is for
Leaders and creative professionals at inflection points. People who are good at their work and uncertain about what's next. People who think well in conversation and need a thinking partner who can hold complexity without trying to resolve it prematurely.
You don't need to arrive with a perfectly formed question. You need to arrive.
Investment
$15,000 — $20,000 depending on scope and travel.
To begin a conversation about whether The Residency is right for you, reach out at chad@playingwithcomplexity.com