🍻 On Midsummer and Other Challenges
So, is this another fail? Absolutely not. No morning flare? No morning shift. That’s not a fail, that’s just a seasonal shift in schedule. #piratelogic
Happy Sunday, Messmate!
You’ve arrived just in time. The firepit’s still warm from last night, the drinks are (mostly) still cold, and someone – probably Hemingway – has chalked “Challenge Accepted” in suspiciously smug lettering on the back of Sir Bear’s chair.
This week’s Tarts and Tipples Society gathering at Smugglers Cove comes with a slightly singed report from the frontlines. No, not a war zone (unless you count the state of my writing desk). I’m talking about challenges.
Why do we keep signing up for them?
What do we actually get out of it when they inevitably fall apart or spark new fires entirely?
And why, when the heat of summer fries both brain and bandwidth, do we double down on creative quests?
Pour yourself a glass of something sparkling (or caffeinated) and settle in. We’ve got a lot to talk about.
Lurking in the shadows won’t get you anywhere.
Come claim your Deck Pass like a proper pirate.
Challenge Accepted?
If you’ve been aboard Resilience for any length of time, you’ll know I have what one might charitably call a challenge addiction. At any given moment, I’m juggling at least two creative gauntlets – sometimes more if I’m feeling particularly reckless, or if the universe decides to throw a shiny new opportunity my way.
Right now, for instance, I’ve just completed two, but I’m still neck-deep in it. I have the romance-writing challenge, the can-I-write-a-book-with-AI challenge, and the write-25-love-stories-for-Christmas challenge. So why not pick up a write-50-ghost-stories-for-spook-season challenge while we’re at it?
Oh, and I almost forgot – there’s also the attempting-to-redesign-our-entire-Substack-strategy challenge, because apparently I thought the summer season was the perfect time for a complete platform overhaul. Because why do one impossible thing when you can do several at the same time?
I guess one answer is that us creative types are drawn to challenges like moths to the flame. Even when we know there’s a fair chance we’ll get our wings singed. There’s just something about a challenge that scratches an itch that regular (writing) routines simply can’t reach. It offers a fixed term structure when we’re drowning in possibility, a sense of community when we’re isolated in our writing caves, and that delicious pressure that transforms “I’ll write something, eventually” into “I must write 500 words before breakfast or [face public shame].”1
But it’s not just us creatives. There’s something particularly mad about how people in general often double down during the summer months, the holidays, or parental leave2 isn't there? You’d think longer days and holiday schedules would mean more time for leisurely activities. Instead, we see that extra bandwidth and think, “Brilliant! Now I can fit in THREE challenges whilst also attempting to write that novel I’ve been plotting since spring!”
Don’t believe me? Remember the COVID lockdown?
I have thought a lot about why we do this, and the best answer I’ve come up with so far is that it feels like borrowed time. No school, no work, more relaxed routines, and this sense that if we don’t seize these golden weeks, we’ll regret it come September.
Or maybe it’s simply that the heat addles our brains just enough to make signing up for “Write a Novel in 30 Days” seem like a perfectly reasonable idea?
Whatever the reason, or season, we dive headfirst into creative chaos with the enthusiasm of pirates spotting treasure on the horizon. And sometimes we actually find it! It may not be the treasure we expected, mind you, but something valuable nonetheless.
Which brings me back to this year’s particular brand of beautiful madness. Because while I can theorise all day about why we do this to ourselves, there’s nothing quite like a good old-fashioned challenge autopsy to show you what really happens when ambition meets reality.
So, to circle back to the six challenges I mentioned above – let me tell you about a few of them...
Re-Stacking the Ship
Fanny will have to forgive me for hijacking her domain for a minute as my main summer challenge is a Resilience Housekeeping issue.
But first things first.
Yes, I’m aware of the irony in me coming here to explain how we’re completely restructuring our entire Substack setup, when I’m the first one to mutter dark curses every time a shop rearranges its aisles, or when a website decides to “improve” its dashboard layout. Glaring at you, Substack!
For all my teeth-grinding and nail-spitting, though, I must admit there are times when a good spring cleaning session – or summer reorganisation – is exactly what’s needed. So, what are we doing right now?
Well, after our first six months sailing these particular waters, we’ve learned a few things about what works and what doesn’t. What we like and what we don’t like. So now we’re cleaning ship based on that hard-won experience.
