Starting Your Own Retreat: How Hard Can It Be?

January 24, 2023 § 14 Comments

I guess that guest didn’t hate me after all.

By Allison K Williams

Writers often thrive in new places—residencies and retreats that allow us to expand our ideas and make big progress outside the demands of daily life. But residencies are often competitive and retreats expensive. After eyeing promising opportunities that may be distant, outside your childcare capacity, or require three references (on paper! In the mail!) you might ask, Should I just lead my own retreat? How hard can it be? You’d get to pick convenient dates, cover your own travel, maybe even profit.

After leading sell-out retreats online and off, I can say it’s hard the first time, and new challenges arise from new locations and types of event. But repeat events become a checklist of specific tasks I know I can accomplish. Whether in Tuscany or onboard the Queen Mary 2, I’m going to teach how to finish books and write better, addressing the experience level and needs of every writer present. Most new challenges are logistical.

Going virtual? The new challenge is “make it feel like a real retreat,” and meeting it means gift boxes, responsiveness outside retreat hours, and clear guidelines for participants to plan their time.

New venue in Costa Rica? “Communicate serious dietary needs to the on-site chef in my very weak Spanish.” Hello, Google Translate and a poster of guest pictures clearly marked Vegana, Sin Gluten, and Sin Alcohol.

New itinerary in Portugal? “Schedule tour bus and trains.” Doable with a TaskRabbit helper in Porto, a guide in Coimbra, and the national train system website.

Retreat leadership has evolved from hoping I’d break even and enjoy the experience, into a regular income. It’s truly amazing to nurture artistic growth and exploration in writers who happily contribute to my livelihood. Often, I’m lucky to have Brevity’s editor in chief Dinty W. Moore as co-teacher, which means not only sharing the emotional load but learning new elements of writing myself, in the classes he leads.

Could you create a retreat?

Yes! Even if you start small, perhaps an AirBnB weekend with one writing friend, asserting time for the joy of writing feels great.

But should you create a retreat/workshop/event that other writers pay you for?

Yes, if you keep two main principles in mind.

1) Find the right audience. It’s much easier to market to a specific, defined participant you want to serve. When I created Rebirth Your Book, most retreats didn’t focus on whole-book work. When Dinty and I created our Virtual Intensives, most writing workshops didn’t offer an affordable week focused on one topic.

Are you drawn to help authors fill in the gaps to make their book publishable, or generate new material? Do you want to only offer writing, or explore a new culture, a complementary artistic process, or yoga? Got a great location you want to share, or are you more comfortable over Zoom? As you define your offering, narrow your audience. Instead of “anyone who has a week off and wants to go to Provence,” identify an immediate, pressing problem you will help your guests solve. Market your retreat to people who have that problem badly enough to make time, find the cash, and get there. Be ready to deliver 100%—after their time with you, their problem should be solved.

2) Remember that you aren’t a participant. Retreats are rarely “fun” for the leader. They’re often joyful, meaningful, and profitable, but come with daily, constant responsibility. Having a great time on a mountain hike? Make sure you’ve spent a few minutes walking and talking beside each guest. Check in with the guy who was working through a new idea after dinner—how does he feel about it this morning? Is the lady who needed to reach her family for an emergency able to focus on her writing or does she need some personal time?

Retreats demand rigid flexibility. You must create a strong frame within which absolutely anything might happen. Where you’re truly open to accommodating what each guest needs, even if what they need isn’t what you planned. My first-ever retreat, one writer didn’t want to stay in the venue after all, instead commuting from a hotel and eating on her own. I tamped down my fears and made myself available for porch talks and reading pages on her schedule. She later thanked me for “supporting the retreat she needed to have.”

At another retreat, a writer outlined ideas, but didn’t write much at all. I worried he secretly hated me, was sorry he’d paid me, had only tagged along to be with his friend. But two years later, he booked another retreat, so I guess it didn’t suck—and it’ll be my job again to support the retreat he needs to have.

