How to organize and run a writing retreat (that actually makes money) + 4 things you didn’t know about me

How to organize and run a writing retreat (that actually makes money) + 4 things you didn’t know about me

Last year I shared a castle with some writer friends for Nanowrimo and got featured in CNN.

We’ve decided we like living in castles and want to do more of it.

Specifically, I love how effective I can be with someone when I’m actually in the same room, and can really dig deep and focus on helping them improve their craft, marketing efforts, story structure and author platform. I’m a master idea-generator and love the challenge of discovering the best way to express your message.

I also think writing retreats are a great side-gig for me because:

A) It’s not actually that competitive, most writers retreats are run by semi-professional organizations without much experience actually running events, and/or they focus on the wrong things.

B) I get to surround myself with cool people, live in amazing buildings, and do what I love (helping authors improve their book sales).

HOWEVER, running events as a business is a whole different ballgame. I enjoy it enough to do it for free, but I still need to make sure I charge enough to cover all the costs so I’m not losing money.

Here are some notes to myself, that might also be useful if you’d like to organize your own writing retreat or event.


#1. Choose your purpose

It’ll be a lot easier to attract your target audience if you believe in something. You can’t just get writers together to “do their own thing.” You need to have a vision, about why writing is noble and pure and creative expression cures depression and how cowriting in a group is amazing for productivity and passion.

If you’re excited about what you believe in and why you want to do this, that enthusiasm will shine through and attract people who believe the same things. For example, I believe now is the best time to publish a book, and I love helping authors write books readers love so they can actually make a living with their writing. But you want to be more specific, so you can attract like-minded people, which is important for the sense of community (people have to live together and LIKE each other).


#2. Find your value

You also need to be offering a custom experience that will enhance or improve the writers in some way. You need to provide more than *just* the space. If you’re a coach, editor, cover designer etc – you need something that you’re offering, as an expert, that, only you are qualified to give. In other words, you need to position yourself as a reliable, credible expert that other writers can learn from. Why should people come hang out with you? What will they get in return? Why shouldn’t they just go stay in a hotel and write by themselves?


UPDATE: We’re renting an amazing castle in 2019, and you can win a free spot!

Sign up here to enter. Click here for more details.



#3. Pick a location

It surprises me how many writing retreats are in mediocre settings or hotels, when there are so many amazing places in the world to rent. I prefer castles. There used to be a feature in the Airbnb browsing options that let you choose a “type”. That’s not there anymore, but the search string still works. It looks like this (for Europe):

You can also do it by country:

If you’re looking for cabins, use this:

For chalets you can use

If you’re looking for cabins, use this:


#4. Estimate costs

The average amazing location with at least 5 separate rooms/beds costs around $500 a night.
So if you have 5 guests paying $100 a night, you’d just about cover accommodation.

But you also need to figure out what you’re going to feed them and how you’re going to move them around (it would be more convenient to run one in a small town so they can walk around and explore; if you prefer a rural setting you’ll need to plan trips into town or shuttle people. I rented a bigass black van in France and nearly crashed it a dozen times on all the tiny roads).

You may also need to consider internet (internet at most rural places like castles and cabins is poor – in Europe I rent portable hotspots for each guest and/or bring a bunch of prepaid local sim cards for their phones.

The average cost of a 7-day writer’s retreat is around $2500.

5 people x $2500 = $12500.

Accommodation with 5 rooms = $3500/week (on AirBnB you can often get a bigger discount for monthly rates, which is why we prefer to rent for the month if possible).

If you’re cooking for everyone, $10 per person per meal is a good estimate, so $30 a day x 5 people x 7 days = $1050.

I’d recommend also eating a few meals out or taking turns cooking.
Or, if you don’t feel like cooking, invite someone to come for free if they prepare all the meals.

You also want to factor in your time and energy. Plan things careful knowing you’ll probably overspend.

I think it’s reasonable to shoot for $5000 in profit for a 7 day retreat. But don’t cut corners or focus on higher margins: focus on providing an incredible experience. (Giving yourself a 5K margin gives you a lot of wiggle room for emergencies or unexpected fees).


