How a Cruel Art Teacher Sparked My Creative Breakthrough

Sometimes the people who doubt us are the ones who send us straight into our power.

Another sunny day at the Greek villa in Katastari, Zakynthos

This is the final installment of a three-part series on what it means to be stuck and how to unstick yourself. If you missed the previous two weeks, click here and here to catch up. If you enjoyed reading, I’d love a ❤️ or to see your words in the comments.

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What happens when you stop waiting for permission and start saying yes to what makes you feel alive?

The moment I started saying yes to myself, everything began to change.

Sometimes, the yes was clumsy, a bit scary, and occasionally involved glitter.

After years of not knowing what I wanted, I began saying yes to the tiniest sparks of curiosity.

I signed up for a Spanish class. I learned how to line dance. I raised monarch butterflies. I played pickleball every week, even though I wasn't sure how to hold the paddle right.

These weren't grand reinventions. They were quiet ways of listening for my voice again.

But the most daunting "yes" was art.

I had a lot of mental baggage about painting, especially when it came to something as intimidating as a blank white canvas, so I tackled it first. I signed up for a beginner's watercolor class at a studio I'd visited once for a Sip and Paint. I didn't think I had talent, but I wanted to try.

On the first day, the teacher demonstrated how to hold our brushes and mix colors. I chose to paint a photo of a beach, with dune grasses swaying in the foreground and the ocean and sky in the background. I wanted it to feel soft and simple.

"It's WATERcolor," my teacher said in the first class, "don't use too much paint!"

But when I tried to paint the grass, it came out gloppy. My brush sometimes soaked up too much water and at other times, too much paint.

The colors weren't blending the way hers did. It looked less like coastal serenity and more like a seaweed crime scene.

In the second class, the teacher walked over to my painting, studied it, and said loud enough for the whole class to hear:

"That is not good."

She followed it up with, "I'm an honest teacher. I will never lie to you."

My cheeks burned. My brush froze. I looked around, wondering if anyone else felt the sting of her words.

What complete and utter bullshit.

A younger version of me would have swallowed her judgment whole. I had learned to stay quiet, to be good, not to make waves. But something in me cracked open.

A fire got lit.

Through gritted teeth, I said:

"If it's not good, teach me what I'm doing wrong. I'm new to watercolor painting."

She blinked, stunned, as if I’d just questioned her watercolor royalty. I half expected to be exiled from the kingdom of damp paper and muted hues.

Yet that was the moment I finally came home.

Her criticism wouldn't be the end of my creative self. It would be the beginning.

"If you hear a voice within you say, 'You cannot paint,' then by all means paint, and that voice will be silenced."

Vincent van Gogh

Let Yourself Begin Again

After that, I decided to start even more simply. If watercolor was too challenging, maybe I needed to learn how to draw first. I found a drawing teacher who was warm, encouraging, and very hands-on. Under her guidance, I progressed more quickly than I had imagined.

The right teacher doesn't just show you technique; they help you believe you're worth teaching.

From there, I discovered an art therapy studio with intuitive painting classes. No technique, no critique — just expression.

Sometimes, I painted with glitter, which felt outrageous and self-indulgent.

Some days, I used big, bold strokes.

For a while, all that came out were flowers. I didn't plan them. They just kept blooming on the canvas. At first, I resisted them. I wanted to paint something edgy, abstract, maybe a bold feminist statement.

My canvas said, “How about tulips again?” Apparently, my inner self is a gardener with feelings.

It was a totally new way of listening to myself.

A Dream I Didn't Know I Had

Around the same time, my husband and I were traveling often, especially to Greece. My husband is Greek, fluent in the language, steeped in the culture, and completely revolted by olives. (We don’t talk about it in Greece. It’s too controversial.)

We had family on two different islands. They were hospitable and welcomed us into their homes, fed us with love, and folded us into conversations that needed no translation.

I fell in love with Greece — the food, the people, and the slow pace.

Back home, friends would say, "I've always wanted to go to Greece."

And something began to stir.

In an earlier chapter of life, I had planned women's retreats — daylong, faith-based gatherings. I wasn't religious anymore, but I still believed in the power of women coming together. What if I brought a small group to Greece? What if I offered space to rest, create, and reconnect?

Would anyone come?

In June 2024, eleven women joined me on the island of Zakynthos. We swam in the sea, ate fresh meals prepared by our private chef, shared stories, and recharged our creative juices to find joy again.

No one wanted to leave. But when they did, they were changed.

So was I.

For the first time in a long time, I wasn't just the planner or the caregiver.

I was the dreamer who had made something real.

What Comes Next

And the dream is still unfolding.

This September, I'm returning to Greece — this time with Jennifer Santa Maria, an incredible art coach who believes, like I do, that creativity is a way back to yourself. (You can learn more about Jen here.)

Together, we'll be guiding a small group of women on a retreat designed to reignite joy, connection, and creative expression.

There will be art, of course — but also gentle yoga, swimming, laughing, wandering, resting, and remembering what it means to feel fully alive.

If you’re craving something more but can’t put your finger on what it is, don’t worry — we’ll have colored pencils, paintbrushes, and feta cheese. Something will speak to you.

There are still two spots left.

If something in you sparks when you imagine it, maybe that's your next "yes."

What have you said yes to this year?

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To read more in-depth about the retreat, I write in great detail about what to expect over on my Traveling Women’s Circle substack.

If you’re a big picture person, visit www.travelingwomenscircle.com to get the dates, itinerary, see the villa, and get pricing.

Are you saying yes? Hit reply and let’s talk.