evin Tudball always gets a few new followers on instagram this time of year - he’s known for his Drawlloween series of fun, illustrated creatures and ghouls. It’s a time of year where his imagination can run wild. And people have noticed.

But Kevin doesn’t just use his imagination during the spooky season. Based in Portland, Oregon, Kevin is an illustration-forward art director, working with the likes of the Washington Post, the Speciality Coffee Association, Google, Netflix, and most recently, REI. 

For over 6 years, Kevin has run his own studio, working on all sorts of wildly fun illustration, branding, and packaging projects. When Kevin's wife starting her job as a traveling nurse in 2018, they both started traveling from city to city. And that’s where he learned an entirely new set of tricks to the trade while on-the-road. 

We caught up with Kevin to hear his story and learn about how he adapted to working remotely on his projects without a home-base.

Q: When did you start working on the road? And why?

Kevin: In 2018 my wife got a job as a Travel Nurse and we started living on the road. We spent the next 2 years, right up until the pandemic, living in 5 different cities across the country.

Q: How do you typically set up design proposals with your clients? Did that change at all while working “on the road”?

Kevin: My clients have always been in multiple states and countries, so my relationships with my clients didn’t change very much. I usually organize my proposals, contracts, and invoices using online tools, such as Basil.

Q: When you were working while traveling, what did your clients think about your nomadic lifestyle?

Kevin: Most of my clients found my nomadic lifestyle inspiring and interesting! It always gave us something interesting to talk about and catch up on. The downside for my clients was that my timezone changed every few months, so setting up meetings could be tricky. Most of my clients at that time preferred to pay by check, so my address always changing wasn’t a favorite for payroll.

Q: What cities did you travel to and which was your favorite to work in?

Kevin: Over the course of 2 years we lived in Santa Cruz (CA), New Haven (CT), Portland (OR), San Diego (CA), Ann Arbor (MI), and Austin (TX). We returned to Portland at the end and bought a home there. Objectively Portland had the most to offer both of our careers and is a very fun city to live. The art and design culture here is very strong, and there are a lot of creative jobs. That said, San Diego was probably the most fun place to work. We were living in Airbnb’s, so we had a great sunny patio, with an ocean breeze that I could work on. It’s hard to beat that!

Q: Were there any awkward/stressful moments while working on-the-road?

Kevin: The most awkward and stressful moments were tracking down checks. With small clients it’s easy to just remind them that I was moving a lot. With bigger clients, however, their payroll departments don’t operate on that personal level. There were a few times I had to have companies recut and cancel checks, because they ended up in the wrong city at an old address. Now that there are services like Basil, I have the ability to accept credit card payments and do bank transfers, so that problem has been solved.

Q: Tell us about a favorite project or two during that time.

Kevin: The most exciting project I had during this time was my first editorial illustration for The Washington Post. They contacted me 2 weeks before I was set to move from Austin to Portland, so I had to be very efficient with my time, but I was also so excited that it wasn’t hard to put my focus into the project. Luckily the news cycle also moves fast, so I was able to present them with preliminary sketches and complete the final graphic before the move. 

Another project I fell in love with during this time was Drawlloween. This is a personal passion project, but every October illustrators all over the world participate in this social-media based art project. There are many variations on Drawlloween, but the idea is everyday you create a piece of art based on a prompt that’s been provided. While I was on the road this was a very notable activity because it connected me to other illustrators, designers, and artists all over the world. It’s hard to find community while living on the road, so social-media ended up being a very important way to stay connected.

Q: Did traveling make anything harder/more complicated as a freelancer?

Kevin: Outside of dealing with my changing time zones and addresses, the hardest part of traveling was having a solid work station. At the time we started traveling I was used to having a printer, scanner, art supplies, a huge 24” Wacom Cintiq, an iPad Pro and my Macbook Pro. I ditched the printer, scanner and art supplies and went fully digital at that point. That was a huge learning curve, but it did force me to get better at digital art. 

I also had to adapt to different office setups in each city. In New Haven I worked at a co-work space, in Portland and San Diego I had to get setup at the kitchen table, and in Ann Arbor and Austin I bought used desks and resold them when I moved. Each had it’s own advantages, but there is something to be said for having a home base and work station that you’ve really customized to your needs. That said, if I were to do it all again, I would probably just use a Macbook Pro and an iPad Pro and keep things simple.

Q: What was the most surprising thing you learned or changed while working on the road?

Kevin: Forcing myself to learn digital illustration tools allowed me to speed up my workflow and gave me the ability take on bigger projects. I was surprised how quickly my iPad Pro became my primary work tool. While I enjoy building graphics from hand-drawn illustrations, using pens and paint, my iPad allowed me to make edits much faster. While this might not seem that notable, it made traveling much more possible. For example, we drove across the country 4 times, and while on the road in the middle of the country, I could get an e-mail with edits, pull over the car, make the edits on my iPad and get them back to a client that same day, without losing work. That helped show my clients that my traveling would not be an issue and allowed me to live a lifestyle I’d always dreamed of.


Kevin is currently working on a long-term contract with REI and doing amazing work like this Boston-based mural:

Check out more of his work here.

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