With a client base like Hilton, 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 DC 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.

Sheehey designed a set of four limited-edition collectible keycards for Hilton. Her original designs include a cozy hotel suite overlooking the Capitol, bustling Union Station filled with holiday travelers, a quaint stroll down a Dupont Circle sidewalk, and a signature pattern of food and cocktails.

We were lucky enough to stop by her light and airy (and delightfully pink) studio to chat about her work. We also spent a lot of time playing with her dog. Like Sheehey’s watercolors, it was magic in all the right ways.

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 open 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. 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!”

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 somedays 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…”

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

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 DC in early 2017 and I feel as I’ve gotten to know DC better and as my art style has gotten better, I would love to do a bigger map of DC.

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.

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?

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.


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