Stephanie Gaffney is a live wedding painter from New Orleans, Louisiana. I decided to talk to her about the beginnings of her painting business, whether she always wanted to become a freelance painter, the main challenges, her joys and failures and what it’s actually like to do the job that you love.

So how did it all start?

She has always liked drawing, but at first, she was using only things like pencil and charcoal. She admits she was nervous to start painting because all of the colors intimidated her. But once she started, when she was about 16, she noticed it wasn’t so hard and that she was actually pretty good at it. She sold some pieces when she was in college and on university, but when friends were telling her to do it for a living she used to answer: “Who else is going to buy it besides you?”.

On University she got a degree in graphic design and got a job for a small advertising agency, where she was designing logos, websites and even started some coding. Working at a small company she was able to watch how they did business. “Business is very simple” she says. “You are good at a thing, you offer a service or product, you find clients, you do the work, you get paid.” Before working for that small agency, she had never really had a desire of starting a business. “The inspiration to start a business came from the desire to break out and do marketing and stuff like that” Stephanie admits. During this period she was just painting on the side and combining both activities.

How did she actually become a freelance painter?

“I really just quit my job and I was like, ‘Oh, I’m going to start my business!’ “ – Stephanie laughs. It was 2015 and she started from scratch. She had to learn more about setting up a business legally, tax-wise, etc. She was painting for fun and selling these pieces, promoting them on social media, which were the ground model on which she built her business. “It would have been much more difficult before the social media to get in front of the people” – she says. What she recommends, if you’re just starting, is building a financial cushion that she did not have. “I did not have any money saved and was earning every penny just to pay my bills for the first year. Essentially, I wasn’t able to save anything, but I made it because it made me hungry. You know, I had to work because I had to pay my bills. It’s easier if you have a financial cushion, something to keep you through a hard time.”

So how can painters find clients? Social media, advertising, groups?

“Advertising can be tricky” – says Stephanie. “From my experience, advertising works with repetition”. For example, she noticed that when she bought an expensive ad in a magazine, it had to stay there for three or four issues to gain traction.

“Social media definitely help you find many new people just because of the tagging and sharing abilities” – she admits. If you shared your work on an online gallery or online store like Etsy, it’s optimized for search for everyone, there is so much traffic. If you have your own store on your website, at the beginning you’re not getting a lot of traffic to it, so it might be better to use the existing online platforms like Etsy or online galleries. “You have to start building relationships”. For example, Stephanie has a relationship with The Knot, because it’s a wedding platform and it’s everywhere. “I started advertising with them, but I’m very active in commenting, posting and sharing their content, and I really have a relationship with whoever is managing their social media and advertising staff”. One of her best advice is: “If you want to be helped in getting exposure, help give exposure”. Another way that has been helpful in finding other professionals who also serve your target clients. For example, her clients are brides and she’s trying to serve them through her blog. “It doesn’t initially sell, but it gets interest from different avenues and people I haven’t met before, new followers.”.

Interesting, right? And what does she think about podcasting as a way of getting exposure?

“I like listening to a selected number of podcasts, I follow about 20 of them” – she admits. For sure it’s a good way of getting exposure and promoting your business, but you shouldn’t just try to sell. “You have to serve in a specific way. If I were going to do a podcast interview, one topic that I can see going is how to sell a luxury service to a bride. It’s about having a deeper conversation”.

If you would like to host a podcast, it’s a great thing, but it’s also a lot of work. It’s almost like a full-time job, because of the interviewing, editing, managing, marketing. It’s like your second business. ”A blog is a little simpler” – Stephanie says. “I have a blog, where I just produce content and link to that. I don’t do advertising or anything just yet, but it’s absolutely a way to serve.”

For most starting freelancers, one of the biggest issues is setting a price. What is Stephanie’s advice on that?

