face the dragon🀄️

Photo by Benjamin Wedemeyer on Unsplash.

In 2001, I lost a dance battle in primary school to the tune of Sisqo’s Unleash the Dragon. My opponent (enemy) performed a few more knee slides than I could muster. Young Tobias watched victory slip away from his grip as the timer wound down: four, three, two, one….and I was relegated to second place.

Disaster.

In a Nigerian household, second place is tantamount to failure. The standard retort is “the person who came first…do they have two heads?”. There are no participation trophies. No orange slices for “getting out there” or “putting it all on the field”. Winners and losers from day one. Thankfully, my parents weren’t this extreme and they didn’t care about dance. So I didn’t have to scrub the shame off my body.

I’m still slightly miffed because those winning splits were completely off-beat. Sis kept diving to the ground knee-first without any regard to the music. In fairness, I probably wasn’t any better. My shoulders didn’t find rhythm until boarding school. Something about the utter madness of daily life in those dorms injects melody into your bones. You will dance so you don’t cry.

Twenty years later, I found myself facing another dragon—a metaphorical one, of course. Since I reincarnated as a writer last November, I’ve churned out essays on a consistent schedule. I found my groove. My digital garden is splattered with messy notes across Google Docs, Substack and my inbox. I hit peak writer in Seville—instead of dancing to Titi me Preguntó in a club, I opened the Notes app to jot down an essay idea before it floated away forever.

So where’s the dragon?

Well, I always wanted to turn on paid subscriptions at some point. I wasn’t sure when or how to do so. Instead of simply trying it out, I inadvertently constructed this towering beast I couldn’t defeat. The questions and worries rained down on me:

Would accepting money turn this into a job…that I’d eventually hate?

Did I need to reach 1000 subscribers first?

Should I focus on what value-add my paid subs would get? An extra essay? A community of the sabbatical-curious? Informal office hours? Video posts?

April was a big month here. Nearly a hundred of you subscribed. And a lot of you joined after reading my Every essay so that brought up the usual creator dilemma. Do I niche-down and write more sabbatical-focused stuff for those people? Give them actionable, practical advice? Or do I continue to follow my curiosity and energy?

My mind loves to drift and wander so in truth, I knew it would be really unnatural to hyper-focus and I’d eventually get bored or burned out. See how I connected my primary school dance competition to my worries about building a writing business? I need that lightness and wide berth, it’s one of my writer strengths. It’s also why I’m a tricky teammate in Codenames (cuz my brain does backflips when it should be doing a cartwheel🙈). Anyway, I didn’t want to narrow my scope but the questions continued to bother me.

I grabbed my forceps and began to dissect them from every angle. Oh I could run this elaborate experiment to test all the options. I could design these little variants to see what readers want to see. I could trial a light coaching business, a sabbatical mini-series, notes from my travels, a paid discord community, a this, a that. Then paralysis set in. I analyzed myself into an inescapable ditch.

This pattern is quite common in life. We have these hunches or little snippets of ideas that are full of promise. But we end up sabotaging them by drowning them in questions. Your inner engineer or consultant goes into overdrive. You feel a need to “productize” and optimize the thing before it’s even alive. Every seam must be perfectly sewed, every crease ironed out and every loose thread cut off.

I know the feeling. My ego wants every new essay to be my best work. Every sentence perfectly manicured and pruned at the edges. It’s been there my whole life. Friend and foe. But if I spend forever re-reading every sentence, I’d never publish anything.

Same thing goes for those dragons I constructed. I could stew in the simulations I built in my mind: Would it be better to wait till 1000 subs or should I start now? I’m halfway there, but what’s to be gained by waiting? It’s an arbitrary number in this unpredictable game we writers play.

I’ve started to reframe things in a different light. I wanted to turn on paid subs. Ok cool, that’s a hunch. A baby idea. Hunches are precious, endangered species. You need to protect them from yourself. They’re tiny, amorphous and not fully-formed. They can’t breathe on their own. Don’t drown them in your worries and anxieties. Your job is to tend, nurture and shelter. Hide them from your “practical brain” at all costs. The time will come when they’re ready to leave the nest.

This advice is as much for me as for anybody else. I’ve been trying to preach “action over analysis” to myself for a while now. But my primitive biology gets in the way. Anyway, last week I turned on paid subs and was pleasantly surprised. A bunch of you decided to support this nomadic writer. Without any additional perks🥹. I received the most genuine, heartfelt messages from readers in my survey. I couldn’t have seen any of this in my simulations.

The best thing about many hunches is that they’re reversible. Or at least they can be edited down the line. You dip toes in the water, see how it feels and decide whether it’s worth the plunge. I went nomadic, but I could move somewhere. I quit my job but I could find another one or some part-time work. I turned on paid subs for earnest supporters, but I could offer paid-specific perks in the future.

It’s human nature to be anxious and to overthink things. That squishy, glucose-hungry thing in your skull loves to spend cycles protecting you from things….even when they’re not real. Creating dragons you need to slay. Simulating futures you can’t predict. But I’m finding it’s better to act, then review, than endlessly analyze. Saves you from the mental headache. And the dragon is hardly ever as fearsome as you imagine.

I have a hunch that I should stop here. Mmm but maybe I need another paragraph. A few more words to really drive home my point. Or I could toss this word salad with a lighter dressing. I’ll listen to the hunch.

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🌸One more thing🌸

Writers, I’m building an app to help you. If you’re like me, you enjoy writing long-form essays but absolutely detest writing tweets, FB posts or LinkedIn posts to promote your work. So I’m building Essence, an AI-powered app to ease that burden.

It’s very early and I’d love some more feedback. Give it a whirl, try it out and let me know what you think in the comments or here.

PS - if you enjoyed this piece, please let me know by liking the heart button. Muchas gracias!