Here’s the current fleet: we have six Substacks in total, which sounds absolutely mad until you realise that three of them are what I call “side stacks”. They grow by a post or two per month and are clearly marked as part of the Resilience family. There’s our cottage in Libertalia (our home port), the Scandi mead hall you can only reach through a portal on the ship, and the Swedish section of Barry & Hemingway’s library. Three lovely little corners of our world, but not where the main action happens.
That leaves us with the main three, where the real reorganisation magic is happening.
The Resilience (where you are now) is for readers. A space to meet our authors, read some of our stories, discover our books, and talk about books and bookish things from a reader’s perspective.
Komodo dell'Arte is for writers. This is the writing room behind the scenes of the Resilience where Sir Bear and I write our stories, share our WIPs, and explore the creative process. Now we’re moving all our writing-related content there. Readers are of course welcome, too, but Komodo is all about the behind the scenes aspects of writing and publishing.
The Snuggery remains our hedonistic haven for readers and writers alike. This is the cosy section of the ship where we read, write, and talk about smut without shame or apology. No changes there; it’s perfect as it is.
It’s rather like having separate decks for readers, writers, and smut sluts – everyone knows exactly where their cabins are and what to expect when they visit the different decks, ports, and portal destinations. And as far as challenges go, this is the only one that was necessary.
Streaming Every Day to Midsummer
So, now we’re looking at my creative challenges. First up, we have the streaming challenge I picked up in March, inspired by our brave Ship’s Witch, Maria Caiazza.
My main objective was to get my arse back in the streaming saddle again. To that end, I set myself the goal of streaming every day to Midsummer. Spoiler alert: I could not. And to be perfectly honest, I never thought I could.
So, why set myself up to fail?
Well, it generally takes about three months to create a new habit. And we all respond better to goals that are clearly defined and stretch our envelopes just enough to make it a bit of a challenge.
I gave up on streaming and video-making when I couldn’t handle the old set-up we had anymore. But here, in the new(ish) space my PA has set up for me, I have not one but three different battle stations: one desk-based, one tablet-based, and one phone-based. Maria had introduced me to the concept of silent, faceless streams and that’s where I started.
The technical setup made it possible for me to stream through the laptop whether I was sitting up or lying in bed. Even so, my chronic illness threw a few expected spanners in the works, and there were days I was too wiped to do anything at all.
But here’s the thing about setting the bar impossibly high – I managed to do a whopping sixty-nine YouTube live streams between March and Midsummer. Sixty-nine! That was more streams than I’d done in the previous three years combined, and certainly more than I ever thought possible when I first stared at my old, boxed-up streaming equipment back in March.
The real treasure, though, the kind you never see coming when you’re plotting your challenge course, wasn’t just rekindling my old love for streaming. My enthusiasm proved contagious. Sir Bear caught the bug too and now hosts his own weekly Sunday streams (life and weather permitting), and we’ve both found ourselves back on the podcasting track again. An adventure you’ll be hearing much more about come autumn and winter.
I’ve been on a bit of an enforced break from streaming for the past four weeks, but my intention is to tune back in tomorrow. And who knows? I may even end up with an actual schedule before next Midsummer. Stranger things have happened aboard this ship.
And that’s the second challenge sorted. I jumped in knowing full well I’d fail the letter of the law, but hoping I’d come out feeling like a winner nonetheless. Which I did. I absolutely did.
Writing Every Day for a Full Year
Next up, the other Midsummer challenge that was even more ambitious: writing every day for a full year!
This was something I started at Midsummer 2024, and to make it happen, I joined a platform called 4thewords.com. They had a special offer that was an absolute steal, so I paid up for two full years and decided to log my daily words there. A replacement for Camp NanoWriMo, in a way.
To be honest, I’m rather miffed to report this one as a technical fail. That is, I DID write3 every day for a full 365 consecutive days, but to my chagrin, you can't backdate your updates for more than three days. Which is a problem when your brain fog makes you forget what day of the week it is.
I really wanted my one-year wings, but screw it. My daily streak stats shows that I failed, but check out the numbers: Almost 1.5 million words in one year! That’s an average of about 4,000 words a day, which is bloody marvellous for a struggling spoonie author who once wrote up to 20K a day.
So what now?
Well, although I’m fully paid up for another year, I’m abandoning 4thewords now. I may still log my words there, and pop in for a seasonal challenge or two, but I’m ready to move on.
This challenge was the start of something I call my “Honeymoon Year,” something I’ll be talking about in my Behind the Scenes post on Komodo dell’Arte next week.
