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With a client base like Hilton Hotels, SOREL footwear, Fabio Trabbocchi Restaurants, La Croix and Ralph Lauren (just to casually name a few), you wouldn’t be remiss thinking Riley Sheehey is an artist with decades of connections. Her water color illustrations, which garner a following 25,000+ strong and net her thousands of likes on Instagram are precise and elegant. They feel like the work of someone who has been carving out their niche for a long time, but Sheehey, with her love of delicate colors and fairytale-esque scenes is a relative new comer to the D.C. art scene. Since transitioning into a full time artist in June of 2017, she’s been pumping out her trademark whimsical portraits and playful patterns, while learning a lot about what it takes to run a small business along the way.

We were lucky enough to stop by her light and airy (and delightfully pink) studio to chat about her first few years of full time work (including that impressive client base), her love of thrillers and her secret desire to paint a Billy Joel themed series. We also spent a lot of time playing with her dog. Like Sheehey’s watercolors, it was magic in all the right ways.

In the Artist Studio with Riley Sheehey is presented in partnership with our friends and partners at Hilton.


When did you start illustrating?

It was the summer of 2014 and I was on summer break from teaching. I just started painting Mason jars that I had found. I’d knew somebody online who opened an Etsy shop and I thought, maybe I could do that in my free time! So I started painting these Mason jars and I thought that I was going to be able to sell them… and I wasn’t.

So you were just doing it for fun?

Yeah. I opened the Etsy shop, I put the Mason jars on it… and I had made some art for fun over the last couple of years. In college, I was an art education major, so I had taken a couple of art classes. I literally just put everything I had drawn or painted on my Etsy shop and nothing sold. That’s what you kind of figure when you’re just taking stuff off your wall! But I was like, “Oh, this would be such a cool thing to do!”

What did you teach?

My first year, I taught fifth grade and middle school history. Then an art teaching job opening up, so I went to the principal and asked her if I could switch to art. So, then I taught art and resource for five years.

That’s a long time. Do you ever miss teaching?

Yes and no. I miss working with kids, especially when I visit with friends who have younger kids. I miss just doing arts and crafts with them, but I think I’m much better suited to what I’m doing now.

Were you drawing as a kid?

I always loved to draw, but I never thought I was going to do this as a job. And it wasn’t something that I did daily. During my first year of teaching, it felt like I was in over my head, so I didn’t do any drawing or painting… or any artwork at all. Once I had been teaching for a couple of years, and I had some of my lesson plans written and all of that, I had a little more time and that’s when I started getting back into it.


But you’re a full time artists now, so what’s your schedule like?

I wake up every morning around 7 a.m. and I get the dog up and go for a walk. I usually get started around 8 a.m. I eat while I work a lot of times, like I’ll eat while I answer emails, but I work pretty much from 8 a.m. to 4:30 p.m. or 5 p.m. It’s been a little earlier because it gets dark now, and then I’ll go for a run.

When you’re working, is it straight drawing and painting from 8 a.m. to 4 p.m.?

I’ve tried a bunch of different things. I’ve been doing this full time since June of 2017. I think I kept telling myself, while I was doing it and also teaching, that I’m not going to be stressed at all anymore… I’m going to have so much time when I do art full time. What I didn’t realize, which is a great thing, is that as I stopped teaching I started taking on more projects. I think I probably took on too much at first. I had to sit down at the end of 2017 and figure something out.

I started 2018 taking half as many projects and scheduling them farther out. That way if something like the Hilton project came up, I could take that project without having to stay up until 3 a.m. working. That’s made a big difference for me.

Depending on the day, I’ll write one or two emails and shoot them off, but some days I realize I’ve spent the entire day writing emails. That gets me so frenzied, because it’s less tangible for me to look back on and reflect. It’s easy for me to say, “Oh I did this project and that project…”

When and how did you decide to leave teaching to become a full time artist? How did you get to that point?

It was the fall of 2016 and I remember calling my mom because Washingtonian had posted something that I drew. It was a huge deal for me, but they posted a little drawing I had done of Rose’s Luxury. I think in that day I got a couple of different emails about custom work… and then I started getting more. Before, I was doing one or two projects a month and the turn around was maybe a weeks time, but I started to get a queue of projects. It’s that gradually and then suddenly thing. All of a sudden I was working on weekends. At first, I was only working a little on the weekends and then I would set my deadlines for the weekend…

It got to the point where I went to my principal, who I had developed a really good relationship with and had worked with for a long time, and I sat down with her and said, “How would you feel if I started taking Mondays off in January and went part time?” Having Mondays off gave me a much better idea of what it would look like if I did art full time. I realized around February or March that I had more work than I could finish on a Monday. So I sat down with my husband, who used to be an accountant, and he looked at the amount of money I would need to make. It was going to be tight, but I realized this was the time in my life to do it.


