My name is Cy Whitling, and I live with my partner and dog in Washington. I’m an illustrator, gear writer, and mountain biker. I like to say I have a hilarious collection of part time “dream jobs” where I mix painting and writing to mostly make a living, mainly in the bike industry. 

I didn’t set out to be an illustrator. In high school, I took one watercolor class before being pressured to drop it and replace it with a weight training elective. But all through high school and college, I doodled non-stop. I filled the margins of my papers and drew on my shoes, bike helmets, notebooks, and basically everything else I owned. I was going to school for engineering but also started shooting photos and videos of skiing. Right as I was starting to pick up momentum we had a really dry winter, where it just didn’t snow. So, I started drawing the ski photos I wished I was taking.

That led to a few years of balancing writing, shooting photos, and drawing skiing. Eventually, I nearly stopped taking photos, doing just one or two paid gigs a year, and instead started writing and drawing for NewSchoolers.com, a ski website. For several years, I wrote an article and drew a comic every week, all winter. That was great for forcing me to grow as an illustrator and keep the creativity flowing.

Even though I was working in the ski industry, I was still a mountain biker at heart. In middle school, I’d ride this one jump behind the grocery store over and over again for hours, and as soon as I got my driver’s license, I was up on Moscow Mountain all the time, pushing my downhill bike up for lap after lap of the two trails there. Opportunities kept opening in the ski industry, but I was always working behind the scenes to slide into the bike world professionally.

I made a big push for that in 2021, and in 2022, I went to the North American Enduro Cup as a racer, but between (slow) race stages, I painted the race and put together a fully illustrated race report for NSMB.com. That went over well, and I did my best to carry speed. Luckily, I’ve had many great illustration clients who kept bringing me work, and I was privileged to work with some of my favorite outlets. Now, I split my time between freelance illustration and working as the gear editor at Freehub magazine.

I really enjoy projects with personality. One of my favorite things is being able to crank out fun editorial illustrations at short notice. When I worked at Bike Mag, I loved getting a column in from a contributor or writing something myself and being able to draw something engaging to accompany it in a couple of hours. That’s the sort of work that caught my eye when I was young and made me want to be an illustrator.

On the other end of the spectrum, I’ve been lucky to do some huge projects recently. I painted two wallrides at Whistler for SRAM, and that got me all excited to do murals again. I also just wrapped up a series of 60 painted comics for NSMB and put together a book. That project has been fun because I put a few hours a week into it for nearly six months, and at the end, I had a bunch of work that hopefully folks enjoyed.

When I was getting into illustration, I loved Ryan Schmies and Adam Haynes. Ryan’s work for K2 was so evocative for me. All of his illustrations obviously had backstories and were just a little weird, a little off-kilter. Adam Haynes draws the tools we use to explore the mountains exactly how I see them. I love that precise linework and careful use of color combined with old trucks and machinery. When I saw his painting “Runnels” for the first time, I think I stood staring at it in the gallery for half an hour straight.

These days, my friends inspire me. We’ll go on a ride, joke around, and look at cool trees, and I’ll come home all excited to draw. My partner is a great sounding board. I’ll tell her a stupid idea, and she’ll tell me if it’s stupid, or suggest an alternate version that makes more sense, or just help me talk through it. She’s not a sycophant; we joke that people on Instagram like my work way more than she does, which is hugely helpful. If I lived with a yes-man, I’d be even more unbearable.

Back to that hilarious collection of part-time “dream jobs.” I’ve managed to make most of my passions my work. So I ride my bike a lot. I try to ride most days, but that’s “work” both because I’m getting time on review components for Freehub and because it’s refilling my creative tank. And then I love painting, but again, I can usually finagle it so that anytime I’ve got the brushes out, it’s “work.” Beyond that, I like building trails. I like reading. I like swimming in the creek by my house, but I don’t really have work/life balance. Instead, I have a lifestyle that lets me do the things I want to be doing pretty much all the time—and also pay rent. 