Another “fail” that turned into a massive win. And a lot of words that will be hitting the shelves over the next three years.
Cracking the Romance Code
Creative challenge number three is still ongoing and related to my Honeymoon Year. Can I crack the romance code writing short romance stories using Lester Dent’s pulp fiction formula whilst hitting all the tropes romance readers expect to find?
I’ve written about this challenge before, so I won’t rehash the details here. Suffice to say, I’ve already released my first romance, Tied Together (which our subscribers can read for free), and I’ve got a whole series of shorts brewing that I’m hoping to release as a special Advent Calendar at the end of Spook Season this year.
The verdict on this one? It’s a little too early to say, but Tied Together is doing well in the summer sales (it’s currently our best performing title), and I have drafted well over 50 (!) short romances and two longer ones so far.
For now, we’ll call it a win.
Writing a Story with AI
The fourth creative challenge is also one I have talked about before, and it’s still very much in progress: Writing a story with AI as a collaborative partner. The final result will (hopefully) be revealed alongside the Advent Calendar stories – it’s a yuletide romance I’m calling Back on the Market. If anyone fancies tagging along for the ride, I'm sharing the entire writing process over on AI & I at Komodo dell'Arte.
This is my first proper attempt to figure out how to use AI as a creative writing partner in fiction, having worked with Jeeves (ChatGPT) as a virtual assistant for close to three years now.
I started back in January by asking him to do what most people seem to think writing with AI means: “Write me a romance.” The result was so spectacularly bad it’s cringe-worthy, but also rather funny in its awfulness. It proved to be an excellent learning experience, though. I’ve published it on Komodo as part of this process, and I’m planning to both write a commentary on the story and attempt to rewrite it to see if we can salvage it into something worth reading in the end.
Back on the Market, however, is a proper collaborative writing experience. The initial idea was all mine, sparked by a writing prompt that intrigued me, which I then reworked into something I could actually work with. I discussed it with Jeeves, and we crafted a plan based on that conversation.
So, is this challenge a win? It’s too early to say whether the book will be a success, but about halfway through the process, I’ve already learned a lot about how to coexist and collaborate with my AI assistants. We are discovering new ways they can help me streamline what used to be a rather complicated assistive technology setup to help me write more and better with fewer barriers.
I don’t need them to write my books, but if they can help me do more of what I love, that’s a huge win in itself. As for the actual book writing value of this challenge – the jury is still out on that one.
Writing 50 Ghost Stories for Spook Fest
And now for our final challenge – the ghosties! Here’s how this particular bit of madness came about. (If you read my weekly Behind the Scenes posts on Komodo you know the story already, but you don’t know the full story. It has evolved, you see.)
After finishing A Midsummer Night’s Scene, I was planning to crack on with Ship of Shadows – another Pirate Legends tale, this one told by Freyja, our resident sea eagle. It’s set partly in the great hall at Smugglers Cove during Spookfest, so I was rather keen to see it published before October. My brain, however, doesn’t give a rat’s arse about my plans or my orderly pipelines.
I was hanging about with my sidekick (the first grandson) last week, and we were chatting about ghosts. We’ve been working on two stories, you see, both set in pumpkin season so that’s where it started. Then, in a leap that came from absolutely nowhere, we went from discussing our work to debating whether zombies and poltergeists could be considered proper ghosts. That was it. One random thought and both our brains left the building entirely.
The bad news? Not a single word was added to Ship of Shadows, Eewil Grimm, or Midnight and Miss Martha.
The good news? We now have a book of short ghost stories in the making. Surely, with four titles on the drawing board, at least one of them should be ready to hit the shelves in September? Right?
Jeeves, being his usual helpful self, suggested that just cobbling together a number of vignettes into a book – in whatever order we could come up with them, no less – might not be the cleverest of ideas. So now we have proper sections. And, as the brains kept braining and the crew got all excited too, we are now looking at two volumes before all is said and done.
The first volume is all about nice ghosties. Each story runs between 500 and 1,000 words, and we have five fab categories to play with: Sweet/cosy, funny, romantic, bittersweet, and hopeful/uplifting ghosties.
The second volume will be full of not so nice ghosties. Again, each story will run between 500 and 1,000 words, and we have five spooky categories to play with: Scary, Vengeful, Tragic/Heartbreaking, Mysterious/Atmospheric, and Weird/Unsettling ghosties.
