Weird Creative Habits That Actually Made Me a Better Artist
I've been making a full-time living as an artist for over a decade, earning a lovely liveable wage by combining digital product sales, coaching, content creation, and merch through my persoanl art brand, Letter Shoppe.
I'm neurodivergent, covered in ink, and chronically online, so if you're looking for unhinged but actually helpful advice on how to grow your art practice, you're in the right place.
As a creative, there are so many ways we get in our own way.
Imposter syndrome is real, which makes sense when your entire job is to talk about your feelings and then slap them onto a canvas, your iPad, or (the scariest one of all) the internet.
It’s totally normal to feel this way. Honestly, most famous artists didn’t even get popular until they were dead, so they didn’t have to worry about secondhand embarrassment or waking up to 13 notifications and a random hate comment.
Now? We get real-time feedback within 10 minutes of posting, whether we want to or not.
As someone who gets bored easily, I’ve developed a lot of weird little habits to trick myself into being my most creative and authentic self… without letting the cringe stop me. (Well, I still feel the cringe. But at least I keep making content anyway.)
Weird Habit #1: Give Your Art a Fake Personality or Backstory
This is one of my all-time favorite tricks: giving my art a full-blown backstory, even when it’s just a sassy frog with attitude.
Saucy Frog Booty T-Shirt - lettershoppe.com
Take this piece for example, Big heart. Bigger booty. Unstoppable energy. This frog isn’t just a drawing. She’s a vibe. She’s marching into your life with heels on, ready to body slam imposter syndrome and collect compliments like Pokémon.
Is she going to a drag show brunch? A bachelorette party? Court? Doesn’t matter. She’s confident, unbothered, and probably has a side hustle.
Giving my characters this kind of energy makes the art more fun to create and a thousand times easier to talk about online. For me. this method makes it easier to title pieces, write Instagram captions, and create storytelling-based posts without sounding like a robot.
Weird Habit #2: Treat Social Media Like a Sketchbook
Who decides when it’s "done" anyway? I treat social media like a sketchbook, NOT a portfolio. It hasn’t really been a portfolio platform since like, 2018.
And as an artist, you don’t need to create brand-spanking new work just to show up online. Talk about that piece from six years ago. Repost it with a new vibe. No one will notice.
Screenshot of my Buffer Sent folder
Change the background color, add a seasonal theme, and suddenly it’s new again.
Plus, no one remembers what you posted three months ago, let alone three years ago.
Change the caption. Reframe it with a new hook.
I literally use Buffer to schedule content across 11 platforms, and when I’m low on spoons, I just hit “duplicate” in my sent folder.
Weird Habit #3: Post Before It Feels Ready
Posting before you're ready stops the over-perfection spiral. You’ll start learning what resonates based on engagement, and yes, that includes your messy sketches and silly doodles. Sometimes the stuff you’re least confident in is the very thing people love the most.
Make space for those low-pressure moments. Confidence isn’t something you wait around to feel, it’s something you build by showing up again and again.
Weird Habit #4: Wear Your Own Art Everywhere
Moth to Flame: Cotton Tee - lettershoppe.com
I rarely leave the house without wearing something I made through Letter Shoppe. It makes it so easy to find my people. I’ve had strangers stop me to say they love my glasses, my shirt, or my vibe, and I swear I remember those compliments longer than any online like.
Also? I am not afraid to ask for someone’s number if they compliment my art. Wearing your work is peak confidence. It’s anti-capitalist flirting. We love to see it.
A girl told me she liked my Moth to Flame tee and now she follows my shop on IG and it sold that very day. All because I left the house wearing my own stuff. Wild.
Weird Habit #5: Make Ugly Art On Purpose
This is how I break the perfection loop. I’ll give myself 7-10 minutes to draw something with my non-dominant hand. Or I’ll look at the weird wood grain knots in my floor and turn them into cursed faces.
It doesn’t matter if it’s good if it gets me started. You don’t need to scroll Pinterest for hours. The inspiration is already inside you.
Weird Habit #6: fake your portfolio
Do you want to design tampon packaging that looks like a metal band poster? DO IT.
The best way to get client work you actually like is to fill your portfolio with personal projects that feel real. It’s not fake, it’s future you in action. Whether you want to do branding, comics, stickers, or prints, just make the thing. Trust that your unique perspective is what makes it special.
There’s no such thing as “too saturated” if your art is undeniably you.
Weird Habit #7: Stop Sacrificing Your Sanity for Pixel-Sized Perfection
Earth Day Post from my art IG - @lettershoppenation
People are viewing your art on a screen smaller than your palm, bestie. Your lovingly rendered 13-layer background? Lost in the digital void.
That’s why I keep it simple:
Limited color palettes
No full backgrounds
Characters with bold, shouty text overlays
If you want to keep a version without text for prints or products, go for it. But don’t let the purest version of your work stop you from making the shareable one.
Hate writing captions? Talk to your phone. Dictate your stream-of-consciousness thoughts like you’re leaving a voice memo for your future self in a post-apocalyptic art bunker.
Then skim it, highlight what slaps, and use that for your text overlay or post caption.
Nothing has to be deep. It just has to be you.
Weird Habit #8: Start the Day With a Doodle Ritual
Marketing will absolutely eat your day alive and ask for seconds. That’s why I trick my brain into making art first thing, even if it’s weird, lumpy, or vaguely haunted. Sometimes I only have time to sketch a loaf of bread with legs or a frog wearing Crocs. It doesn’t matter.
Shout out to my high school sketchbooks full of emo eyes with 45 eyelashes and dramatic banners that said things like “F*ck School” That wasn’t wasted time. That was VERY serious doodle training.
You know how you get all your best ideas in the shower? Same deal. Your brain is distracted by something repetitive and boring, so the creative gremlin in your head finally gets the mic. Morning doodles do that. They're your ritual. Your warm-up act.
Will it be bad? Probably. Will your hand cramp from holding a pencil for the first time in a week? Also yes. But that’s the point. It’s not supposed to be genius. It’s just supposed to start the engine. We are not trying to paint the Sistine Chapel before breakfast, we're just making sure the creativity faucet still turns on.
You don’t need to make your art business more aesthetic, you just need to make it more you.
If you’re ready to reset your entire creative practice, whether you’re just now taking things seriously or you’ve been stuck for years, check out my Artist Reset Planner. It’s 80+ pages of templates, workbooks, and big questions to help you:
Find your audience
Create sustainable revenue streams
Stop waiting for inspiration and start building momentum
