How I got started as a live portrait artist
I’ve been illustrating for clients for years. When the pandemic started, I began to get an influx of freelance requests from people who wanted to work on passion projects, namely self published children’s books. I found freelance jobs through Upwork and a little bit through word of mouth. I did illustrations for companies as well, but mainly individuals.
The first two pages of Harry’s Hair by Johnny Palmer and illustrated by me.
I loved doing traditional illustration the most, and specialized in watercolor. I enjoyed freelancing, but it dropped off pretty fast after a year or two, and I quickly realized it’s a struggle to find consistent work applying through those kinds of websites (Upwork, Freelancer, and the like). The market is oversaturated but the work is undervalued. People post jobs expecting you to illustrate an entire book (something that takes many hours over many weeks or months) for just a few hundred dollars, often therefore estimating your hourly rate to be under the federal minimum wage, which, of course, is egregious.
I didn’t really know live event art was much of a thing (besides caricature work at fairs and markets) until about a year ago. In February 2025 I was swiping on BumbleBFF and I met someone who was looking for a live guest artist for her upcoming wedding. She liked my work on Instagram, and asked if I’d be willing to try it.
I figured why not? I thought it could be a good match for my skills. I practiced at home by setting a timer and drawing stock photos of people posing for a camera in ways I thought they’d be sitting for a portrait. When I did a trial for her and her fiance, she loved it and hired me!
The lovely couple of my first wedding.
After the success of the wedding, my mom and girlfriend encouraged me to try scoping out other places I could draw live in order to not only make some money, but advertise the service of doing it at events and weddings.
My first choice was the Beaverton farmers market- they don’t allow craft vendors, and you can’t busk, so I got a Beaverton business license for the year, and a special events permit (which are free of charge) for various dates to be able to do live portraits right outside the market.
Then I discovered you could busk at the PSU Portland farmers market and got a busking pass. It was a hit, and my first time drawing there I made over $300. The Beaverton market, however… not so much. The foot traffic just wasn’t worth the effort if I couldn’t be directly inside the market.
When I drew at the farmers markets, I would advertise that I work events and weddings, and I ended up getting my second wedding client that way!
Last year working at the PSU Portland farmers market.
This year I started networking, getting into the wedding industry more, attending PDXperts events which have genuinely been invaluable for making connections, and working on my new website. Through all of that I’ve already increased my client acquisition exponentially.
My outfit for my first PDXperts event vs the fashionable rendition by fellow live artist Bowtie and Brush!
Figuring out SEO in particular has been a struggle and a little demoralizing at times, but overall it’s been such an exciting learning experience.
I’m so glad I found this little niche, and I hope to continue to work at it and improve my live art skills!
A drawing from a baby shower I worked in May 2026.
