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👻 Boo & the Writing Demons

Michael Dean
Michael Dean
5 min read

I've been writing online for around a year now. There are all sorts of tips and tactics I've acquired, but none of them matter if you don't muster up the courage to face some root-level fears. Don't let some un-wrestled demons sabotage your dreams. I almost did.

Writer's block, imposter syndrome, and busy-ness are just a few of the many culprits. There's a whole palette of emotional blocks that prevent writers from starting or finishing. It helps to characterize these emotions:

The instant gratification monkey.
The devil on your shoulder.
The final boss to slay.
They're big, they're bad, they're evil.

These characters are more than "excuses" though. Sure, they're imaginary, but they're persistent with real effects. They're writing demons with the capacity to haunt. The most important thing we can do is find them and slay them, otherwise our tactics are worth squat.

The worst part?
These writing demons can be invisible.
(This is why I call them demons.)

Our writing demons behave a lot like "Boo," the ghost from the Mario franchise. From their 2D-origins on Super Nintendo, to the 3D-versions that followed Mario 64, all Boos behaves the same. Check out what happens below:

There's a courtyard full of Boos lurking in the background. But as soon as Mario approaches one, the little bastard turns transparent and shrinks. It's a demon that hides itself when attention is drawn to it. Boo does this is in all versions of Mario. When you look at the ghost directly, it seems like nothing is there, but as soon as you turn around, it materializes and brings out its fangs.

Boo is a blind spot. "Nothing to see here!" when looking at it, but haunting our creative life when we look away.

Like Boo, the true blocks preventing us from sharing our drafts, experimenting with voice, bringing our life into our work, or covering certain topics, are difficult to see.

When we troubleshoot the problem, the root cause becomes invisible, and we're left blaming something else. Behind any excuse is a writing demon that's specific enough to give a name.
  • A complex note-taking system that prevents you from publishing? The nocturnal-librarian will endlessly categorize without writing anything them self. Solution: Only use research after you've gotten feedback on a draft.
  • Are you endlessly shifting your outline to iron out your grandiose manifesto? The whale-hunter will spend years chasing imaginary beasts that might not even exist. Solution: Scope shorter essays. Publish something you can write in a single sit down.
  • Do you feel like it would be unprofessional to curse or share details about your life? The obedient-employee always feels like their boss or their mother is watching. Solution: Write under a pseudonym.

The kicker is that all of these solutions are easy. The real challenge is admitting that you've been blind to a ghost that's followed you around for 25 years. There's a clear psychological reason why these complexes lurk within us:

The truth hurts.

Our subconscious defends us from the things we can't handle. But these emotions sabotage our most brave objectives. By naming our writing demons, we can know them and look for their footprints. It also helps to have friends who are willing to be real with you when they give you feedback.

"Hey man, looks there's a whale-hunter behind you," would've saved me years of toil.

Nothing illustrates demon-blindness more than my crisis after Write of Passage 5.

The most valuable feedback I ever got was from my friend Ritesh right after the cohort ended. He said something along the lines of:

"It sounds like you're trying to impress Marshall McLuhan with your academic mumbo jumbo, but I'd really rather see "Metaverse Mike." Does he wear a cape? Why are you afraid to bring yourself into the story?"

Was I... afraid? A good question from someone else can shine a spotlight on your writing demon. I'd never considered that I housed a fear to bring my own life into my writing. I suspected my writing was weak in the personal dimension by CHOICE, not fear. As I went through Write of Passage the first time, I must have been affirming the same excuse to myself:

"The audience wouldn't want to know about me, I'm trying to blow their mind with a vision of the future."

Like Mario looking straight at Boo, when I introspected around the personal dimension, all my fears turned invisible. I only saw wonderful and rose-colored paintings of the Metaverse. I needed Ritesh to tell me, in a polite and playful way:

"Dude, can't you see you're being swarmed by a gang of Boos right now?"

This feedback led to a low-grade, but necessary identity crisis. I deleted the website I built during Write of Passage, changed my name to Dean Dukelis, and spent 3 months writing Crashing Facebook Connect and similar unfinished pieces. It was a series of delirious fiction, based on real events I experienced in VR. Even though I didn't publish much, I was showing up every day, and, for the first time ever, writing from the first person point of view. Even though the whole thing felt like a failure, in hindsight, it was a phase where I focused on my weakness. I brought myself into the essay and slayed my most urgent writing demon.

Eventually, I said, "Enough of this Dean Dukelis character, it's too limiting. I'm just going to go back to Michael Dean, and publish whatever I want, without restraints." I launched a Notion site at the beginning of 2021, and have published over 100 things since. I even published random moments of my vacation that included scenes my wife and mother-in-law. There's no way I would've felt the liberty to do this if I hadn't slayed my Boo.

There's a catch though. There's more than one Boo. There's a whole army of these fucking cartoon ghosts. And you think that last demon you slayed was tough? The next one is 5x bigger.

Josh said it brilliantly in a break-out room last night.

"The bad guys always get bigger as you make it farther into a video game. If they get smaller, you're going in the wrong direction."

Everyone has more beasts to slay, and I'm starting to triangulate the next demon I want to wrestle. Even though I can nerd out on tactics, workflows, and process, it's helpful to remind myself that introspection isn't optional, especially as you get further down the path.



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