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15 | The Challenges We Give Ourselves

Writer's picture: Damian RobbDamian Robb





 

I gave myself a challenge. A task to complete in an allotted time. I gave it a name and specifications, gave myself some rules to follow, then I went about completing it. That’s the short version of this story. That’s the version I told myself when coming up with this challenge. But, it turned out, like most things, there was a lot more to the story than I was expecting. There were highs and lows, adrenaline and despair, and, best of all, treasure to be uncovered. I didn’t expect any of that when I started. I just wanted to give myself a challenge. Needed to, even, because, well…actually, let’s do this right. Let’s start with…


Part I - The Backstory


Every week, I sit down with two of my friends to talk about horror movies. We, at least initially, were not fans of horror movies. Avoided them entirely, in fact, due to being the self confessed cowards we are. We were fans of movies in general, and story as a whole, and so as burgeoning writers who had recently ended a podcast we had all co-hosted, were looking for an outlet to further talk about these things we were so passionate about. It was in doing the previous podcast that we discovered our shared cowardice, and so, one day, not too long after it had wrapped, I had a thought; what if the movies these three friends chose to talk about were the ones they had avoided for so long? Cowards talking horror movies. That had a nice ring to it. So, I pitched it to my cowardly friends, Tom and Sean, and they likewise saw the appeal it could have both for listeners and ourselves, and so we sat down together and we came up with the format for our new podcast; Scaredy Boys.


In other words; We gave ourselves a challenge. A task to complete in an allotted time. We gave it a name and specifications, gave ourselves some rules to follow, then we went about completing it.


We have now been doing that podcast for five years and have watched and discussed over two hundred horror movies. It has grown into something so much greater than I ever could have expected. Because we gave ourselves that challenge, we have found some incredible films, and some terrible ones; we have been welcomed by a community that we had previously thought would shun us and then have gone on to foster a subsection of that community ourselves; we’ve given ourselves permission to be creative and then share that creativity publicly; we’ve done live shows, started a patreon and been surprised and delighted by the response, and had innumerable heartwarming communications from listeners. All because we gave ourselves a challenge, and then kept adding to it.


Which brings me to the latest addition, let’s call it a supplementary clause; still part of the initial Scaredy Boys idea but also something new. This once again came from a thought that as soon as I had it, I thought it was a good one.


Tom, Sean, and I are all writers, that’s how we met, a decade ago now, in a Masters of Screenwriting course. With our deep dive into horror now five years in, we have grown to love the genre. To learn about its many hallways and doorways and find the ones we’re happy, if still not a little fearful, to walk down and through. And so the thought was to combine those two facts, for us to each write a horror novella, and then unite the three of them into a novel. A Scaredy Boys Anthology.


Like I said, I instantly liked this idea, not only could I see the fun in writing these stories with my friends but it felt like the natural extension to this journey we had rather ignorantly started five years ago. There was a nice story there, that initially, we had barely seen, watched, or read anything from the horror genre and now we would be adding our own little part to it. But, I also wanted another layer to this thing, a bit more connective tissue for the readers, and ourselves. A way to intertwine our three stories and any others we may want to write together in the future. And so, I thought, they should all share the same geography. If we could together come up with a fictional island that existed in our very real world, then we could plant all our stories there, let them take root, grow, and intertwine and pollinate one another. And so we did.


We gave ourselves a challenge. A task to complete in an allotted time. We gave it a name and specifications, gave ourselves some rules to follow, then we went about completing it.


And so, the writing began.


I had an idea, a visual really, of a body on a bowling alley, naked and dead and what would prove to be the first of many bodies to originate on that bowling alley. So, with very little beyond that, I started writing.


It is a commonly held belief that there are two types of writers; Outliners or Discover Writers. Architects or Gardeners. Plotters or Pantsers. Basically, those that plan and outline and breakdown their story before the writing begins, and those that just begin writing with the intention to discover the story as they go.


In truth, like most things, it is a spectrum, but for the most part I’ve always seen myself on the discovery writer end of that spectrum. I get an initial spark of an idea and then I just want to write and find out what happens. I think it’s the most freeing and arguably fun way to write a story, pure discovery where you feel as much a reader as the writer. At least initially. However, at some point in the process the craftsperson in me will kick in and I’ll want to know the structure of the thing, ensure that I’m following the lampposts through the forest and moving toward an exit, not just walking in circles.


With the bowling alley story, I had begun walking in circles. Or maybe, I had simply stopped in the middle of the forest with no idea where to go. So, I switched hats. I took off my Discovery Writer sun hat and instead put on my Outliner trilby. I plotted out my story and soon realised that part of the problem was that it was likely too big for a novella. Or rather, that the ultimate version of the story, the one that I believed would be most satisfying to better set up and pay off the mystery I had developed and give my characters a more complete arc, was a novel. This was sort of exciting. I could now see my way through the forest and while the journey would be longer than I had first expected, it felt like a journey worth taking. Except, it also left me with a quandary, because I still needed to write a novella for this anthology.