Sharing what you love in a fabulous location with happy guests is truly marvelous. Taking home a paycheck (and a bit of paid vacation) is the icing on top. With planning, confidence, and clear expectations, you can make great retreats happen—whether it’s just you and a friend, or a fellowship of inspired, productive writers. Whether you break even or make bank, our true profit comes from experience. Our true leadership is taking someone’s hand and asking, “What do you see? Show it to me.”


Allison K Williams is Brevity’s Social Media Manager, and the author of Seven Drafts: Self-Edit Like a Pro from Blank Page to Book. Her retreats take place around the world and online, and she’s offering a webinar about leading your own sell-out retreats (and making a real income from meaningful events) Feb 4th. Find out more/register here.


§ 14 Responses to Starting Your Own Retreat: How Hard Can It Be?

  • I love going on writing retreats. Interesting to learn more about the behind the scenes

    • Allison K Williams says:

      It’s been fascinating knowledge to acquire! It helps that I spent a few years as a corporate event planner, too.

  • Twenty years ago, I attended a retreat on the other side of the country. A few days before the end of the week, my husband called because my mother had collapsed and been transported to the city for spinal surgery. The organizers of the week were entirely unhelpful. They did not know how to get me to the airport to fly home early. There might be bus service? They were too busy to help.

    Did anyone check if I was okay? Not that I recall. Looking back, I should have been angry at their lack of concern, but I was only frustrated and worried about my mom.

    This would not have happened on your watch.

  • So funny, i opened this post on my solo retreat, in a motel in Glenwood Springs, Colorado, which has an amazing and famous huge hot pool and good restaurants. I’ve come here with a writing friend but this time i needed to touch base with myself and didnt want to spend time talking, fun tnough it is. I have often gone to motels to get away from my usual self and work. I’ve been to many artists’ colonies where i made good friends– or not.By the time you apply to such a place, wait months to hear, abd get there if– a big if– you have been accepted, you might as well jump in your car or bus or train and just go and write. My current motel has a lovely desk and desk chair and breakfast comes with the room. Not right for everyone…

  • equipsblog says:

    Three of us recently began a semi-annual one day poetry retreat at new Retreat Center in the Blue Ridge Mountains. We are lead by a talented self-published poet and the format is evolving in response to attendees feedback. So far it has been enjoyable. We begin are second year (and third retreat) during National Poetry Month in April.

  • equipsblog says:

    Thanks. We are enjoying it and most of the attendees seem to like it too. We charge a very modest $10 registration fee. I have hope that we can expand into a weekend since the retreat does have rooms that could be used.

  • Sue Repko says:

    Allison — this post and your upcoming class on how to create and fill up a meaningful retreat could not have come at a better time for me, as I try to enter this world. Just signed up!

  • Sandy Bliss says:

    Hi, Allison! re: today’s post on Brevity, I just organized a retreat for one of my small writing groups: we were 7 women. It became 5 women, then 4 who could go. We rented my friend’s VRBO property, a beautiful home I’d been spending time at for 20 years. We had a great 4 days of writing.
    We had planned to write all day, and watch craft videos after dinner. Instead, we wrote from 10 to 1, then from 2 to 4:30, then played word games and hung out, talking until the wee hours. We all prepared fabulous meals for each other.
    My own writing goal was to take my first draft and work through your book, Seven Drafts. I did the exercises for the Second (Story) Draft, which I’m now hoping to finish by 2/10 so that I’ve at least touched the Character Draft before I take a master class at the SF Writers Conference. on Characterization on 2/17. I’m getting a lot out of your book, for which I thank you. It’s extremely helpful to focus on one area of craft per draft (a rhyme!). Otherwise, it’s too amorphous for me to know that I’m actually doing everything my story needs. (You may quote me.)

    • Allison K Williams says:

      Wow, Sandy, I am so honored to be a small part of your writing process and so glad the book was helpful! Your retreat sounds wonderful and I’m glad you all had a great time 🙂 And yes, I’ll quote you!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

What’s this?

You are currently reading Starting Your Own Retreat: How Hard Can It Be? at BREVITY's Nonfiction Blog.


%d bloggers like this: