Why I Started Painting — Even Though I Knew I’d Be Bad at It
Creative work doesn’t need to be good, marketable, or impressive to be worth doing.
I’ve never waited for anyone’s permission to do something. If anything, I’m known for doing the thing people warn me not to do.
But when it came to painting, the voice holding me back wasn’t someone else’s — it was my own.
You’re not good at this.
You’ve never been trained.
You can’t even draw.
It took me forever to realize: none of that matters.
You don’t need to be good at something for it to be worth doing.
That belief came from a deeper realization: something in me had gone quiet.
A part of me — physical, playful, imprecise — has been silent lately. And that silence made me ask: what’s missing? What is the thing I do that is just for me? The thing that fuels me, but isn’t about work or output?
That’s when I realized I didn’t have a third place. Not anymore, at least.
A place that isn’t home, isn’t work. But somewhere else I go — or something I do — just for myself. For my inner child, even.
Throughout most of my adult life, that place has been a class that I’ve elected to take.
I love to learn. Not just for the sake of knowing but to understand things from the inside out — to try them, test them, and be able to say, “I’ve done that.”
If I’m going to have an opinion or a vision, I want to know what it actually takes to bring it to life.
Dance classes used to be my third place. I could go for an hour, struggle through learning a routine, and leave. Dancing is such an all-encompassing activity that your brain doesn’t have space for anything else in that hour. It was an active meditative practice for me. And whether I nailed the routine or completely botched it, I still showed up and had fun.
Tell me I didn’t eat that choreo up!
I’ve done much scarier things with much more at stake — and I did them without hesitation.
I’ll launch a business without blinking — but I won’t let myself buy paint without a fucking certificate. That’s not funny. That’s fear dressed up as logic.
What’s wild is that I didn’t always think like this.
When I was a hair colorist, I worked at high-end salons in Atlanta, New York, and London — all without a cosmetology license. I was professionally painting hair.
Colleagues would ask why I didn’t just go get certified. I would look at them and say, “My books are full. I don’t need a piece of paper to tell me I’m an artist.”
I believed that then. So why not now?
Maybe because as a hairstylist, the value in your work lies in what your client thinks about it. There were times I hated a full head of highlights that I did, but my client felt like Jennifer Anniston on the red carpet. Maybe the weight of other’s people’s perception of the outcome became so ingrained in me, that I applied that to all of my creative endeavors.
Outside of grade school art class, I’ve never really tried to paint. In the moments where I made the attempt, I realized very quickly that I did not have a natural talent for it, and that is very demotivating. I’m actually quite embarrassed to share any drawings or paintings that I’ve made because all I keep hearing in my mind is, that sucks!
My inner sabbatour needs a fucking muzzle.
In the meantime, I’ve been trying to find a new version of that third place — something physical, unpolished, just for me. But I kept hesitating. Nothing quite stuck. Until it clicked.
Last spring, I didn’t expect to find myself moved when I was a +1 at some stuffy art show. But then I saw something intriguing: a handwritten note encased in glass that stopped me in my tracks.
“I want to paint, but I don’t know how. So instead, I’ll write about it.” — Mary Henry
It felt like someone had torn a page straight from my journal. Because painting is the creative urge I’ve been wanting to scratch. But my type-A personality has stood in the way.
When I think about what’s underneath my urge to paint, it’s less about the result and more about the action. I just want to do it. I want to physically do it. Something in my body is telling me it will be therapeutic — and I feel like I need to listen.
Maybe it’s an impulse leftover from my hair coloring days. It just changed forms.
As I’ve been exploring softness, I keep coming back to a few reminders:
🎨 Art is subjective.
🎨 Art is personal.
🎨 Art does not have to be “good” to be worth making.
🎨 Art is about process, not perfection.
So, I’ve decided to challenge myself: I’m going to make some fucking art — and define what softness looks like for me in the process. It looks like not just creating something, but actively choosing to be happy with it. Not because it’s good or bad — but because it’s done!
As luck would have it, I live near a huge Blick Arts store that had the most amazing sale going on recently. I gave myself a budget of $100 and went shopping like an excited grandma at a Macy’s one-day sale. The floor associate could tell this was my first rodeo and helped me get everything I needed. I left with a bag full of goodies — only $20 over budget. Not bad!
Then came the next hurdle: I got home, unpacked everything, and thought… What the hell am I supposed to paint?
That’s when I had a lightbulb moment.
💡 I often struggle with finding imagery for my Substack. I’ve had fun using AI-generated images, but have still found them a bit impersonal. So I have decided to explore finishing an essay and then painting whatever comes up for me. The finished product will be the hero image for that post.
Now I get to share two creative outlets with people at once.
Here’s how I’ll do it:
✅ Put my phone on Do Not Disturb.
✅ Turn on some classical music.
✅ Set a timer for 45 minutes.
✅ Create something.
No pressure. No expectations. Just paint.
My intention is not to make these paintings to possess — I’m making them for the experience. For the therapeutic effect that accompanies putting brush to canvas.
I don’t want to keep them and I don’t want to throw them away, so each piece will be listed in the shop on my website. Not because they’re masterpieces, but because the creative act behind them has value.
Maybe one of these pieces could be a reminder of that in whatever your own practice is. Or maybe, if an essay I write resonates with you, the accompanying art can help keep it alive.
As a bonus, if you purchase one, I’ll gift you a one-year subscription to my Diary — the highest subscription level of this Substack.
I’d love to hear from you.
Is there something you’ve quietly wanted to try — but haven’t let yourself, because you’re afraid you’ll be bad at it?
What would approaching it with softness look like for you?