Meet Elizabeth O’Leary

Alright – so today we’ve got the honor of introducing you to Elizabeth O’Leary. We think you’ll enjoy our conversation, we’ve shared it below.

Hi Elizabeth, thanks for sharing your insights with our community today. Part of your success, no doubt, is due to your work ethic and so we’d love if you could open up about where you got your work ethic from?

My father threw nickels around like manhole covers. That is to say, the man was FRUGAL. My siblings and I did not receive any allowance or spending money. (He said, “We don’t pay you to be a part of this family”, lol). We definitely had to make our own magic. So, at age of 11, I started babysitting the neighborhood kids, for $1.25 an hour. And that began my illustrious history of hustling to make the dollars. In college, I was an R.A. (resident assistant) in the dorms because that paid for my room and board.

I spent 30 years in Chicago as a successful, freelance corporate television producer, writer and director. As a freelancer, or any self employed person, if you don’t hunt, you don’t eat. I was single until I was 40 years old, and it was critical to be self reliant. There is no such thing as a paid sick or vacation day, employer paid social security or health insurance. So having a substantial work ethic was key to surviving in that industry and also to being the leather artisan that I am today. But once your clients realized you embodied the values of good time management, dependability, self discipline, team work, punctuality, positivity, and hard work, they would hire you nonstop for several years at a time. For thirty years, clients such as Amoco, Allstate, Motorola, Kmart, Craftsman and Sears trusted me to tell their marketing stories with their CEOs, celebrity spokespeople and employees.

At a certain point, I got burned out of the 2D digital world and longed to make something physical, long lasting and tactile. I decided to pivot my storytelling skills into pursuing my love of creating upcycled mixed media art and eventually, leatherwork. One day in 2015, on a whim, I signed up for a beginner leather making class. I was hooked immediately! The smell of the leather, the buttery glide when cutting, the enormous sense of possibilities made me so excited. I knew I wanted to switch my creative efforts to include leather work. By the time I took the plunge, I was living several hours away from the leather school. Knowing I would have to teach myself leatherwork was inconvenient, but not a deal breaker.

Luckily, the tremendous work ethic I had established helped me make the transition from video producer to leather artisan. But it wasn’t easy. I had made a major career change at age of 50, moved from a city of 3 million people to one of 100,000, and I didn’t know a single soul. It was a pivot that tested my resilience daily.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

My art company, Undercover Popular, was formed in 2011 and continually evolves to allow several different product categories. Today, we are known for our leather wallets, quirky clutches with unique clasp hardware, whimsical keychain/purse charms and home and office accessories.

For years, I had collected vintage handbags from the 1940s-1970s. Eventually, the market changed, and the vintage handbags I was able to afford were those that no collector would bother buying. They were imperfect with scratches, marks or other blemishes. Having been raised by parents that lived through the Great Depression, I intrinsically knew they could be revived with a little bit of imagination and creativity, so that another generation could appreciate and use them. They needed a little extra “oomph”! And I was just the gal to do it! I upcycled these bags with unusual vintage and hardware elements.

During the hunt for these bags at estate sales, I would always find other cool vintage items that I wanted to incorporate into the refurbished handbag. With the vintage bags being the base layer, these found objects became my collage elements. Often I used old hardware because of its graphic shapes and bold look. I had developed an aesthetic that was completely my own. The storytelling morphed into an revamped object that could be seen, touched and had a functional purpose as well. I sold these one- of-a-kind bags to retail boutiques, art museum gift shops, and individual clients in the USA, Canada, Europe and Australia.

The genesis of Undercover Popular, my art company, started with this idea. Although today we are focused more on creating new leather accessories, it all started with upcycling and a commitment to slow fashion, and those are core values we continue to utilize whenever possible.

My evolution into leatherworking introduced another element to further extend the range of my creative expression. My use of collage challenged the boundaries of traditional leather making in new ways. By utilizing upcycled and found objects, punctuated with unique hardware, I tell stories through creatively handmade leather fashion handbags, jewelry and accessories and home decor items. My work is inspired by funky geometric shapes, superior craftsmanship and graphic composition. Using old world techniques combined with an eye for today’s vibe, I focus on creating bold, beautiful and layered pieces that showcase a love of classic style with a touch of whimsy.

