
Today we’d like to introduce you to Jess Reddy.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
I’ve been making art in some form for as long as I can remember! Since I was a kid I’ve been painting, drawing, sewing and designing. I was lucky enough to have parents who always encouraged my creative pursuits. My Dad is an artist at carpentry and has almost always been self employed, I was blessed with his creative entrepreneurial spirit. He’s hand made so many canvases for me to paint on a budget as a young artist and taught me the importance of DIY. My Mom is my biggest fan, she’s endlessly supportive of me and always has new ideas for how I can get my art out in the world. They always helped me believe in my abilities and instilled a lot of hustle in me so I would never doubt that I could do anything myself. So when the pandemic hit, I lost my job and had to make something new happen for myself. I wanted to figure out how I could become a legitimate working artist and be my own boss. While stuck in quarantine, I was able to dedicate more energy to expanding and improving my art. During those few months, I taught myself how to digitally illustrate and design using an iPad and iPencil. Going digital has opened up so many doors for me and my art so I’m able to work as a freelance artist for the first time in my life!
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
My biggest challenges have been getting the strength to share my art and price it fairly. I feel like it takes a lot of convincing for most artists to believe in their work in general, so it’s hard to present it to the world for sale and not feel vulnerable. Sensitivity and vulnerability have always been issues for me and they’re big themes in my work as well. I’ve had a hard time opening up and sharing my art in the past, but every time I get a positive response or make a sale, I gain a little more confidence in my worth. The feedback I get from showing my friends and family my art means the most to me. They’ve all been the biggest influences for me to just get over my doubts! Every time I post a new piece they show up with so much love and support, it gives me the strength to keep at it. I look at vulnerability as a good thing now. If I didn’t let myself be vulnerable, I wouldn’t get these chances to receive their love and support. So I don’t even hesitate to share anymore, it’s easier to do knowing that the people I love have my back.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
I love to make digital illustrations and physical paintings and I also have an online store where you can buy prints of my artwork! Recently, I sold some art prints and two of my biggest paintings ever to a restaurant group that I love, so I’m excited to see those hung up in some of their locations eventually. Big achievement for me! I’m a contributing artist for a charitable print sale program, run by the basketball lifestyle brand Local Hoops. All proceeds from the sales go directly to helping a small business or community-driven organization in need, which I’m really proud to be a part of. I’m also lucky to make art for a non profit sex workers outreach program called SWOP that offers community education and peer support for sex workers in New York. I’ve just started making custom pet portraits, I love animals and creatures, so I’m excited to experiment drawing those more. Since learning to make digital art, I’ve been able to expand my portfolio like crazy and get a ton of freelance work. I’ve been able to design merchandise, logos, social media graphics, clothing patterns, tech packs, spec designs, brand guides and more for companies I’ve connected with online. This year I would like to move toward exterior and interior painting for commercial businesses and restaurants, paint my first mural and find new ways to get my art out into the world physically!
Can you talk to us a bit about the role of luck?
I feel very lucky in a lot of ways. I have people who love and care about me and that’s enough to feel lucky forever. But I owe a lot to the people who have helped me get where I am, and I have to remember to give myself credit for the good things I’ve made happen myself. I can’t diminish my accomplishments by chalking them up to luck. Myself and all the people who have ever helped me further my art career have just worked hard and believed and we made it happen. That’s not luck, that’s dedication, but I feel very lucky anyways.
Contact Info:
- Email: [email protected]
- Website: Etsy.com/shop/WhyNotPrintShop
- Instagram: Instagram.com/jessreddy

