How to start a writing retreat in an organized and safe manner

and whether you actually want to do this.

Hello writer friends!

When you receive this, I will be in beautiful Live Oak, Florida on a delectable vacation. Live Oak is about an hour north of Gainesville—an agricultural swath of Suwannee County that’s surrounded by turquoise-colored natural springs and backboned by the Suwannee river. I have friends who have a horse ranch here and—in addition to putting some serious time in on the porch swing—I’ve come to visit my animal godchildren—last year I helped breed some of the mares on our friend’s property and now I get to meet their foals. Watch my Instagram feed for baby horse cuteness!

I’m gearing up to run more classes and destination retreats in 2024 under my Turning Points brand, and in this preparation, I’m remembering the times that people have asked or emailed me: “I want to do this; how do I do this? How do I start a writing retreat?”

I’m going to give advice on this matter, but before I do, I want to put my advice into context. In 2016, I founded a nonprofit learning collaborative for artists called “The Cabins.” We run group retreats roughly twice a year and also pair deserving artists with work spaces in beautiful/inspiring areas. (The Cabins is currently on hiatus— we don’t have offerings at this time.) This year, I founded Turning Points— which unlike The Cabins, is only for writers (The Cabins is for any type of creator) and is not a 501c3. So the advice I’m going to give is based off my experience in these two areas— the nonprofit, and the for profit space.

Our incredible inaugural Turning Points group in New Mexico this October, 2023

Even if you have no desire to start your own retreat, this post might make you think differently about which retreats to apply to yourself. There are DIY writing retreats popping up all around the interwebs, and it’s worth doing a little research before applying (and paying) for them. Are they incorporated as something? (LLC, S-Corp, 501c3) or is this just something the retreat leader is organizing through Venmo? Does the leader have any training in mediation if things go awry? Have they led a retreat before? What’s the cancellation policy if you get sick and can’t attend?

Anyway, here we go— my big picture thoughts on starting your own retreat.

1. The DIY retreat with friends versus an organized retreat with strangers

There is a big difference between renting a house and inviting friends to stage a write-in with you and leading an actual retreat. In the former example, you basically rent a home somewhere inspiring, ask your writer buddies to join you, make cooking and carpool arrangements, outline a general schedule of the day (when are we writing, when are we hanging out), you split the cost for the rental and that is that. You don’t need to be incorporated to do this, and you don’t generally need waivers especially if you’re renting through Airbnb or Vrbo where a waiver is part of the rental agreement. When you go somewhere with friends, you know what you are getting into because you know these people: they are friends. Things get more complicated when you are retreating with strangers, which is why I’ll only be focusing on this second scenario: a proper writing retreat that people you don’t know apply to (and that you are leading in a certain capacity)—for the rest of this post.

2. Protect yourself through incorporation

When I founded The Cabins in 2016, we didn’t have non-profit status. In fact, when I was gearing up to run it, I didn’t have anything by way of incorporation at all. I had myself and skills and background in event management and a good rolodex of people that I hoped would apply, but it was just me, Courtney, running the retreat. I had lunch with an intelligent friend who put down his French onion soup and stared at me when I told him what I was doing. “So you’ve rented a home by a lake in the winter and are going to be housing people you don’t know. What if one of them goes onto the ice and falls through? Gets lost in the woods? If you don’t have at least an LLC, if they sue, they are suing you—Courtney, not an entity—which means they could take your house.”

I hate thinking about liability and litigious issues in general. It’s pessimistic and very American to assume that everyone is out to sue each other for all they’re worth. But worst case scenarios do occur, and when you are inviting strangers into a program, you have no idea how they will act (or retaliate) under stress— and the same is true for their extended family. So you do need to protect yourself against worst case scenarios. I got an LLC set-up quite quickly for The Cabins, then later rolled it into my S-Corp, and then our nonprofit status came through. What that means is if something goes quite wrong during one of The Cabins’ retreats, it will be the entity of “The Cabins” that is being fought, not my personal assets. There is distance now between me and the program. That doesn’t excuse me to act however I want, of course not—I’m talking about distance in terms of liability.

So if you are going to be working with strangers or retreating with strangers, especially if they are paying you to attend, you should incorporate as something to protect yourself. And them!