“It’s very tricky” – Stephanie admits. “Because it’s based on the perceived value. A painting is worth as much as someone will pay for it”. In some niches, like photography, there are more competitors than in more specific ones, like live painting. “As a creator trying to run a business, you should absolutely know about what your competitors are charging, you should know what people are expecting to pay for similar services. Experience also has a lot to do with it. If you’re just starting out, even if you’re really talented as a painter, you have to understand what other people are charging. If you go to an art festival or you google it, you can see what people are charging, especially for original art, prints are obviously more affordable – it’s the cost of the print mocked up four times or something like that. A lot of people base their prices on size or time. When I first got started, I wanted to charge per hour of painting. But in such a case, there is so much more non-billable time and effort, like marketing, prepping, etc. I could spend 4 hours on painting, but you still have eight hours left out of the day that you’re busy and that you’d like to be compensated for. – Stephanie explains. “When you’re starting out, have an idea about what you would like to be paid.” Her best advice? “When you sell a painting and you immediately regret you didn’t charge enough, because of all the emotional connection that you have with it, charge more next time. It’s a trial and error and it’s the same thing for most businesses”. When you say “My work is worth $10 000” and you don’t sell a piece, then you know you need to reorganize your pricing structure and market to a different market audience.

There is also the perceived market value. “It doesn’t matter what your competitors are charging if you know somebody is going to pay double, charge double. I actually have the whole freebie about this topic”. You can find the amazing content Stephanie prepared for you here.

Are there any characteristics or challenges typical only to painting business?

“In most ways, my particular painting business is just like every other business” – says Stephanie. Like in most business, you have to set the mindset of how to provide value for a customer. It’s not about creating artwork and trying to convince people to buy it. You have to focus on your customer needs or wants. When I’m trying to sell, I don’t try to convince people to hire me, I’m like ‘I can provide that for you’ and that makes it a little bit easier.”

What about the differences? “My job as a wedding painter is to be hired. But a lot of artists, they want to sell the work that they’ve created. They often times paint many pieces, to form a collection and put it in a gallery. In that way a painting business can be challenging as you have to put a lot of time and effort into getting started, you do the work before you get paid.” Once your works are in galleries, you become an established artist, sell your works, prints, and royalties, you gain momentum. “Then there is also the emotional connection” – Stephanie admits. “In most businesses, there is no real emotional connection with the product or services. The electrician can be connected to how they make their clients feel, but not really to their service. Artists and creatives generally are selling a product, for example, the pottery makers, but they made it with their hands and they give it away, there is an emotional connection there. That is also something you should consider in your prices”.

Has it ever happened that the client did not like her work?

“I have had bad experiences because I do customer painting” – Stephanie explains. “If you’re selling a ready painting to a customer or a gallery it’s different because there is not really a connection. With custom paintings it’s different. The client knows what they want already.” Stephanie says that in the past when she had to go back and make changes, it was mostly a result of a miscommunication. “I’m a very outgoing and service-oriented person, which is kind of different from what most artists are really, as usually they are really connected to their work. For them client relations is a tougher part of the job.” Every artist is waiting to see how the client responds. If the answer is good, okay, moving on. If the client responds poorly, it can be challenging to handle that. My personal perspective is: in the one on one business, the customer is always right. How you respond to their negative feedback sets the tone for the closing of your job with this person.” Her experiences? Once she got hired by the bride’s mom, so ultimately, she wanted to make her happy as well as the bride. When she sent her the photograph to approve, the client said: “I don’t know what it is about it, but I’m just disappointed”. “It was heartbreaking because I was very proud of this painting” – Stephanie admits. What did she do? She called the bride’s mom and they had a conversation. She tried understanding what was wrong, as often clients may not be able to put it into words. She put more time into the painting, tried adding more details, going outside the bounds of the contract. Stephanie did everything to make the client happy, even if that meant working more on the painting. After all the changes the client was still disappointed. “At that point, my heart was in my throat. That moment I was at a loss because she was unable to communicate what she needed exactly, all she was telling me was that she just wasn’t happy”. How did she handle that? “I told her, I wish we were on the same page. I said: ‘You know what? I actually am very proud of this painting. I put a lot more detail on everybody’s faces. I did and went beyond the bounds of our agreement to try to make this right. I’m so sorry that you’re not happy’ and I offered her a partial refund. I was trying to make her feel better about the situation.” The client politely declined the offer and told Stephanie to send the painting to the bride. “Will she be a client again in the future? I don’t know but at least I feel like I did everything I could to salvage the situation.”. How you solve difficult situations sets the tone and influences your reputation. “It’s all about how you recover from bad feedback or critique.”

