I Went on a Self-Directed Writing Retreat and Here’s What Happened

Emma Pickering is a Canadian writer, entrepreneur, and avid tea drinker. Visit her book review blog or check out her online clothing shop, The Moody Maiden.

Whoever came up with the idea of writing retreats is a genius. As much time as you want away with nothing to do except write? It doesn’t even have to be writing—it could be anything. Yoga. Mediation. Art. Taking time away to specifically work on your passion, whatever that may be, is the stuff of gold for anyone with a creative outlet. It’s a valuable, precious experience.

But until earlier this year, I had never been on a writing retreat. The ones I’d heard about always seemed so expensive, or involved applying for a spot that was difficult to get. I figured for me it was an elusive endeavor to be lived vicariously through those that could afford to do it. 

And then, one day back in early April while I was absently working away at my part-time job, it hit me: I could just do my own writing retreat! Duh! 

That night, I sourced an Airbnb that was a three-hour drive outside of my city and booked it for eight days in May. I had a month to go until the retreat, but had no clue how to run one.

So I began planning. 

Prepping for the Retreat

My current goal as a writer is to submit as much work as possible to different magazines, so I knew going into the retreat that I wanted to focus on creating new material and editing old material.

Because of this, I did not do the typical novel-writing retreat. Instead, I focused on poetry, short fiction, and creative nonfiction since those genres would allow me to create multiple short pieces in the relatively short amount of time that I had. It would also allow me to have a larger selection of work to pull from after the retreat when submitting to magazines. 

Tailoring the retreat in this way is the main reason why it was so effective for me. That’s the beauty of a self-directed writing retreat—you can design it to meet your specific writing needs and goals!

The first thing I did was research literary magazines for open submission calls, themed submission calls, or writing contests with free or very cheap entry fees. Some of the best places to find these types of things are Freedom With Writing, Authors Publish Magazine, Submittable, and Literistic.

For any calls I was interested in, I made note of the due date (if any), the reading fee (if any), what they were looking for, the theme, what they paid (if anything), and the limitations for word count and number of submissions. 

Personally, I like to keep all of this info on physical individual pieces of paper for each submission call that I then keep in folders labeled “Submission Calls with due dates,” “Submission Calls with no due dates,” and a current “Work Plan” folder where I keep submission calls I currently want to work on or that have upcoming due dates. 

If a submission call or deadline comes and goes and I didn’t end up submitting to it, then the piece of paper for that submission call gets moved to a folder labeled “Past Submission Calls/Potential Prompts” for future inspiration. 

I know this process is a bit old-school and probably a waste of paper in the end, but it really works for me as I’m a tactile person and like to have the option to lay everything out when I’m looking at it—and you just can’t do that with electronic records! If you like this filing process but prefer electronic, I recommend using Asana to accomplish the same thing digitally. They have a free plan.

Once I had a solid base for the places I wanted to submit to, I then focused on prepping my mindset for the retreat. I did this by creating a list of questions going into the retreat that I wanted to explore such as:

  • What kind of writer am I? 
  • What is my planning process? How do I brainstorm?
  • What topics/themes/genres are easy to write and why? Which ones are difficult?
  • As a writer, what are my personal themes? What do I want to explore and keep coming back to? What am I obsessed with?
  • Do I listen to my writing instinct? For instance, do I try to force a story out? If yes, does it work well? Or do I end up staring at a blank screen for three hours? If it feels forced, do I abandon it instead? 
  • If it’s easy to get a story out, what is it about that process that worked?
  • What, if anything, do I do to get into the writing mood?

All of these questions were geared towards bringing self-awareness to what I was doing on the retreat, which is something I’ve not really done before when it comes to my writing. Usually I would just sit down, start writing or outlining, and depending how things were going I might get distracted or spend too much time looking something up. I never sat back and thought, “Whoa, wait a second. I am doing a writing thing right now. That involves a whole process. What is that process for me?” I wanted my retreat to have not only a creative element to it, but a meta one, too.