My relationship with bikes has had a massive impact on my life. I grew up in a Christian Nationalist cult, and folks from the mountain bike community were the first people outside that environment who showed me what my life could look like without that paradigm. Now, bikes serve as both a source of inspiration and a place to rest. When I’m overflowing with creative energy and need a place to put it, I’ll go on a ride and figure out what I want to make next. Similarly, when I’m drained and burnt out, I’ll go for a ride and turn off that part of my brain to let it rest.

This interview catches me at a funny time professionally. It’s June, which means I just finished up my big “first half of the year illustration project.” So, right now, I’ve got a bunch of pent-up creative energy, but I haven’t figured out where I want to put it. I want to do another big project, something with a multi-page comic element but also with more intricate painted stand-alone pieces. And I want it to be commercially viable; I want to work with brands to put this thing together.

Right now, we’re at this stage where I have a bike frame and a bunch of the components, but I haven’t assembled it yet because I’m trying to figure out what trail I want to ride with it. I’m sure I’ll have more direction soon, but for now, my future goals are mostly hard-to-articulate desires and vague aspirations. That’s fine, though, because berry season is starting up here. So I’m busy riding my bike, getting a little sick from eating too many berries, and swimming in the creek. 

The biggest thing I’ve learned on this unconventional career path is the power of aspirational but measured expectations. A few years ago, we bought a 20-year-old Subaru Baja, my dream car. And one of my wisest friends told me that it’s pretty easy to own your dream car and live your dream life when your goals for those dreams are attainable. If my dream car was a Ferrari, I’d be pretty frustrated because I’m nowhere near attaining that dream. But my dream car was cheap, I own it, and I’m living the dream!

I used to get frustrated because I’d set these lofty career goals for myself that I wasn’t able to complete, and worse, I had no idea what steps I’d even take to get there. And then I’d be frustrated when I fell short. Things began lining up better when I started saying, “Well, what can I do that will be hard, that will be a stretch, that will push me, but that I’m very confident I can accomplish?” Consistently setting attainable but challenging goals sets me up better to quantify the hard work it will take to accomplish them. It gives me something to grind toward, something to hustle to achieve, instead of something unattainable that I’d have to just magically have great talent to do.

I’m not a very talented person. I don’t have some well of creativity that I can express effortlessly. Often I feel like I’m struggling up the climbs while other folks are spinning away without breaking a sweat. But when I can tell myself to hustle to the next switchback because I can see it, and from there, I’ll be able to see the next one, it all makes more sense.

Cy’s Illustration Tools

I use a mix of traditional and digital tools. Most drawings start as physical sketches, and then I finalize line work in Procreate on the iPad. Then I either color digitally or print on watercolor paper and use gouache paints or alcohol ink markers to color. When I’m painting in the field, I use a Winsor & Newton watercolor set that my friend got in high school and never used. I carry it with a custom-made clipboard in a zippered pouch that fits in a hip pack.

Featured Illustration

I drew the piece below back in 2020. When the pandemic hit, I lost basically all my freelance work. So I’d just go dig at the local dirt jumps all morning, and in the afternoons, I taught myself how to use gouache paint. For around 120 days, I did a small gouache painting every day, and then I’d sell them on Instagram with a “pay what you want” model. I called it “Paintings to Poop to” because they were a good size to hang in your bathroom, and I was just trying to put a little bit of joy into a pretty depressing time.

This piece aims to capture one of my favorite feelings while bikepacking. Ride all day, retreat to the tent at night, and go to sleep content because all you’ve got to do the next day is ride your bike again. My partner is great at putting together ambitious bikepacking routes that may or may not involve a lot of hike-a-bike, and I love traveling efficiently with her, just spinning the pedals all day, eating ramen, and sleeping so hard.

You can find more from Cy at About-Ride.com and on Instagram.

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