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

Damon, appreciate you joining us today. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.

A few years ago, I made what most people would consider a questionable life choice: leaving a stable, full-time job in my 40s to pursue art full-time.

I had a dependable career in retail logistics and supply chain management, with predictable hours, health insurance, and a 401(k) I probably never contributed enough to. Married, kids, plenty of debt and all the usual life chaos. On the side, I’d been making art for years. Nights once everyone went to bed, lunch breaks, weekends, and whatever scraps of time I could find in between. It started as a passion project I never seriously imagined could become more, until it did. Putting my art into the world for the first time was freeing, and it quietly changed everything.

I started small, selling a few prints and stickers here and there and slowly grew my business while still holding down the day job. I never really believed I’d get to make the leap full time (the inner cynic was loud), but eventually, the momentum carried me there. Now, I sell my work online and at events, have a network of retail shops that carry my products, and a growing client list I genuinely enjoy working with.

That risk, walking away from stability to chase the thing I actually cared about, turned out to be the best decision I’ve ever made. I get to spend my time doing work that fulfills me, even if I still occasionally wake up in a cold sweat wondering about taxes, inventory, or whether that weird keychain I designed was a terrible idea.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m a Portland-based illustrator and the human behind SheeleyCo, a small but mighty art brand built on a mix of nostalgia, nature, quiet reflection, existential weirdness, and subtle (or not-so-subtle) humor. My work is heavily inspired by mid-century design, old ephemera, and that strange blend of peaceful and slightly unhinged energy you get from being a thinking person alive on Earth right now.

Before I was doing this full time, I worked for longer than I care to admit in logistics and retail operations. It was work, but it didn’t exactly feed the soul. Art was something I made time for whenever I could, even if it took years to figure out what I actually wanted to say and how I wanted to say it. Eventually, I started sharing what I made, and things just grew. People connected with the work. I leaned in. One thing led to another, and now here I am, self-employed and still mildly confused that I get to do this for a living.

SheeleyCo offers a range of illustrated goods, including prints, stickers, patches, apparel, enamel pins, stationery, keychains, and other things I probably shouldn’t have figured out how to manufacture but did anyway. I also work with clients on select freelance projects like book covers, branding, and album art. The common thread in everything I make is a mix of intention, curiosity, and a desire to create something that feels warm, human, and honest. My hope is always that someone out there sees a piece and thinks, “Oh. That’s me.”

What sets my work apart I think, is that it holds space for both the beautiful and the weird, sometimes all at once. I’m not chasing trends or aiming for perfection. I just want to make things that feel real, like something you’d come across in a little shop in your favorite part of town, and for whatever reason, it just clicks. It feels familiar. Like it already belongs to you somehow.

What I’m most proud of is simply getting here. I’ve built something meaningful, slowly and intentionally, while staying true to my voice. If you’re a potential client, follower, or someone who wandered in here by accident, I hope you find something that makes you laugh, feel seen, or feel just a little less alone. That’s the whole point.

Okay – so how did you figure out the manufacturing part? Did you have prior experience?

I do not currently manufacture any of my own goods. I have always worked with outside vendors for that. From day one, I knew I wanted to focus on the creative side and partner with folks who could handle the production side with care and quality. There was definitely a lot of trial and error in the beginning, though. Finding vendors that matched my standards and understood the tone of my brand took time. But once I found the right partners, often small businesses themselves who are equally invested in doing great work, it made all the difference. I’d much rather support someone who understands the dynamics and wants to build something great together.

Coming in with my background in retail gave me a solid foundation in managing vendors, timelines, and quality control. Different industries but the same skillset. So I approached my own manufacturing with clear expectations, good communication, and a willingness to tweak things until they’re just right.

Biggest lessons? Sample everything. Build in more time than you think you’ll need. And don’t underestimate how much easier your life gets when you work with people who care about the details. These days, I have a trusted network of vendors who help bring my work to life, so even if I’m not the one physically producing the goods, every piece still reflects my hands, my vision, and about 47 tabs open in Photoshop and Illustrator at any given moment.

If you have multiple revenue streams in your business, would you mind opening up about what those streams are and how they fit together?

I’m a firm believer in having as many sources of income as one can reasonably manage. That way, if one area slows down for a quarter or two, there are still other ways to keep the lights on during the inevitable ups and downs.

I sell my goods online, in person at markets and conventions, and through over 150 retail shops via my wholesale channels. I also take on freelance projects for product packaging design, album art, book covers, apparel companies, merch for events, and the occasional weird-but-fun one-off commission. On top of that, I also offer licensing of my existing artwork and I’ve slowly been exploring digital downloads like fonts and other assets.

Having multiple revenue streams has made my business more sustainable, and it keeps the work varied and creatively interesting. One day I might be fulfilling wholesale orders, the next I’m sketching out concepts for a band’s new tour merch. Keeps things moving, and keeps me engaged.

Contact Info:

• Website: https://sheeleyco.com
• Instagram: https://instagram.com/sheeleyco

Image Credits

Not applicable – all self taken