Too Intimidated (or Risk Averse) to Organize a Writing Retreat?

Image credit: https://www.tripreporter.co.uk/new-york-on-the-queen-mary-2/

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This post originally appeared at https://janefriedman.com/organize-writing-retreat/

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In the fall of 2022, I went on my first ever writing retreat, a week in Tuscany in company with ten other writers and two respected instructors. I went with the expectation of generating new words on a new project—and instead pivoted and got feedback on a manuscript draft, which I edited when not in group sessions, group meals, group tours, or taking naps to manage the jet lag. I had an amazing time, enjoyed myself immensely, and got a ton of value out of being with a group and revising existing work.

And yet I also thought to myself, “I would design a retreat differently.” But I felt I didn’t know how.

So I took a workshop on creating retreats that sell to flesh out my idea into a plan and a budget. I focused on the value of what I was delivering in addition to creating logistical line items for food, transportation, and lodging for participants.

And then I chickened out. Faced with the financial reality of putting down deposits for hotel rooms and catering without a guarantee that I could fill the retreat and recoup my investment, I decided to not do it.

But I still had a vision of what my ideal writing retreat would look like.

So I took myself on a transatlantic cruise and called it a writing retreat in the fall of 2023. I had a list of things I wanted to work on during this time. Without any group obligations or schedules, I was able to relax and focus on my work. While having all my meals taken care of! And with limited distractions, as I chose not to participate in any of the ship’s entertainment options during the daytime!

Still too chicken to offer my own retreat, I nagged asked the instructor of the Tuscany retreat if I could coach alongside her on her first cruise writing retreat—and she said yes. The retreat on the ocean liner was structured very similarly to the Tuscany retreat: each day had several group sessions and a group dinner; writers could choose how they wanted to spend their free time on the ship or opt in to one-on-one sessions with instructors. It was a fantastic experience, even though it cost me more to go on the trip than I received in remuneration. I went into it knowing that it was my choice to invest in getting this experience in this way. The payoff for me was being able to work with writers individually (and in the group sessions as well) and see them think of their work in new ways, try new techniques, and find new solutions through our time together. And, down the road, several writers came to me for paid coaching, so that retreat will eventually pay off for me in financial ways.

Which brings us to 2025. Now that I have been on a retreat as a writer, taken myself on my own retreat, and co-led a retreat, can I finally lead my own retreat despite the risks?

Yes!

What changed?

• I have more confidence after having “retreated” as a writer and as a co-teacher. Some of my fears of hosting my own were related to not knowing what I didn’t know. So I was my own guinea pig.

• There will always be things out of my control as a host. I can’t control travel costs or cabin availability or whether anyone will sign up, but I can talk about the retreat where I have a presence and I can talk about the benefits of this particular retreat for writers who are interested in this particular retreat.

• I accomplished a lot on my retreats, even if it wasn’t what I intended at the start—so I can attest that spending time on a retreat is worthwhile.

• I can share my ideal retreat with others, and those who want to experience a retreat like this will choose it. There’s no “right way” to host a retreat: the only right way is the one that excites the host and in turn, excites the right attendees. I’m so excited to be able to bring a cruise writing retreat to those who want to do it!

  • Note: if taking a cruise is a “hell no!” for you, I’m so glad you know this about yourself! 

• Knowing that organizing travel logistics is not my passion or strong suit, I’ve outsourced those functions to a dedicated travel coordinator. This way, writers can pick the logistics that work best for them, and I don’t have to do it or get stuck with a bill.

• There will always be financial risk, but I am comfortable with it. I’ve tried to make the “event fee” (the cost of my coaching) as affordable as I can for the value writers will get. I’m very confident writers will make a lot of progress on their projects before, during, and after the retreat with the planning, accountability, and feedback they get from working with me. I know this going into it: I will break even only if four writers attend. But it’s worth it to me to give this venture a try.

  • Note: the travel deposit and the event fee are refundable up until 120 days prior to sailing, which is the cruise industry standard.

• I can choose how to structure the retreat. I know I don’t want to teach classes; I want to work one-on-one with writers on their individual projects. Which means I really can’t serve more than eight writers on this retreat. Of course, retreats are more profitable the more you scale, but the tradeoff is the 1:1 coaching, accountability, and feedback daily.

I can feel the fear and do it anyway. And so can you.

Don’t forget: I’m leading a cruise writing retreat September 3–10 from New York City to Southampton, England, on the Queen Mary 2! For those who want to spend a week dedicated to their writing projects with 1:1 support from a book coach while traveling across the Atlantic in luxury.