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Push Yourself

We recently asked Jessie Young, an illustrator, teacher, and “professional nerd,” to tell us about her self-initiated project of drawing 100 vector portraits. Here’s what she had to say.

The series started because I wanted my students to know that I could walk the walk. In addition to making my own work, I teach digital art and animation to high school students at Cambridge Rindge and Latin School during the school year and drawing with more traditional materials at the Putney School Summer Programs during the summer. I like to think that my sparkling personality and my impressive teacher voice form an awesome fighting force to earn and keep their respect, but I just wouldn't feel right if I couldn't do the same challenges that I ask of them. That's why I started this series—I wanted to prove to my year-long kids that their homework was challenging, but doable, and I wanted to show my summer students that I'd take a crack at doing their independent project, too.

The series is half "art pushups" and half "100 drawings challenge." I give my advanced digital studio students weekly self-directed homework so they can turn their weaknesses into strengths through relentless, structured hard work, much like how pushups build muscles. If a student has a hard time drawing, say, hands, they commit to drawing 10 hands a week for the marking period until they have a giant pile of drawings, and then we look at how far they've come by examining the entire collection. In my case, I don't work very quickly (well, didn't) so I decided that I wanted to fix that by doing a series of quick portraits that I'd work on every day. Goal-wise, I needed something more concrete than just "lots and lots." I looked to the independent projects that some of my bolder Putney students try and thought, "Why not a hundred?" So I art-pushupped my way through my days starting with day one of the marking period, and kept the goal of drawing a hundred portraits as a way to stay focused and keep myself from slacking.

My process for these is simple. I just look at someone and I draw them. No filters, no tracing. I use an iPad Pro and Apple Pencil so I can work wherever I like, and Adobe Illustrator Draw is my preferred program for about 80 to 90% of the process.

I start with lines, and once I have that as a structure, I go from opposite ends of a grayscale in layers and work my way to the middle. Then I throw some pops of color into the background (and sometimes the foreground) and I send it to Adobe Illustrator CC to clean it up and add finishing touches, like gradients and such. Pretty straightforward.

I'm only about a third of the way into it, but I'm already seeing a massive change to the way I work. For one, it's made me far more quick and relaxed when it comes to observational drawing. I'm obsessively detail-oriented. I draw every single tiny little thing, but forcing myself to work quickly has helped me learn to bypass the details that no one else cares about. Also, the speed has made my marks cleaner, smoother, and more forceful in a way that I really love. However, this progress has only come from a fairly brutal culling of my bad habits. It's been hard to make myself change my routines, much like how going back to the gym leaves you with body aches from using muscles you haven't exercised in that way for so long.

That's where the drawing I call "Push Yourself, but Know Your Limits" [left] came from—the soreness. I was in a rut again and I was really tired. I had just forced myself to draw one more damned portrait and I wasn't looking forward to doing the next one, even though I knew that I had to if I was going to stick to my plan. I had hit a wall where I had gotten too comfortable doing the same things and the portraits were getting formulaic. 

I knew that I needed to power through to make changes so I could keep getting better, but it was so hard to keep examining my bad habits and working through them one by one. I wanted to show some of what I was personally feeling about the whole process. I think I got there. I suppose it's for the viewer to judge.