The last thing I did was set rules for myself to follow. I decided that on the retreat, I could only do stuff that related to writing. So I could write, edit, read, research writing stuff, or, if I wanted to take a break from reading and writing, I could watch YouTube videos about books or writing. I also tried to not go on social media and set a daily screen time limit for my social media apps. 

There’s one other thing that I did that I highly recommend doing if you’re on a budget. I created a meal plan and then made pre-cooked, prepackaged frozen meals that only needed to be thawed the night before and microwaved when ready to eat. I did this for two reasons. First, because having to eat out everyday for all of my meals was simply far too expensive. Second, because even though I had access to a kitchen and could cook, I didn’t want to be wasting valuable time cooking and washing pots and pans when I could be writing. 

Once all of that was set up and May rolled around, I packed up the car with my laptop, clothes, and frozen meals, and hit the road. 

Here’s what happened. 

I changed my outlook of writing

Within the first day of the retreat, I immediately began seeing writing as more of the business that it is and less of the guilty pleasure/purposeless hobby I’d always felt it had been for me.

Writing creatively is a form of artistic expression first and foremost, and yet I’d always felt guilty for doing it because it can be very hard to validate that what you’re doing is worthwhile. Shouldn’t I be doing something more fruitful with my time? Why am I bothering doing this when it’s probably not even good and no one will read it? All of those insecurities that I’m sure any writer can relate to weren’t just insecurities for me; they were perspectives too, of my own writing and of writing in general.

But literary magazines need readers to read their stuff, right? So they need content. They need your work. They need writers to send them their stuff. They will pay you for it. And that’s what business is. Having those folders full of submission calls were like little work assignments for me to accomplish. They gave me direction. There was something at stake now, in a sense—something to work towards. 

One magazine had a “Fear” themed submission call. I had something to say about fear, so I submitted work to them. Another one had a “Fury” themed submission call. I had lots to say about fury. 

Suddenly, my creative energy and my personal experiences were being turned into material that these places seemed to be calling for. Another place wanted micro fiction under 100 words. I could do that for them. Another wanted poetry of a vivid dream-like nature. Perfect, I would try my hand at that. I began researching the difference between pitching vs. submitting and how it was more business-like to pitch (I’ll touch more on this later). All of these tasks reframed how I saw writing and I figured out in a way that was meaningful to me why and how writing can be a business.

Submitting to all of these places didn’t mean I was going to get accepted by them, of course. But that’s not the point; the point is that I now had the incentive to create new work. And the more material you keep creating, the more you practice, the better you get, and sometimes that’s all you need to want to keep writing, even if the publishing part doesn’t come until later. 

I became a better editor

There was a short story I wrote about a year and a half ago that has been through several drafts and I knew I wanted to do something with it someday, but I didn’t know what yet. The retreat was the perfect time to address it.

In my list of submission calls, there was a free contest requesting short stories on any topic from anywhere in the world. I felt this short story I’d written would be perfect for it, but their word limit was 4000 words. And the short story at the time was almost 6000 words long. 

So I spent one afternoon sitting in a café doing a huge overhaul of the short story. Killed my darlings, as the saying goes, and chopped the story down to just under 4000 words. Doing this process made me such a better editor.

The story was originally written in first person, but I ended up converting it to third person to add some much needed distance. I kept sentences and thoughts relevant and concise so that they served the story and not me, the author. It truly made the story better overall. By the end of it, I didn’t feel I’d actually lost any material that I was really sad to cut out, which makes me wonder what it was doing there in the first place. 

And in the end, the story ended up making it to the short list! If that’s not validation, then I don’t know what is.

I got to stretch the poetry legs I didn’t know I had

Poetry is my weakest genre. I don’t know a lot about it and have always found it intimidating. Every poem I’ve tried to write felt clichéd and amateurish; I didn’t know how to access that place of poetic inquiry that seems to come so naturally to some people. 

But within my submission call assignments, there were free calls for poetry—which meant I had nothing to lose and only experience to gain. So I had a day where I ended up writing eight new poems. And I didn’t hate them! Which was totally a new feeling for me with regards to my own poetry.