And what about the bride? She loved the painting!

Stephanie admits that she had other difficult situations, but from each of them she learned a lesson that helps her improve her business every day.

What was the most disastrous situation that has ever happened to her during live painting?

Two years ago she was painting at a wedding outdoors. “Sometimes it can be absolutely beautiful, but at times it can be absolutely miserable” – she admits. It was very cold and windy that day. “I went inside to use the restroom. When I was inside, the wind has blown my canvas and knocked it over my entire easel. My wash cup, paint, my brushes, business cards went flying everywhere. The water from my wash cup, which broke, splashed all over the painting. So the hour of work that I had put in for the live wedding painting was destroyed”. Considering she only has about 5 hours to finish the painting, every minute is precious. “The first layer was completely washed off, streaks, paint everywhere, it was embarrassing. It was miserable because then I had to start over. I had to dry that off and just keep going. And I had to use a tiny little paper cup for my wash cup.” Now Stephanie laughs of it all. “You know, I learned my lesson. Now I’m a lot more prepared if I have to paint outside, I’m more specific about where they set me up. I know I need coverage, I need an outlet and a heat source. These are things that you know about your job and how you can do your job the best way. You learn because bad stuff happens.

What about the good stuff?

“I don’t have one special memory. Every time I deliver the painting and the clients’ reactions when they love it, it’s the best. I forget to ask for a check. I wish I could pay my bills of the joy that they show, that’s so worth it for me. That’s why I do it because it makes people so happy”. Stephanie laughs and also adds: “It really doesn’t do anything to me if a client begrudgingly makes payments. Yeah, I made the sale and my business has to go on. But it’s the emotion that drives me.”.

So what is her advice for people who haven’t started yet but love to paint and would like to turn it into a job?

“Understand how it works and please, always create. Now that painting is my job, I mean, I tell people all the time I need a hobby” – she laughs and I so understand her. “Learn what you like to do, try new things, be creative and don’t let fear hold you back from starting and trying new things. You can’t be happy nor creative if you’re not making any money. The idea of the starving artist is over. With social media and the Internet, I can even sell exclusively to people in different countries and I never have to leave my couch. We have so many opportunities to sell and to connect with other people.” Stephanie advises understanding who your target market is equally important, who your target audience is not as “If you try to sell to everyone, you sell to no-one”. “Understand who you’re trying to sell and then understand that you’re going to have to say no. You’re going to be pulled in many different directions, but try to focus down”. She also suggests creating something every day, but also understand when the creative juices flow. “When the creative juices are not flowing, rest and use the other side of your brain. For the last 2 days, I was not feeling like painting at all. I can’t tell you how many times I sit down to it, but it wasn’t until 10 o’clock last night that I started a painting that I’ve been trying to start in 2 days. However, I got up and I went to the other room and I worked on my website, I did designing things, I sent emails and I ran my business. Understand, the ebbs and flows of your creativity and work with that, that’s really important.”.

How did you like my interview with Stephanie? Do you have anything to add or still have questions? Or maybe you could share your story of how you become a freelance painter. Let us know in the comments. You can follow Stephanie on Instagram and on Facebook. You can also read more about her story on her website: All of the pictures presented come from Stephanie’s Facebook Page.