3. Everyone should sign liability waivers before they arrive on site

In the beginning of The Cabins, I had people sign waivers when they arrived. Sometimes they’d take them back to their rooms and I wouldn’t actually receive them until a few days later. In my baby years, I didn’t see this as a problem. Now that I’m a hardened 45 year-old, I do. Have people sign the waivers electronically before they leave for your retreat.

4. Understand the audience you want before you open applications and use the application form and appropriate price points to reach that audience

You need to have a point of view on the type of people you want attending your retreat. Are you dying to go to Italy and write all day and then have wine and lots of yummy food at dinner? Fine— then you’ll probably be looking at a target audience with roomy pockets who are a little hedonistic. In your application, you have to disclose that wine-drinking/wine-tasing will be a big focus of the program, less you attract sober people who are interested in writing and in Italy but didn’t realize this would be a Bacchanalia of vino veritas.

The application itself is an incredible tool to help you attract your target audience. (I’m talking about attracting the right kind of people in a “vibe” sense; I’m talking about personality types. It’s illegal to discriminate against people for things like race, gender, sexuality, religious beliefs—but I can discriminate against someone who sounds like they are going to be an oxygen-sucker, disruptive, or toxic to the group dynamics, just as I can reject applications of people who don’t appear to be ready for the realities of the region where the retreat is taking place—for their safety, and mine!)

For example, The Cabins takes place in a part of Connecticut with ticks. We have a question on our application that basically says “Litchfield County has ticks in some abundance. How do you feel about ticks?” The responses to this question helped us separate the people who had some maturity and education around tick protection from those who would sue us if they didn’t do a recommended tick check and got bit by a tick.

Similarly for Turning Points (which was in the middle of nowhere New Mexico on a cattle ranch), there were far less questions about the applicant’s writing than there were insistences that the WiFi was really, really bad, that the cell phone signal was shady: how did this make the applicant feel about attending? As a retreat leader, if your memoir is a mess, I can help you. But if you’re going to have a nervous breakdown because the WiFi is too weak for you to post a reel to Instagram, I can’t help you. And I don’t want to get myself into situations where, as the mentor and the group leader, I can’t be of help.

So make sure that your application page is totally clear about the kind of person the retreat might not be right for. (For Turning Points, I warned people about the retreat center’s isolation and deep quiet at night, of the totally unreliable WiFi, volatile cell phone network, impossibility of “popping out for a coffee” (the retreat property spanned 70,000 acres with nothing but tumbleweeds and stunning scenery—the closest Starbucks was two hours away), and the possibility of seeing snakes and spiders on the ground.

5. Paywall applications

The Cabins is a free to low-cost program— most people attend on scholarship. Accordingly, I didn’t want to paywall applications—that felt out of step with our mission. But lo and behold, when I didn’t paywall applications, I got all kinds of nutty spam—lots of people emailing wanting to rent “our Cabin” thinking we were operating an Airbnb. I also got a lot of correspondence and applications from people who wanted to “teach” or “perform” at the retreat, which isn’t an option.

It doesn’t have to be a lot of money—we currently charge around $6 to apply to our programs—but having a paywall helps people take your program seriously and will vastly reduce (or eliminate completely) spammy applications.

6. Pay someone to help you meet your professional and artistic goals

Another reason I started out with everyone applying to The Cabins for free via email was that I had no idea how to create an application system online, on my own. I still don’t. I had to hire someone. This is a great mark of maturity for me—recognizing that I sometimes have to pay professionals to meet my own professional goals. We run applications for our retreats through Squarespace and Stripe. For some reason, the applications arrive in size 8 font via Squarespace, which is highly inconvenient, but otherwise, I’ve been happy with this set up. If you aren’t a tech wizard, find someone who is to create a streamlined application experience for the application writers and the application readers, alike.

7. Make a database of who applied, who was accepted, who attended, who dropped out, etc.

At some point in the early Cabins years, I wanted to send out a Cabins newsletter to everyone who had ever applied to The Cabins, and I realized I couldn’t do that. While I’d kept email lists of all our attendees, the names and contacts of people who had applied, but hadn’t been accepted, only existed in my email. It was a royal pain in the ass to retroactively organize everyone into groups. Keep track of applicants from the get-go in a spreadsheet.