Undercover Popular is currently focused on finding additional established wholesale clients and charming boutiques, as well as continuing to participate in local upscale art shows. I love when one of my products finds the right owner and they are beyond excited to purchase it and call it their own. We are small batch artisans, not mass produced, and each piece is unique, usually hand sewn, and will last for many, many years.

We are looking forward to moving into a much larger, 1800 square feet production studio in late summer 2024 in downtown Elkhart, IN. This will give us the opportunity to have more equipment in use, and scale up production and productivity. In addition, we will have an area with product samples for wholesale buyers, and lastly, potentially have classes for the general public later this year. We are excited to uplevel our business and expand our product lines!

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

The three most important pieces of advice that helped me and my career as a leatherworker are to lean into failure, stay curious and don’t deliver any product that is less than stellar (Quality Control).

You might think that leaning into failure is not the way to be successful, but it’s crucial for any artist. Oftentimes, we are our own worst enemy. Most artists are naturally insecure about their art. Imposter syndrome and the tyranny of expecting perfection are only going to sabotage your efforts. I’m not saying it’s easy, but you have to learn to get out of your own way. Leather is so expensive, and once it is cut or sewn, there is no ripping out the stitches and starting over- that piece is somewhat ruined. So learn to be comfortable with failure, and even embrace it. Fail better the next time. Especially being self taught, it’s going to be pretty rare that you get a pattern or finished piece absolutely perfect on the first try. It’s all part of the process. So fail fast, and fail often. I don’t mean sitting around all day and failing but you should be quickly iterating, learning from your mistakes, tweaking, resetting and trying again. I even went so far as putting a banker box in the corner of my studio and labeling it “The Failure Box”. If a piece didn’t turn out, so what! There is an old Asian adage that tells you to “Fall down seven times, get up eight.” I would throw the problematic piece in the box, forget about it and move on. Sometimes, I would go back to the box and repurpose the leather or just pull it to compare it to my now finished and perfect item. There is a great book called, “Failed it! How to Turn Mistakes into Ideas and Other Advice for Successfully Screwing Up”, by Eric Kessels. I can’t even tell you how many times I had a version for an upcycled purse, but made an execution mistake that forced me to go in a different creative direction– that ultimately produced a finished product that was way cooler than I initially imagined!

Next, it’s vital to stay curious and flex that creativity muscle. You can have twenty years of experience, or one year of experience for 20 years. You need to keep learning and growing and developing skills. Naturally, from time to time, everyone gets a creative block. The book, “The War of Art: Break Through the Blocks and Win Your Inner Creative Battles”, by Steven Pressfield is a life saver. This book gives your brain a new perspective on resistance and procrastination and how to get out of a stagnant rut.

Another great book is “Big Magic, Creative Living Beyond Fear” by Elizabeth Gilbert. She has a unique take on the nature of creative inspiration and the “muse” that will completely change how you think about the creative process.

Lastly, Quality Control is vital to your brand excellence. “The price of excellence is eternal vigilance.” As an artist, you ARE your brand, and every product reflects the standards you hold dear. It is better to throw away a product than to have it negatively represent your brand. Luckily, if your work ethic is as strong as mine, this vigilance will just be second nature to you. Every leather accessory that Undercover Popular produces is the best I can possibly make.

How would you describe your ideal client?

The ideal client for Undercover Popular is a retail boutique or individual that wants to offer or own high quality, unique, handmade leather items.

Our premium, handcrafted leather home decor and functional art accessories help retail store owners who want to avoid carrying run of the mill, boring, massed produced product lines. Through Undercover Popular, they can source creatively built and fashion forward leather products by a local maker. In an increasingly automated and digital world, most of our items are hand sewed, using old world techniques combined with an eye for today’s vibe. We will collaborate with store owners to design small batch artisanal, unique custom products geared for their clientele and supplemental merchandise.

We love to supply retailers and individuals who value locally handmade craftsmanship. Undercover Popular offers a fresh spin on leather goods by offering a lower price point, creative design elements and an original sense of style.
My brand of creativity is uniquely me; I love to create visual patterns and graphic compositions on leather, as opposed to the very staid traditional western leather goods.

Contact Info:

• Website: https://www.undercoverpopular.com
• Instagram: @undercoverpopular
• Facebook: (Undercover) Popular
• Linkedin: Elizabeth (Crowley) O’Leary