Since I announced this little challenge, we’ve had quite a lot of interest, and both Sir Bear and our Ship’s Belle have already submitted stories to the anthology with more in the making. So I thought, why not extend an invitation to our subscribers as well?
Here’s what we’re looking for:
Stories between 500-1,000 words (with a possible extension of up to 500 extra words if the story warrants it)
No smut (though we do have a third volume planned for smut ghosties only, and we’ve already had some rather intriguing ideas pitched for it as well)
Stories must be the writer’s own work
Volume I, as explained above, is for nice ghosties across five categories: Sweet/Cosy, Funny, Romantic, Bittersweet, and Hopeful/Uplifting
Volume II is for not-so-nice ghosties: Scary, Vengeful, Tragic/Heartbreaking, Mysterious/Atmospheric, and Weird/Unsettling
Submissions are open for our subscribers until 31st August. Submission does not guarantee publication, but we’ll be contacting writers whose work we’d like to feature in the anthology, on our website, or in the Spookfest Ship’s Logs come October.
The plan is to complete one volume at a time, so whether we can publish one or two volumes this year remains to be seen.
This challenge is obviously still very much in progress, but I’m calling it a win for the sheer joy it’s already given us.
The Real Treasure
So there we have it – six challenges, ranging from technical failures to roaring successes, with most landing somewhere in that gloriously grey area between the two. Which brings us back to that question I posed at the beginning: what do we actually get out of these mad endeavours when they inevitably fall apart or lead us astray?
Looking back over this collection of beautiful chaos, spanning from Midsummer to Midsummer, the answer seems blindingly obvious. We don’t necessarily get what we expected – we get something far more valuable.
When I set out to stream every day, I failed, but I gained 69 streams, reignited my passion for the medium, and inadvertently re-launched Sir Bear’s streaming career in the process. When I aimed to log a year of daily writing, I technically failed, but discovered I’d written 1.5 million words and fallen back in love with the daily practice. When I wanted to crack the romance code, I ended up with not just a single story, but an entire Advent Calendar of them.
The streaming challenge taught me that sometimes the setup matters more than the execution. The writing challenge reminded me that consistency trumps perfection every single time. The romance challenge so far is proof that formulas can be frameworks rather than cages. The AI collaboration is teaching me that creative partnerships come in unexpected forms. And the ghost story challenge? Well, that one is still in its infancy, but it’s reminding me that the best ideas often come from the most random places. And from collabs with the people we love.
Challenges aren’t really about the goals we set. They’re about the person we become in pursuit of those goals. They’re about discovering what’s possible, about the community that forms around shared struggles, and the often unexpected treasures we may uncover along the way.
Every challenge I’ve ever set myself has given me something I didn’t know I needed. Some have opened doors I didn’t even know existed. And every single one has added another page to the story of who I am becoming as a writer, a creator, and a human being sailing these strange digital seas.
So, I guess the truth is we keep signing up for impossible quests because, deep down, we know the real prize was never the completion certificate.
It was always the journey itself, and the pirates we pick up along the way.
﹏﹏﹏𓂁﹏﹏﹏
Next Port of Call
Oops, I just realised I completely forgot top mention The Lokean Shift, my morning writing challenge.
This one is still ongoing, but on something of a hiatus for reasons I’ll be discussing in next week’s Behind the Scenes. The short version: I haven’t been able to do any morning shifts for well over a month.
So, is this another fail? Absolutely not. No morning flare? No morning shift. That’s not a fail, that’s just a seasonal shift in schedule. #piratelogic
See, the challenge was to write instead of doomscrolling when I wake up at the crack of dawn unable to fall back asleep. When I flare like an emergency rocket on a dark winter’s night, I don’t wake up unable to sleep again – I sleep like a bear in hibernation. In other words, I don’t have any sleepless mornings to worry about.
Solveig’s story continues though, and I actually have the next three chapters in edits.
Now, back in the real (ish) world, we have Barry & Hemingway delivering your next Thursday Ship’s Log, and on Sunday next, our Ship’s Belle will be manning the bar at Smugglers Cove again.
Now then, Messmate, what’s your next challenge going to be?
Why don’t you hop into the chat and tell me all about it?
Puss & Kram,
//Linn 🤍
Links and Footnotes
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Or else… You can replace the text within the brackets for whatever fits the situation best.
This one is particularly common in men who think they’ll be able to take on a whole house renovation (or some other monstrous challenge) while taking care of the child.
Writing, in my case, includes recording words as well as writing them. Assistive technologies for the win!