We caught up with the brilliant and insightful Chelsea Willett a few weeks ago and have shared our conversation below.
Chelsea, appreciate you joining us today. Almost all entrepreneurs have had to decide whether to start now or later? There are always pros and cons for waiting and so we’d love to hear what you think about your decision in retrospect. If you could go back in time, would you have started your business sooner, later or at the exact time you started?
It’s hard to say if I wish I had started it sooner because the journey was rich of meetings, beginnings and endings that all informed my work and life.
I originally launched solo and full time in 2018 but had been working as an artist since 2002 and as a graphic designer since 2013. I quit my job and hoped to make it hustling art shows and popups and supplementing with graphic design. The momentum was great at first and I did so many art shows and popups for 2 years that I definitely burned out. It was also expensive financially and energetically and not all of them had a great return. I ended up leaning in graphic design much more and allowing my art life to breathe and join the popups that I fancied.
The hard part about pulling ones whole income from working as an artist is that the joy and love of art for art’s sake drains out. This was actually the big factor holding me back for so many years. I had worked professionally as an artist since 2002 from murals to signs to commissioned paintings but always kept a job so that I didn’t rely on it solely for my income.
In a lot of ways I wish I had trusted and believed in myself sooner but I don’t think it’s helpful for me to look back and feel bad about the journey that did happen.

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 grew up among artists and had a very openly creative house. I was allowed to get lost in art and also start projects and leave them out to come back to when I felt the urge. I mostly kept it to myself and my house as I grew up but when I graduated high school, I really started to pursue it. I did attend formal art school and studied graphic design many years later but mostly followed and tried whatever was exciting me in the creative world.
I still do a lot of art services for people. A short list is: murals, signs, chalkboards, illustrations and commissioned paintings. As far as graphic design goes, I specialize in branding and web but also offer print, digital, content creation and curation. Graphic design is such a big umbrella that my portfolio is incredibly diverse.
I help people find their voice and share it through their branding alongside helping strengthen branding that already exists depending on the client. This also involves helping them stand out and become seen and remembered by their ideal audience and clientele. My work relies on weaving their offerings and work into community and make connections that are meaningful.
Due to my art background I have a very diverse set of skills that sets me apart from others. It’s rare when a client doesn’t ask me for illustrations or an artistic touch. I’m also very community driven and personable and people refer me just based on the connection we create when working together. A lot of people struggle to show themselves on a website and share their story so it’s crucial that I can help cultivate a safe and non judgemental space to accomplish the work and help them step into the light.

Do you think there is something that non-creatives might struggle to understand about your journey as a creative? Maybe you can shed some light?
There are many things that I see non-creatives struggle with when working with me or even alongside me. Mostly it comes across as distrust which can be hard to navigate. Even with a robust, variated portfolio, it’s only natural to be weary when one is spending a high amount for themselves or their business. The reality is that just because you have a website and branding, it doesn’t always mean you will be successful. There’s so much more to the picture.
I generally lean into to teaching clients and others about how creativity in storytelling, illustration and sharing oneself can feel so connective to the person on the other side. I also find it’s helpful to ask them about a time when art, branding or even a poster offered connection or experience for them.

What’s a lesson you had to unlearn and what’s the backstory?
The biggest and hardest lesson I have had to learn over the years is that my journey is absolutely unique to me. I can’t set up my business like anyone else. I also can’t create the way others do.
A great example is in graphic design and the popular fads. I would catch myself getting caught up in some of them even though I didn’t like them and I definitely did not like looking like others. I thought if I followed the fads I would be successful like my fellow colleagues.
This has happened and can happen in any aspect of my creative life and business. Now I know better and realize that my strength is to actually not look like others and stand out.
Contact Info:
- Website: https://www.serpentweaverdesigns.com
- Instagram: @chelseawillett_designs