8. Bookkeep within an inch of your life

Money in, money out, who/what it was allocated to—keep super detailed books. I wrote most of my stuff down on Post-It notes in terrible handwriting and my husband (who does our accounting) wished me dead at tax time.

9. Make things a professional-looking as possible

Give your retreat a name (and make sure that name is available), pay someone or bribe a friend to create a logo for you, consider setting up an Instagram for your retreat, and once you start to have applicants and participants, start a newsletter. Gather testimonials from everyone who attends and use them on the website and social media (with the participants’ permission). Get branded notecards from Vistaprint to use as thank you notes for people who helped you or donated to the retreat. Keep your out of office up-to-date and use an email that is separate from your personal email for all retreat business.

10. Understand how you can (and can’t) get donations

Unsurprisingly, people are more likely to donate to a program if it’s tax deductible for them. For donations to be tax deductible, you have two choices:

a) You need a fiscal sponsor

b) You need 501c3 status

I started off with a fiscal sponsor. A nonprofit here in my town agreed to be The Cabins’ fiscal sponsor, and— generously— they said they wouldn’t take a percentage of our incoming donations for themselves. (Usually a fiscal sponsor will take between 5-10% or whatever is coming in to cover their own costs.) The entity only agreed to be our fiscal sponsor when I committed to applying for nonprofit status. They did not want to be our fiscal sponsor indefinitely. We share the same bank in town, so they simply set up a bank account for us within their account, so accessing our donations was actually really easy. Today, now that we’re a nonprofit ourselves, we make donations to them when we’re able to to thank them for their help getting us off the ground.

11. To 501c3 or not?

Whether you should go for 501c3 status or not deserves its own post. It takes a lot of time and paperwork to get the application out, and it can take a lot of time to be approved.

Big picture, the pros of the 501c3 are that you become a tax-exempt entity and that you can not only accept donations but also apply for grants.

The cons? You will need to get your shit together, bigtime, to become (and stay) a 501c3. You’ll need a board, will need to hold regular board meetings and keep minutes, file annual reports, and keep impeccable financial records. I’ve personally found it extremely challenging to be a soulful art witch and an anal-retentive accountant at the same time, which is why you must pepper your board with people who have skills that you yourself do not possess.

12. Applying for grants as a 501c3

One of the reasons I applied for nonprofit status is I wanted to be edible for grants at the state and national level. I only did one round of grant writing, and it was enough to break me—I didn’t do another round again. And I even hired a grant writer to help! One problem is that a lot of our grant money landed in 2020. Remember that year? Remember the pandemic? We couldn’t hold group retreats in 2020 so we were sitting on all this money unsure what to do with it, and nearly all grants have a time-cap. You have to use the money in a certain time frame or you have to give it back.

To successfully navigate grant cycles, I think you need a paid grant writer on staff and also an accountant. We didn’t have the resources to have anything other than consultants in these arenas (with my husband working as our unpaid accountant) and it made everything harder and messier. After our first grant cycle, I seriously considered shutting the entire program down— that’s how scarred I was by it. (And we got grants!)

13. Figure out the food thing before anything else

In my twenties I worked as an event manager and continue to fall back on the organization skills and lessons I learned then. One thing I’m sure of is that if people aren’t satisfied on the food front, it doesn’t matter what level of instruction you are offering— everyone will be crabby and the retreat will suck.

Next to grant writing and fundraising, the whole “food” thing has been the hardest part of running The Cabins. Since most people attend on scholarship, we had barely any budget left for food, and for whatever reason, nearly 90% of our attendees had food sensitivities, making it extremely hard to menu plan. A big part of The Cabins is community involvement, so we had neighbors and friends preparing meals, dropping by with bread, flowers, sweets, and even hosting dinners. It was great fun but it took me about 7 months of planning and prodding and reminding and sourcing to feed 9 people for 4 days.

Turning Points has been much easier to meal plan for because that program is not a nonprofit, people pay a premium to attend. But in return? We give them the former executive chef of the freaking Los Poblanos— one of the finest hotels in the country, and the chef’s assistant, a professional hotelier and bartender. Everyone’s food preferences and sensitivities were handled by a skilled chef who was being properly compensated for his efforts, skill, and time, taking the entire “food question” off my plate so I could dedicate myself entirely to my writers and their writing. HIGHLY RECOMMEND.