Which brings us to…


Part II - The Doing


While we had no official deadline for the Scaredy Boys Anthology, I was now very far behind even our shimmering and watery one. Sean and Tom were each at least half way through their first drafts and now I was back to not having written a single word, now without even the idea of a story to dive into.


Except, that wasn’t entirely true. In the writing of the bowling alley novella-turned-novel, and with the thought of an island of stories that would grow and intertwine and pollinate one another, I had planted some seeds for a potential future Scaredy Boys Anthology story, one that came from a background dilemma in the bowling alley story that only brushed up against the true narrative, but a potential easter egg for readers to find only when we would release a second or third volume of stories.


I think a lot of writers like to do this, lay seeds for future stories in their present one. It’s fun. In modern days we would refer to it as a shared universe of stories, but in truth, stories have always bred stories. There is always more at the edges if we go looking for it. The reality is that behind the scenes is a whole tapestry and with any given story we are just pulling on a single thread.


And so, it turned out, I did have an idea for a story. Same as last time, it was mostly a visual. This time, a hospital that had been burning for five days straight with no indication of going out. A supernatural fire that perpetually burned without burning and which invited those watching it to enter its flames. But that was it. Just that idea. And an idea is not a story. We need a lot more for that. Mostly what we need is characters, a want, and a reason to pursue that want.


So, with all that in mind, the challenge was born. Namely, just how quickly could I write a first draft of this story? Could I do it in a week? What would that look like? A novella is traditionally between twenty to forty thousand words, so how many words would I need to write a day?


The more I thought about it the more excited I got. Not only would this challenge solve the quandary I had found myself in, ensuring that I had a first draft of my anthology story as quick as could be, but the limitations seemed fun. It would force me to push myself, to find some limits and break past them, and would test another theory I’ve been playing with this year; don’t-look-back storytelling.


As this excitement bubbled, a few final thoughts occurred and the last pieces fell into place. I would have to keep my outliner trilby on for a little bit longer, moving at this speed would necessitate I go full outliner on this one, and to keep myself honest I should do it publicly, make a quick video at the end of every day documenting my progress, or lack thereof, and post it on my socials. Basically, invite people in.


And now the challenge was set. A week to write a novella. Two days of planning, five of writing. If we assumed that the whole story might be around twenty five thousand words, that would mean five thousand words written each day; an insane number but maybe achievable? We would find out. That was the point of the challenge.


So, I made a quick video detailing all of this. It was a Wednesday. I would plan and plot over the next two days, Thursday and Friday, have the weekend off, and then begin writing the following Monday with the intention to finish on the Friday or crash and burn.


For the outlining, I started with character. There are many ways to start a story, many initial inspirations from which the story grows. For me, it mostly comes from an idea. Some clashing of thoughts that interests me and makes me want to show others why it’s interesting. A body in a bowling alley, a hospital fire that won’t go out. Rarely, does it start with a character. Often, I wish it would. Story is nothing without the characters driving them, they are what the story is really about. The ideas, and visuals, and tone, is all just window dressing. It’s the character and their journey that is the true spine of any story. So, that’s where I began, asking myself who would be affected by this hospital fire? Would they want to put it out? Are they benefiting from it? Did they start the fire? Work at the hospital? Are they one of the few who found themselves inexplicably drawn to enter the fire? Through this process of asking questions, I was able to get more and more clarity as to who stood at the centre of this story, slowly pulling them into focus. From there, I was able to draw out their want, the thing that would, at least initially, set off and drive the story, and get an idea of the people and world around them. With all that in place, I was able to next start to focus on the plot. I started broadly, scratching out a basic map through the forest, one that looked like it had been drawn in crayon by a child.


All of that took me about a day. Eight to nine solid hours of thinking and brainstorming and asking questions then forcing answers from myself. That’s what most of writing is, creating problems, then finding solutions, and making a whole lot of decisions. The next day was more of the same, except now I was adding detail to my map. I went hard on the plotting, starting with an arc breakdown, then a chapter breakdown, and finally a beat sheet; each time refining my map until I knew just about every landmark and turn.


Then, my two days were up. I had the weekend for any final thoughts to appear, and on Monday, I started writing.


Five thousand words is more than I have ever written in a single day. Stephen King famously does two thousand words every day, rain, hail, or shine, and this is considered a lot. So more than double that meant I was undoubtedly biting off more than I could chew, but, thankfully, on that first day that number didn’t feel daunting, it felt inspiring. I got up at six am, and pretty much got writing straight away.


