This is what I do

Self-portrait sketches by Chandler O'Leary

My name is Chandler O’Leary. I graduated with a degree in illustration from RISD (Rhode Island School of Design), and run a small business as an illustrator and lettering artist. I live in Washington state with my lovely husband (whom I refer to as “the Tailor” because he makes his own clothes and wishes to remain anonymous) and our tiny stick-shift Subaru sedan. We both love to travel, but I’m the real nut in the family. For one thing, I have lived all over the U.S. and even in Italy—so the urge to wander is deeply ingrained. And I am the one who will choose the squiggliest line on the map, rather than the Interstate highway, every single time. I am the one who gets excited about driving 200 miles out of my way to see a giant concrete prairie dog. I am the one who will add an extra day to our trip to make sure we have enough time to spend at Wall Drug. I also have a thing for jackalopes, I brake for any coffee-pot-shaped building, and I have a bright yellow hat shaped like cartoon Swiss cheese.

I’ve been recording my travels in my sketchbooks for over 20 years. One day I realized I had literally hundreds of drawings hidden away, and only a few close friends had ever seen them all. Since I draw pictures all day for a living, it’s not like I don’t have a creative outlet. But somehow my travel sketches just didn’t…fit…with the story I had been weaving through my other work. So thanks to some gentle prodding from my friend Mary-Alice, I finally decided it was time to start the next chapter.

The majority of the posts on this site deal with road trips, because that’s my favorite way to travel. But there are also plane trips, and boat trips, and train trips, and other trips, too. None of this is posted here in real time, though. I prefer to post my sketches thematically, rather than chronologically. So if you keep up with this blog, you’ll find posts jumping around from place to place, and back and forth in time. (Look for the “sketched on” date stamp at the bottom of each post, if you’re curious.) That way I can tell a larger or deeper travel story than simply “On day four we went here, and then we did this, and then I saw this…”

Process materials sketch by Chandler O'Leary

I get almost daily emails and questions about my process and the materials I use, so above is a little sketch I put together of my supply kit. Below is a brief overview of my process; for a full, exhaustive list of all the tools and supplies I use, visit my FAQ.

I use a variety of sketchbook types, but lately my go-to is the ubiquitous Moleskine. It’s hardly the perfect sketchbook, but it’s a handy size for traveling, and its el-cheapo-quality paper keeps me from getting too precious with my drawings. That paper is also generally terrible for watercolor, so if you’re a beginning sketchbook artist, beware. I just happen to like that blotchy-bleedy effect—the lack of control makes for some nicely surprising results.

In my pack at all times are at least one sketchbook, a handful of pens, a small watercolor box, a container of water, and a big ol’ squirrel mop brush (which allows for both big washes and tiny details without switching brushes). There’s also a pencil in there, just in case, but I primarily draw straight-up in black pen. That way, I have to live with whatever mistakes I make (you’ll see some crossing out on this site!), and not worry so much about perfection. Embracing imperfection also keeps me trained to work fast—a handy skill when you’re sketching on the road.

Camera and car sketch by Chandler O'Leary

You’ll notice there are no photographs on this site (I saved those for my Instagram account). The reason for that is the same reason why I choose to document my travels through drawing. I’ve found that picking the sketchbook over the camera forces me to really look at what I see before me. I might not get to every single landmark by choosing the slow road this way, but my memories of my travels are crystal-clear, even many years later. This way, I’m relying on my eye, rather than the lens, to do all the seeing: what I lose in breadth I gain in depth.

That said, time is not unlimited—racing the clock is an occupational hazard of travel sketching. If I had superpowers, I’d just stop time, plonk myself down, and spend as many hours as it takes to draw everything that suits my fancy. But the reality is often that I have somewhere to be in an hour, or another hundred miles to drive before dark, or travel companions who are waiting for me to catch up. Or I’m in a not-so-great neighborhood, or it’s pouring rain, or it’s below freezing and my hand feels like it’s going to fall off. So I also carry a camera with me on my travels—usually my trusty Canon 7D, although my phone works in a pinch—in case I need to fill in the gaps or add color later.

Sketching in the passenger seat (illustration by Chandler O'Leary)

Most of my drawings were done on-location, at least in part (see above). A few, though, were done from memory, or with the aid of my photographs, sometimes well after-the-fact. And I love to take artistic license with what I see—like when I sketch “shotgun” while my husband drives—jotting down the flavor of a place rather than every literal detail. The common denominator, though, is that everything I document here is something I have actually experienced myself. These are all places I’ve actually been, sights I’ve actually seen, meals I’ve actually tasted, roads I’ve actually driven. So rather than a faithful documentary journal of every personal experience, I like to think of this site as an illustrated travel guide.

Did I miss anything? Still have questions? You’ll find tons more answers in my FAQ.

I’m always looking for new places, interesting landmarks, and crazy roadside attractions to draw. I’m interested in nearly everything, but I’m a real sucker for giant fiberglass animals, local secrets, breathtaking panoramas, roadside randomness, and hidden back roads. So if you have any recommendations or stories to pass along, please share! (Though I should tell you, in the interest of full disclosure: This page and my FAQ contain links to Amazon, from whom I receive a small commission via their affiliate program. I don’t accept sponsored posts or travel, guest content or any other form of advertising. I get many, many requests from advertisers and companies looking for sponsored content, and I turn them all down. I pay for my own travel and materials, and I will not create sketches or blog posts to support any company or brand. All of my trip itineraries, content and opinions are my own. I do, however, take professional illustration commissions and some of my sketchbook drawings are available for licensing; for client and licensing inquiries, feel free to contact me.) My Facebook page is a repository for travel ephemera, process shots, souvenir photos and shared stories. And of course, you can always leave a comment here on the blog or Tweet at me anytime.

So don’t be shy! Let’s see what’s beyond that next bend in the road—together.



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