Turning Points New Mexico will take place from Oct 20-26th in 2024. Applications will open near the end of March- please follow @turningpoints_writers on Instagram to stay in the loop about program details and application info.

14. Make sure to personalize your liability waivers to the nature of your retreat

Following off the above, an insurance agent who visited a nonprofit conference I attended told me that if meals were being donated to The Cabins and cooked off site by others, that I needed to include a line about that in our waiver in case someone got food poisoning from one of our donated meals. This depressed me, but I did it— we now have a line about “participation in group meals” on our waiver.

Similarly, for Turning Points, there were a lot of potential hazards with the property: there are horses, cows, spiders, snakes, great heat, strong winds, et cetera. The liability waiver for that one was very Wild West.

15. Don’t start a retreat until you’ve attended a lot of them yourself

In my experience, it was helpful to have attended writing retreats as a student and a teacher to better understand what worked and didn’t work in a retreat. What did I want more of, less of, what wasn’t offered or supplied that should have been? Many retreats, in my experience, either suffer from too much scheduling or too much downtime, so I’ve tried to create a really healthy balance between free time and scheduled time in my retreats. I also think a fireplace or fire pit is essential—but that’s just me.

16. Decide on the big A question— alcohol

You don’t want to run retreats that make people feel excluded or uncomfortable for any reason—and one way to make people uncomfortable is to have what was meant to be a mature and productive writing retreat turn into Burning Man.

Give a good hard think to the kind of retreat you want to run: what role with alcohol play? My experience is that when wine and alcohol is available, writers go nuts with it. Even when they say they want to have a demure and healthy retreat, something happens when writers get together (at Turning Points, we have decided that this grouping is called a “Vice” of writers) and people get giddy and excited and happy to be together with likeminded people, and they go hard on the party front. Which might be okay if everyone is in party mode, but if the partying is making other attendees uncomfortable, then you have a problem.

Definitely let applicants know on the application page if alcohol and wine will be making a presence at the retreat, and if you have a sober person or someone in recovery joining you, work with them to understand how to support them during the retreat, or consider making the retreat an alcohol-free zone.

17. Keep in touch with people after the retreat

Whether it’s through a newsletter, group text, private Facebook group, Slack, Zoom calls, or actual reunions, I like to think of all my attendees as “alums” and as a part of our growing retreat family. It’s been a joy to keep in touch and also to connect past participants with new partipants for collaboration opportunities and friendship. The illustrations in my third novel COSTALEGRE were created by a Cabins alum, Dasha Ziborova, who is one of our board members now!

18. Probably host your retreat in the country that you live in?

Disclosure: I have a friend in Mexico with a bonkers beautiful house where I am dying to host a retreat. But the idea of taking strangers out of the country to a place where I, as the retreat leader, don’t master the language, feels insane to me. Also fiscally, it’s kind of a mess accounting for money earned (and spent) in a foreign currency.

I don’t have the courage to take people out of the country at this time of writing, but if you do, go with God and up-to-date passports. If you’re applying to a retreat out of the country, I’d make darn sure that it’s well run by people or (better) an institution who can come through for you professionally if things go wrong. Let’s say your passport is stolen. If you’ve gone on a jaunt with Cindy the retreat leader who’s only in Tuscany to write in her journal and drink gallons of Sangiovese, Cindy probably isn’t going to be able to help you get your passport back, is all I’m saying. Whereas if you’re traveling to Paris under the umbrella (and incorporation) of a university, they probably have contacts in place to help navigate participant emergencies while abroad.

Our phenomenal cooking team, Daniel and Mel, will return to Turning Points New Mexico October 20-26th 2024. Applications will open near the end of March. More info soon!

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I think that’s all for now!

If you have specific questions that I haven’t addressed here, post them in the comments and I’ll do my best to answer them when I’m back from vacation.

In the meantime, I wish you all a happy, healthy and relatively calm holiday, if such a thing is possible? My memoir THE YEAR OF THE HORSES is still 50% off with code MOREJOY through Bishop & Wilde if you need a last minute gift! (Or a New Year’s gift— which I personally love as a concept!) More info about that promo is here.

Thank you for being here. All of my holiday wishes from my family to yours,

xo

Courtney