I’m not really sure what exactly it was that made me feel differently about my poetry than I had before. Perhaps I was older and wiser, or becoming more artistic. What I do know though, is that having those assignments helped immensely. I didn’t feel self-conscious about writing a poem—like, who do I think I am trying to be all poetic and deep? For once I didn’t see it that way. I saw each attempt at a poem as a potential job offer (again, going back to the business outlook). 

My new poetry-writing process may have also helped, too. I used a blank journal to handwrite the poems first. I felt it gave me more freedom in the creating process, less distraction, and more room to connect to my mind, feelings, and setting. And unlike handwriting fiction, committing a short poem to the page by hand isn’t as daunting as a first story draft. Once I felt okay with the poem on the page, I typed it out and edited it from there.

I know poetry will be the hardest genre for me to publish, but again, incentive to even do it in the first place is progress. And so far I have received helpful and even positive feedback on four poems that I submitted to Furious Gazelle for their Fury theme. They offer $10 critiques that you can purchase when you make your submission. So whether they accept your work for publication or not, they’ll at least give you three lines of feedback for each poem. 

Continuing with the theme of thinking of my writing as a business: I would consider paying for this critique a business investment. This submission process allowed me to become more involved and invested in my poetry than I ever had been before. 

I became more aware of my strengths and weaknesses

Taking a whole week away to focus on just writing really puts into perspective what you’re good at and what you suck at. 

For instance, there was a submission call from Stormy Island Publishing that wanted short stories of the romance-fantasy genre. I actually never completed this assignment because I found out that it’s very difficult for me to write romance or fantasy, let alone both of them combined together. And this caused me to reflect on why those genres are weaker for me. 

I came to the conclusion that my feminist identity kept clashing with what I knew about the romance genre, that is, the heroine has to choose between a guy and her career, or choose between two guys, or doesn’t feel fulfilled in the story until she ends up in a relationship. I wanted to subvert the typical romance clichés but felt I couldn’t if that’s what the magazine wanted.

Then there was the fantasy element. I’m not a huge reader of fantasy because I find the worlds overwhelming and the books intimidating to commit to because they’re so long, and I can be a slow reader if I’m not into the book I’m reading. Having all of those thoughts about the fantasy genre while trying to write a fantasy short story was not helpful or productive. 

On the other hand, I learned that I’m actually not bad at pumping out fiction that’s fewer than 100 words, even in the sci-fi and fantasy genre. I did this for The Arcanist’s microfiction call. I found that centering the story on a pivotal decision that the protagonist must make within those 100 words was the perfect formula for creating a cohesive story with a beginning, middle, and end, which is what The Arcanist wanted. I’d never attempted microfiction before because it seemed impossible to fit a story into that amount of words, but having the time on the retreat to really think about it led me to create three full stories all exactly 100 words. 

Whether or not The Arcanist publishes those three stories, realizing I have a skill in creating microfiction was valuable enough. It’s the type of skill that could come in handy for a lot of things, like other microfiction calls or using it as a tool to plan out pivotal moments in a novel. 

I learned how to create a personal essay pitch

On the retreat, I finally had the time to do a deep dive research session into submitting personal essays. Some of the places I was interested in submitting personal essays and articles to were Catapult, The New Yorker, Bustle, Longreads, Glamour, Allure, Vox, Marie Claire, The New York Times Modern Love Column, and Elle.

My research began with looking at each magazine’s submission process to see if they had anything to say about what they were looking for. Some of them wanted pitches; some were okay with receiving a full draft.

Writing a personal essay pitch was new territory for me. An editor at Catapult specifically has a Google doc about what he is looking for and what he wants in his pitch. I also found a really good article on Catapult’s website about pitching versus submitting and why you should pitch first. 

Essentially, if we’re looking at writing as a business, pitching first makes a ton of sense. You’re trying to sell yourself, get the job, entice them to want to see more. Reading a full first draft is a big commitment for an editor, and there’s no guarantee they’ll like it. You may just end end up wasting their time and making them frustrated, and then you feel bad, too. No one’s happy.