The start of a story is, to my mind, the easiest part. It’s setting the scene, introducing the characters, things are fresh and new, it’s exciting. Best of all, it doesn’t yet require connecting everything to everything else, and so there’s a real freedom to the writing. It’s also, even with as much outlining as I’d done across my two days, still full of discovery, and for me that’s where the fun comes in. So, day one went well. I wrote for pretty much twelve hours and was surprised by how much I liked the words I had written. I felt good but also knew that this would be the easiest of all the days.


Day two, Tuesday, a similar start but a very different middle. I would be meeting up with Sean of cowardly friend fame, and his partner Belinda, to watch a movie and do some writing together. Obviously, this would cut somewhat drastically into my writing time but I saw that as only adding to the challenge. In part, this was a test to see how much I can get done in a day, and it’s rare that I have a clean slate to write all day and so I was keen to find out if I could still hit my five thousand word goal with a few other obligations thrown in. The day was a good one. I got some writing done before meeting up with my friends, but only a little done throughout the course of the day, too distracted by their good company. This found me getting home at around six thirty pm with still two and a half thousand words to write. So, I ate dinner and then got to it. I am not usually someone who writes at night. I feel I work best in the morning and that my brain is a lot more soupy once the sun goes down, but, again, the point of this challenge was to test and push against my usual limitations, and, while I definitely didn’t feel as fresh as I would have liked, I was still able to put words on the page in some kind of coherent form. I finished up at ten thirty at night, tired and worn out, but more than pleased with the course of the day.


Day three saw me coming at it like a freight train. This would be the peak of the mountain, hump day. On this day, I should hit the midpoint of the story and then would be heading toward the finish. It also, to my mind, had the highest chance of burnout, so to counter that I put my bum in the chair, got to work and then just kept working. Throughout the day, I used a walk as the carrot on the end of my stick to keep me going and then kept extending the stick, putting off the walk until I got more and more words done. In the end, I didn’t go for the walk until my day was done by which point I had exceeded my goal by having written a massive six thousand words. A huge day but also one that took a toll as my brain was weary and worn out by the end of it. Still, everything seemed to be going great, like I was sure to hit my goal with barely a misstep.


Enter, day four.


At some point in my late twenties, I started getting hay fever. Mostly, it’s not a big deal. I don’t have it as bad as some, and really only bother to take antihistamines maybe five times a year. As it turned out, this was one of those days, and it hit me harder than I had ever experienced before. When I started writing, I had a sniffle. A need to sniff every other minute. Then my eyes started to itch and my head felt fuzzy. All these symptoms grew to mammoth proportions so that they all became impossible to ignore. I got a box of tissues and was soon creating a pile of used ones that exceeded those left in the box. So, I took an antihistamine and kept going. The antihistamine didn’t work. This is just how it goes sometimes, the body learns the trick of a particular antihistamine and so, because we’re lucky enough to have options, you have to go with a different one to keep it on its toes. Eventually, I did exactly that, walking down to the pharmacy still sniffing and congested, now desperate for a release. And I mean desperate. The symptoms had grown to such a degree that I felt a little like I was going out of my mind. My head felt full of static which was leaking out of my eyes and nose. My head swam. I tried to pull it out of the water but because the water was inside of my head I had nowhere to go. All this to say, it was hard to keep the words coming under these conditions.


Maybe an hour after I got my second kind of antihistamine, my symptoms started to recede and I began to feel a little more sane. On any other day, I would have called it. I felt wet and wrung out and had managed to get a few thousand words done, but I had given myself a challenge and I really wanted to go about completing it, so I forced myself back to my laptop and continued working. I scraped across the finish line, more than happy that the day was done.


Day five was also a slog. I think the efforts of the week had finally caught up with me and so energy wise, I was running on empty. Add to this that ending a story is the opposite to starting one. It’s pulling all the threads together in a way that meets and honours all that has come before. It’s the climax, the landing, and it necessitates a whole lot more thought to get it right.


I once more just managed to get my five thousand words in on what should have been my final day, except the story wasn’t done yet. While I had achieved the goal of hitting five thousand words a day for five days, one more would be needed to finish things off, so on Saturday we had a bonus writing day.


It turned out to take another four thousand words to finish this story, making the entire thing thirty one thousand words long. Finishing, I felt happy. Relieved. Excited. Spent. Six days of intense writing, two of planning. And now, there was a new story in the world. One that was admittedly very first draft, but first drafts are the hard part, and so while in time I would rewrite and edit and polish this thing until that first draft roughness was smoothed away, for now I had finished the challenge. Completed the task in its allotted time. Followed my rules and specifications, wrote a story and gave it a name.