#5. Make an offer

If you think you’ve figured out what kind of retreat you want to organize, who it’s for, where it will be and how much it costs, you can post the details online and see who wants to join you. If you already have a large platform, you can do something pretty casual. For example, we filled up our Mallorca writing retreat pretty quickly just by posting a quick note about it on our blogs (I think there might be one spot left if you want to come).

But writing retreats are generally expensive and take a big commitment, so you’ll probably need to work harder to get people on board. You can do this with:

  • a nice looking website
  • very clear details about scheduling/benefits
  • great pictures from past events
  • great copywriting / sales copy
  • MORE TRAFFIC (if you’ve set a bigger profit margin for yourself, that also means you can spend more on advertising to get new leads).
  • A video – especially a super cool, professional one.
  • Special guests (invite some people with big platforms to come for free or even partner with you by splitting the profits.)

Luckily, most writing events I’ve seen online are super casual, with poorly designed websites and crappy pictures, which means it’s not hard to be way ahead of the game here. At the same time, you’re basically asking someone to move in with you – so you may need to put in the work of actually building a platform by providing value and getting people to know, like and trust you. Check out the page I put together for

#6. Social proof and credibility

Testimonials are a huge deal; you need some that show you’re a good event organizer and that your guests were happy and comfortable. You need some that show you’re a great teacher/activity leader, and some that focus on practical results – like how much work they got done or how much they learned from you. If this is your first event, you can ask friends or past clients for a testimonial.

When I started my book cover business, I did free work to build testimonials; I’d recommend doing the same for a writing retreat. Keep it simple the first year, split costs with friends and try to break even. Once you have experience and some successful events behind you, you can build a nicer landing page and charge more.


#7. Passion or profit

A writing retreat will probably not be your full-time business. It’s something extra that can build your platform. I like them because I feel icky charging lots of money for online work or coaching (even though I could, I just always feel like I should be giving more). I like them because it’s a new parallel activity/income stream I can do a couple times a year and get a lot of press coverage for. Even if they don’t make money, they give me tons of social proof and visibility. People recognize me as “that castle guy.”

I like having

  • Free content
  • Cheap books
  • Hundred dollar courses
  • Thousand dollar private retreats


#7. Curate an amazing group

This is important – you shouldn’t just accept anyone who’s ready to pay, because one person can severely damage the vibe of the group and satisfaction of all involved.

Let people apply. Schedule a video interview. Do some digging – on their social media profiles. Google them and see what comes up. It can be really hard to tell whether or not someone is a weirdo until you meet them in person. You owe it to everyone to make sure you’ve got a stellar group of supportive, kind people.


4 things you probably didn’t know about me

The other reason I love the idea of doing more retreats is that I’ve basically been training for this my whole life, but it’s been a marginalized skillset for the last decade.

  1. I’m an Eagle scout and have spent about a year and a half of my life living in tents at summer camp – for three summers I was in charge of programming, managing staff and making sure everything was going smoothly.
  2. I ran an industrial kitchen for an outdoor school near Boston, ordering food and cooking for 200 people, 3 times a day.
  3. I started an immersive English camp in Taiwan and enrolled three hundred high school students; I wrote the curriculum, planned the program and hired the staff.
  4. You’d never know it now, but I was the lead in a few high school musicals and painted sets for a Broadway play once – I love crafting experiences by focusing on the small details. And while I don’t sing anymore, I’m pretty comfortable on stage or leading group events.

I’ve learned there are easier, less stressful ways to make money, but I do miss the excitement of getting a lot of passionate people together in an outdoor setting, which is why I’m going to up my writing retreat game. Eventually, of course, I’d like to buy a castle to use as a creative coworking space, or at least buy some property in the Pacific Northwest to make an amazing glamping paradise.



Want to join one of my writing retreats?

Nanocastle retreat Nov. 2017

Mallorca writing retreat Sept. 2017