Working Retreat

Plan the work, protect the focus, and let the group help you keep going.

Have you ever thought you just needed to get away for a while so you could work?

I have gone away on my own and stayed in a hotel to work on a project. I have also brought a small group together for a writing retreat. Those were very different experiences.

At the group retreat, I could look around and see other people doing their work. When I wanted a break, their focus helped me stay with mine. We planned, wrote, talked through obstacles, and accomplished far more than I would have expected.

You do not have to be writing a book to use that structure. A working retreat can be for any project that needs uninterrupted thinking and creating time.

Choose the purpose of the retreat

A personal retreat and a working retreat are not the same thing.

When I am alone, thoughts about my relationship with myself tend to come up. That can be wonderful if I have set aside the time to coach myself. I can take walks, journal, do Models, and ask another coach for perspective.

But if I went away to finish a project, that inner work may become what occupies the time instead.

Working alongside other people gives me a different kind of momentum. We are there to create something specific, and the group's energy supports that focus.

Decide which experience you want. You can value both without expecting one retreat to do everything.

Protect three full workdays

For my retreat, my assistant found a beautiful house in Jackson Hole with nine separate bedrooms. There were eight participants and me.

We arrived on one day, worked for three full days, and left on the final day. That gave us five days together, with three days protected from travel.

I did not want someone arriving during the work or thinking about packing and catching a flight while we were trying to focus. Arrival and departure had their own space.

Three days felt like a good amount of time. The limited hours made the work feel important, and the intensity of the focus was challenging to sustain much longer.

You can adjust the length, but make sure the working days are truly available for work.

Take care of the practical details

We hired a chef to handle shopping and meals. Dinner on arrival was buffet-style so people could eat when they arrived. During the working days, meals were ready without anyone having to organize them.

We checked dietary requirements ahead of time. Breakfast and lunch together were optional, while we gathered for dinner.

Everyone stayed in the same house, so we did not have to coordinate people leaving and returning. Each person had their own space.

I also wanted a place where we could gather comfortably in a circle. A table can work, but I liked being on couches and chairs with nothing between us.

The surroundings were beautiful, and being able to go outside for fresh air helped me return to the work.

Use the first hour to plan

On the first morning, we gathered at nine. I explained that everyone needed to decide what they would accomplish over the three days.

What was the project? What were its parts? Which pieces would be completed during the retreat?

Then each person broke that work into hourly chunks and scheduled it. They decided what they would do first, second, and third, and how long each piece would take.

I gave them an hour to make that plan.

People sometimes want to skip planning because they want to get straight to writing. But if you give yourself an open-ended amount of time for one piece, it can take the whole retreat. Planning makes the intended result and the time available clear.

Afterward, we briefly shared our commitments with the group.

Make the work blocks silent

We began with two hours of focused work. No talking, interrupting, or asking clarifying questions. Everyone prepared their drinks and anything they needed before sitting down.

Phones went into airplane mode, and computer notifications were turned off. The work was the only thing accessible.

People could work privately in their rooms, but most stayed in nearby spaces where we could see one another working. That was motivating for me.

Someone needs to be responsible for the timing and the silence. If a group starts whispering and interrupting, the point of the work block disappears.

I was strict about beginning and ending on time. We worked, then put it away when the block was finished.

Coach the obstacles that appear

After the first work blocks, we discussed what had come up. People had thoughts about not being good enough, not knowing what to write, or believing someone else's work was better.

Those thoughts mattered. Writing is work we do with our minds, and the way we think affects our ability to keep creating.

I gave feedback and coaching. People could read a little of their work or describe where they were stuck.

It was especially useful to do this on the first day, because the obstacles that appeared then could affect the rest of the retreat. We could identify them rather than let them quietly run every writing session.

Discussion is optional if you are creating your own retreat, but decide whether feedback and coaching are part of the experience.

Give yourself thinking time

On the second day, I asked everyone to spend twenty minutes thinking before writing. They focused on their project, what they wanted to say, and the ideas they could develop.

The instruction was to keep the brain on the topic. Not daydream about unrelated things or get absorbed in negative thoughts. Think about the work and write the ideas down.

For some participants, twenty minutes felt very long. For others, it felt short. People were surprised by how many ideas they could access.

If you have not tried this, begin with five minutes and build. Sometimes I give myself an hour of thinking before beginning a project.

Thinking is part of the work, rather than something you only do when you happen to feel inspired.

Build in genuine breaks

We had lunch breaks, walks, and free time. I did not fill every break with a group activity.

I enjoy the energy of working with people, and I also need time alone. Letting everyone choose what to do during a break gave us space to return refreshed.

We experimented with two-hour blocks and shorter blocks separated by breaks. For me, a solid two hours was more challenging and more effective once the writing was flowing.

Your group may need shorter periods at first. Decide how many focused hours you want, plan them, and adjust based on what you learn.

At the end of the work, we stopped. We relaxed over dinner instead of continuing to chase unfinished work into the night.

Create the structure, then do your work

I did not fill the retreat with teaching or provide everyone's writing materials. People brought what they used to work. The main instruction was about planning and thinking time.

The power came from doing the work together within a clear structure.

Choose the project, define the result, protect the hours, and honor the silence. Make room for the thoughts and feelings that come up without letting them replace the work.

A working retreat does not need to be a large event. A small group with clear commitments can create a focused, productive experience—and a lovely time together.