Which brings us to:


Part III - The Conclusions


Like I said at the start of all this, there was a lot more to this challenge than I was expecting. I did it mostly as a way to motivate myself to quickly get a story down and because it seemed like a bit of fun, but in reality it was a lot more eye opening than that. It helped me realise just how much I can get out of a day, and that with a bit of focus, the right trigger and set of expectations, then it really does just become about doing the work. Work is work, it demands what it demands, but those demands are often a lot bigger in my mind than they prove to be on the page. So, by just starting without all the surrounding overthinking, by having those specifications and rules to follow, it’s surprising just how easily it can get done. Easy here meaning, just putting one word after the other, slowly and mechanically building out a story, which, while taxing, isn’t as complicated as I can sometimes think it to be. It’s not an impossible puzzle, it’s taking driftwood and building a tower. And sure, that tower won’t be perfect, it’ll be ramshackle and janky, but, as long as it stands, that’s where redrafting and honing comes in.


Which brings us to the idea of Don’t Look Back Writing. This is something I’ve been thinking about a lot this year. So much of, at least my, writing is slowed down by constantly looking back. By overthinking and doubt. By rewriting and editing and critiquing as I go. Something that, I think, only ever hurts the process. The story is unfinished and so why would I try to critique an unfinished product? But it can be really hard to turn off that internal critic, and so to counter that I had the idea of Don’t Look Back Writing, where you write so hard and fast without ever looking back that the internal critic never gets an opportunity to voice their opinion. Don’t get me wrong, that internal critic is necessary, but only after the finished first draft. With this challenge, I finally managed to put this theory into practice. By setting such a high goal for each day, I forced myself not to have the time or luxury to look back. I can only look forward, I could only keep writing, and because of that I achieved exactly what I was hoping for. I built my driftwood tower, and I did so in record time. Now that the theory is somewhat proven, the next step will be to master it. To break previously held habits and click into a don’t look back mindset with every first draft, something that I know will require more practice, and likely more challenges.


Finally, this challenge reminded me of the power of outlining. Years ago now, I worked as a painter, and one thing I took away from painting is that preparation is half the work. If you didn’t patch and sand and clean all the walls before you started putting paint on them, then the final product would look like garbage and you’d inevitably end up doing twice the work to then make it look good. As a painter, I don’t enjoy the prep work, it’s finishing my vegetables before I get to eat dessert. But, I know its value, I know that it is painting as much as actually putting on the paint. With writing, I think it’s much the same. This challenge showed me with a bit of focused preparation, that the writing became a lot smoother and quicker. I couldn’t have written this story in six days without those two days of outlining. Those two days of intense thinking and decision making meant I could focus mostly on the words. I always knew roughly what was coming next and so I just had to think about how best to describe it. There is a power in that, and going forward I want to learn how to harness it better.


The value of completing this challenge proved to be far higher than I ever expected. I hoped to get a story out of it, which I did, but what I also got was a reevaluation of how I work as a writer. It’s left me with a handful of new processes that I now want to spend my time honing and refining, so that I can produce work quicker and utilise my time as much as possible; two things that I felt I hadn’t been accomplishing this year. That’s treasure I wasn’t expecting to find and truthfully didn’t even know I was looking for, but am very happy to have stumbled upon. And it all happened because I gave myself a challenge. A task to complete in an allotted time. I gave it a name and specifications, gave myself some rules to follow, then I went about completing it.


So, that’s that, but there is one last thing I want to mention. Let’s call it:


Epilogue or The Challenges We Give Ourselves


Life, really, is just us giving ourselves challenges. Over and over again. Everyday, we have tasks to complete in an allotted time. They have names, specifications, and rules to follow, and then we go about completing them.


It’s through these self-given challenges that we decide how we spend our time. Whether our challenges include exercise. Or child rearing. Working overtime or leaving early to put some hours into practicing a new skill. Our challenges can see us heading overseas, or getting obsessed over a creative project. Renovating a house, or starting a small business. They can have us doing extreme activities simply because they are a challenge, or see us indulging in a simple one over and over in order to gamify it, to read x amount of books a year, or log x amount of movies on letterboxd. They can have us doing quite literally anything, as long as we decide to do it, give it some rules and specifications, and then go about completing it.


Our challenges help us decide who we are.


I like that. I like the small amount of control it allows us. I like that it is the step between the blueprint of the kind of person we want to be and us becoming that person. I like that all our challenges are inherently meaningless except for all the meaning we choose to give them.


I challenged myself to write a story and then I challenged myself to write a blog about it.


And now I have.


So, thank you so much for reading these Stray Thoughts and until next time, and I think this one goes without saying, give yourself a challenge, give it a name and specifications, give yourself some rules to follow, and then go about completing it.

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