You have a bunch of different clients you work with, we talked about Hilton, but also La Croix, Ralph Lauren, etc. How do you decide who you’re going to work with?

This is something that has changed a lot. When I first started working, I took anyone that wanted to work with me. I did that for a long time. Now if somebody reaches out to me and I think they’re a good fit, then I work with them… but it depends. For instance, I tried doing place cards for weddings. I don’t know calligraphy and I’m not a calligrapher, I do fake calligraphy. I found myself really overwhelmed. Plus, if someone asks me to do something and I know someone else who can do it better, I’m going to recommend them. Someone reached out to me a few weeks ago and they were looking for an artist to do their vows on 16×20 paper. I know it would take me such a long time do to that and I wouldn’t do as good of a job as someone else.

Like the Hilton project, when a company says, “This is what we’re looking for,” but I have the ability to get creative and come up with different scenes… That’s when I know it’s going to be a good fit.

It’s the leeway to do your own thing.

Yeah, definitely. I also do a number of commissioned portraits. Those are great because they’re super straight forward. I do a limited number of those.

What do you listen to while you work?

It’s pretty embarrassing! I listen to a lot of audio books, that’s not the embarrassing part, but I listen to anything you’re going to find on a bookshelf at the beach. I love any kind of crime thriller. I asked a couple of people what books they would recommend, and I was looking at the recommendations and I was like… These are real literature! I’m looking for something where I can go to the bathroom and get something to eat and I haven’t missed anything!

What are you listening to now?

I just finished a book called Let Me Lie, which was really bad. It was actually too bad. There’s a level of junk food reading, which I like, but then there’s a level below. There is a line. Last week I finished one called The Other Woman and that was really good.

We just threw a true crime festival, are there any real crimes that you’re particularly fascinated by?

On My Favorite Murder, they recently talked about the Lululemon murder in Bethesda. I read a book on that a couple of years ago, some guy from Washington Post had taken a sabbatical to write about it. It’s written more like a news article, it’s very to the point, but I thought it was really interesting.


To get back to your art, do you have a holy grail piece? Is there anything you’ve wanted to create, but you’ve never been able to nail it or you haven’t had an excuse to start it?

I’ll think of stuff sometimes where I’ll be like, it would be so cool to do this, but I don’t think I have the time… I have two examples, one is more serious and one is silly. I did a map of D.C. in early 2017 and I feel as I’ve gotten to know D.C. better and as my art style has gotten better, I would love to do a bigger map of D.C.

The silly one is based on the Billy Joel song “We Didn’t Start the Fire.” I always thought that if I had all the time in the world, it would be so cool to do an illustration of all the things in that song. It would be such a ridiculous thing. There would be no reason for me to do that. From a commercial standpoint, I cannot imagine the niche of people who would be interested in hanging that in their house that would be very big.

You’ve sort of brought this up, but how do you know what’s going to do well with your audience? How do you know what they like?

That’s a really good question and it’s one I think about a lot. When I got started, like anyone does, you draw what you like. It will probably sound stupid, but I’ll probably never get back to the point where I’m just drawing for fun, because you can never get other people out of your head. Like, I wonder if other people will like this? That’s something I think about when I can’t sleep at night [laughs].

But I keep a notepad on my phone of different ideas. I was running last night and I kept stopping because I was listening to Christmas music and I kept coming up with things. I’ll add stuff to my Pinterest board, but I’m a nut on Instagram. I should spend less time on it, but I spend a lot of time seeing what other people are posting and what engagement they’re getting.

What gets the most engagement? What’s almost guaranteed?

When I think of a good idea… Like I did some candy corn people a couple of weeks ago and I knew that one was going to get more engagement. Any time I use real objects. Also, people love the holidays. Growing up, my mom used to say, “I hate how commercialized Christmas has gotten,” and now I always have that in the back of my mind! But I love the holidays. Drawing more Christmas and Hanukkah stuff has gotten me more excited about the holidays.

If you could change anything about D.C.’s art scene, what would you change?

I don’t know if I’m a good person to answer this question! I’m such a homebody that I wish I would put myself out there more, as far as meeting people and networking. I know I’m not answering your question, but I think what’s so great about the D.C. art scene is that it’s so much more accessible. I’ve met a couple of different artists through the few events I go to, one of them is Cris Logan, and she is so wonderful and so warm, I just feel like people are very welcoming. From an outsider perspective, when I think about the New York art scene, it seems too cool for school… I think D.C.’s doing a great job.

Sheehey designed a set of four limited-edition collectible keycards for Hilton, available at 60 DC-area hotels when you book the Weekend Like A Local package from now through March 31, 2019. With this package, guests can eat and drink their way around the Nation’s Capital and enjoy 50% off Sundays and special offers from several local area restaurant.