Today we’d like to introduce you to Ashlyn Wilderness.
Hi Ashlyn, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstories.
Origin story! How fun. Let me begin with the basics.
I’m a freelance artist originally from the midwest. I specialize in organic, colorful illustrations.
I’ve been drawing and creating fictional worlds since I can remember. I began working as a creative professional at the age of 17, and after dropping out of art school, I became serious about the medium of illustration. However, shortly before the pandemic began, I decided to close down my first small business and work instead in the field of nonprofit addiction recovery.
Talk about a career shift–right? However, I’ve always thrived at the intersection of community and creativity, regardless of the job title.
Addiction recovery was the ‘espresso’ of careers: intense, saturated with chaos, each day a mix of exciting or heartbreaking. (I won’t share explanatory anecdotes here, but if you know, you know.)
Part of my work included career coaching. I would walk men & women through the vulnerable, beautiful, impossible task of discovering what they wanted to do for a living. I’d ask probing questions: What have you always been good at? What is something that you’re passionate about? If money weren’t a concern, how would you spend your days?
It’s hard to ask such probing questions without considering them yourself. It was something I wondered about, too: for 40 hours a week, was I actually doing what I felt called to?
While I loved the actual work of my position, I realized that the bureaucracy and rigidity of the nonprofit was eating me alive. No– I had always been more of an adventurer, a dirtbag, a trailblazer. I looked around and didn’t recognize myself: since when did I begin to own all this business clothing and use words like ‘propensity’ in daily conversation?
The beginning of the end. Once you open the box of curiosity, it’s hard to close.
So I quit. I didn’t tell any of my coworkers or acquaintances where I was going but instead shared that I had something ‘new’ coming, a ‘secret’.
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?
The most challenging thing about the whole process was actually taking the leap and quitting my job.
It’s one thing to dream about starting your life over, but to actually do it was mortifying! There was a space of about two months between deciding that I would quit and the actual conversation with my supervisor.
This is the part of the story where I felt my training montage should begin, Rocky style. But, no. I fell into a deep depression.
While my departure was good, it was also a life-altering change that shattered my own expectations of my future. Work as intense as addiction recovery hot-glues itself to you. Unpeeling yourself is like removing parts of your skin.
I laid in bed for days, draining the battery on my laptop and my phone… at the same time. I had ravaged two boxes of chocolate caramel candies, covered the house in takeout trash, and laundry laid on the floor like a carpet.
Some would call those depressing days a waste of time, but really, the release and rest gave me moments of clarity.
This was my hope-filled realization at the bottom of the dark chocolate bag:
The people I met, stories I told, and opportunities I had in my years outside of career creativity weren’t a diversion from art, but a fulcrum that captured my imagination to tell better stories, calling me to return to the warm embrace of mixing color and words.
When I picked up the pen again after years of dormancy, it delighted and shocked me that the art was different. It was rough yet vivid. Even colors as plain as white were dappled with blues and pinks and greens.
My new venture ‘Fairweather Creative’ was born out of that fulcrum, the space between pain and purpose, filling simple forms with uncut color. The fun piece of this interview is that the launch of my business is still weeks away, but I’m excited to see what happens next.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
My primary medium is digital painting. I began as a portrait artist years ago, but have a newfound love for landscapes and still life.
In my repertoire is also animation, graphic design, logo design, public speaking, writing fiction, videography, photography… and so on! Hopping between forms of art is a joy for me.
What sets me apart as an illustrator is the collision of vibrant color with semi-realistic style and dynamic linework.
I’m open to commissions, though most of my income as a creative comes through the selling of prints, posters, and cards.
Pricing:
- I sell my prints for around $30, and my commission fees start at $200.
Contact Info:
- Instagram: https://instagram.com/fairweathercreative
- Linkedin: www.linkedin.com/in/ashlyn-wilderness
- Other: https://www.etsy.com/shop/fairweathercreative

Image Credits
Justice Lucas (@justice_lucas_)
