Steph Lessing Paint Nite artist

Featured Artist: Meet Stephanie Lessing

This is Stephanie Lessing.

Steph Lessing Paint Nite artist

Stephanie is an artist for Paint Nite Boston and she also works at Paint Nite HQ in the marketing department. She is the queen of spreadsheets, one of the most organized people we know, and is impressive with a paintbrush. She’s also the hands (and talent) in our Featured Painting videos, like this one for May.

Paint Nite Featured Painting – Nesting Home


We’re big believers that anyone can pick up a paintbrush and create something special. That’s why we love Paint Nite. But what makes someone go from holding a paintbrush to wanting to stand in front of a crowd and bring a painting to life for all to see?

So we thought we’d take you behind-the-scenes to find out what makes a Paint Nite artist tick. How do you become a Paint Nite artist? Why?

The Story Behind a Paint Nite Artist

Steph says: “When I was 10 years old, I dreamed of going to art school. I came from a line of artists, so creativity was always a part of my childhood.

But something changed along the way and I went from doodling, sketching, and painting to Excel spreadsheets and econometric modeling. After a while, I found the need to rebalance my analytical career with my creative intuition.”

“I attended my first Paint Nite event a few days after being hired for a marketing position here. I decided to take my mom with me. She had gone to art school and actively paints in retirement.

Paint Nite Artist Stephanie Lessing and her Mom

I hadn’t painted since I was 13 and the feeling of a paintbrush in my hand as an adult was strange and intimidating. I felt a bit panicked. I wondered whether or not I was even creative anymore. Two hours later, I sat back in my chair, staring at my painting in complete astonishment.

It took about a year and four Paint Nite events for me to realize that creativity is not a ‘use it or lose it’ skill. It can sit dormant within you for years just waiting for an outlet to surprise you.

I became a Paint Nite artist because of that feeling of accomplishment and satisfaction when you realize that you can make something beautiful with your hands.

My favorite thing about hosting Paint Nite events is hearing people tell me that they’re nervous about their artistic ability. As the night progresses, I watch their paintings come alive and I see pride in their eyes when they realize that they can do it.

Even better is when the adventurers of the group try new techniques or interesting spinoffs from the original painting. It’s truly amazing what ‘uncreative’ people can actually do.

Paint Nite Flower Monster

“For me, being a Paint Nite artist is not just about showing people how to unleash their creativity and to experiment with a new medium—it’s also a personal growth journey.

I am terrified of public speaking and I decided the only way to overcome it was to force myself to do it as often as possible. I learned to use the excitement of the audience to fuel my own energy and become comfortable talking to and joking with anyone. That’s not to say I don’t still get nervous once in a while, but hosting events pulled the extrovert out of me that had been hiding for years and has increased my confidence in many areas of my life.

Being a Paint Nite artist isn’t a side hustle; it’s a part of my week that keeps me engaged, excited, creative, and social.”

You can do it! Come paint with us and find out more about joining the Paint Nite platform. We’d love to have you on the team.

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One Comment

  • Tammy says:

    i applied to be a paint nite host online 12 times… starting last september and never got an answer
    I love this idea and I feel the same way as this paint nite host .
    i did start my own company doing this and will never go back to a regular mindless job this one is so fulfilling
    I almost want to say thanks for not hiring me, it would have been great to be part of the team but this forced me to put myself out there

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