A pitch, on the other hand, is meant to give them the same glimpse into the piece without the time commitment. Plus, if you pitch first and they like it, they may have a specific way or angle they’d like you to structure your draft.

For this particular personal essay I wanted to write, my plan had been to write the first draft on the retreat. I knew it would be difficult to write this particular essay I had in mind, so I kept putting it off. But once I did this research and realized maybe I should actually be writing the pitch first instead, that’s what my new task became. 

Following the Google Doc’s pitch requirements, I wrote a pitch for the essay—and it helped immensely. First, it helped me distance myself from the material, which made it way easier to work on the essay without writing the essay. I now had this rigorous outline to follow and wasn’t allowed to get too in-depth into the piece itself. Second, the pitch allowed me to finally organize the material I’d wanted to write, and the process massively clarified the direction I want to take the essay in. When I do go to write it, I’m going to have a way better idea of how to draft it. 

I remembered why I like creative writing so much

One of my assignments was to create a short story for Jolly Horror Press for their themed submission call of Accursed Item. This magazine wants comedy horror. I wasn’t really familiar with writing that genre, but I went to another café one day and came up with an initial starting point (a witch who sucks at being a witch), and went from there. 

I had no idea where the story was going or what would happen, but I spent a few hours just completely making it up on the spot, finding plot where there was none before. Every spontaneous paragraph built off of the previous one, and eventually a story started to form on the page and developed. 

I think as creative writers, we can agree that this is the crux of writing at its strongest. You can have a story planned out and the themes chosen and plot points decided, sit down to write, and still feel stuck. That day though, I was truly in a place of pure imagination and was genuinely having fun just making up a bunch of nonsense that began to form a story. 

How to make your self-directed writing retreat effective

If you are thinking of doing a self-directed writing retreat, I recommend doing the following: 

Plan, plan, plan

Do the prep work and tailor the retreat to meet your goals and needs. It’s self-directed—you can literally do whatever you want at the pace that’s right for you. Leave the heavy, intensive writing research for the retreat (like researching essay pitching), and do any preliminary research before the retreat (like finding literary magazine submission calls) so that you have more time on the retreat to write.

Set intentions

Go into it with intentions, not goals. Having goals is too competitive and stressful, and may just lead to procrastination if you’re viewing the retreat in terms of “goals to accomplish.” When it’s over, if you find you haven’t met those goals, you may feel like your retreat was a waste of time. 

So I gave myself intentions instead. I intended to work on poetry, creative nonfiction, fiction, editing, and researching pitches. I didn’t set any goals like, “must write at least 10 poems,” “must write at least 15,000 words,” etc. I just set intentions and stuck to them, and that in itself was an accomplishment.

Choose your genres

Decide what genres you want to focus on. Will you work on a novel? A short story collection? Poetry? Being specific about what you’re going to work on will help give direction. On my retreat, I did at one point find it tempting to want to switch gears to work on my novel, but because I had already established my intentions to work on the other genres, I stopped myself and stuck to what I was there to do. 

Change things up

I developed a routine for each day: get up, make tea, have a quick easy breakfast, begin working, go to a café in the afternoon, take a YouTube break in evening with dinner, then research or write some more. But I made sure to change up my location and activities throughout that routine. 

I visited a new café everyday, did yoga, went for a walk in the forest, did some window-shopping, read a book. I don’t recommend working on writing the entire time because you’ll just get drained. So know when to take those activity breaks and switch up the routine. 

Is a self-directed writing retreat the “WRITE” choice for you? 

If you have any kind of serious intentions about your writing—whether it’s seriously wanting to get published, or seriously wanting to finish a book, or just seriously wanting to write more and figure out your process—a self-directed writing retreat is the best first step you can take.

Perhaps the lack of structure of a self-directed retreat intimidates you. Or maybe the freedom to make it your own is highly appealing. All I can say is planning out and executing my own writing retreat was one of the best things I ever did for my writing. 

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