Drawing Hack: How to Motivate Yourself + Improve Your Drawing Abilities

When I was a kid, my brothers and I used to sit on the living room floor playing an exceptionally elaborate game called “What should I draw?” One of us would ask, “What should I draw?” Someone would answer, “a bear.” Then you would draw a bear.

Polar Bear letterpress print

My art education evolved as I grew, but at essence, a formal art education consists of more and more elaborate versions of “What should I draw?” At the end of it all, I made my way out into the world, and without the structure of school or a group of peers egging me on, I wasn’t quite sure what to do with myself.

So I made it up. I started Cloudy Collection in 2009 as a way to give myself something to make every three months. I picked a topic and two colors and asked some friends to play along, and we would have the images made into letterpress prints. For three years, I kept a strict publishing schedule. By the end of the project in 2011, we had 100 prints made by 80 different artists. Plus I had a much-improved portfolio and a bunch more friends who were also illustrators, designers, and other smart and talented artists.

I didn’t realize it at the time, but I had created a self-assignment. I am now aware of many wonderful self-assignments out there, and the best ones have structure, generating clear benefits.

Here’s how to start making your own assignments to improve your drawing abilities:

1) Pick a topic.

Interloper letterpress print

I’ve already tried to convince you that the only way to get better at drawing is that you need to draw more. But what, exactly, should you draw? Anything. There are no rules. You probably know better than anyone what it is you need or want to get better at drawing. Sure, I could suggest something, or better yet point you to my friend Phil McAndrew’s amazing list of 200 suggestions. But whatever you choose, make sure it is something you are willing to stick with for a while.

For me, with Cloudy Collection, I wanted to practice working with a limited color palette, I wanted to experiment with different media and I wanted to create a design system that could tie all the disparate art together, regardless of the diversity of all the art included. I set up the structure of the project to touch on these key topics and to catch a few side benefits along the way. That structure was important to the project’s success because in making some rules for myself upfront, I was free to explore within the constraints without having to make all those decisions each time I sat down to work.

When you set up a self-assignment, you are setting yourself up to push past the easy, low-hanging-fruit types of ideas and skills. The goal is to keep going until you are the master of the assignment, and then go just a little while longer until you get even better.

When you stick with the same topic long enough, you are forced to explore all options. Once you are really good at drawing an ear, how many different ways can you color an ear? Or now that you’ve got human ears perfected, what does an elephant’s ear look like? Can you create the ears with cut paper instead of pen and ink? Who have the smallest ears? The best hearing? When all the obvious options are exhausted, things get interesting (or just strange, which can be interesting!): What about dog-eared pages in a book? Where are a cricket’s ears? Does an ear of corn count?

Go down that rabbit hole, take some risks, and make something you’ve never made before.

2) Keep a schedule.

The key to a successful self-assignment is to keep at it, all the way to the end. There is a wonderful anecdote from comedian Jerry Seinfeld about how he keeps himself motivated. Essentially, he puts a big wall calendar up where he does his writing, and each day that he works on his routine, he puts a big red X over that day on the calendar. The act of X-ing out each day is not only satisfying, but it creates a visual “chain” of those red X’s. Seinfeld warns you not to disappoint yourself: “Don’t break that chain!”

I can be incredibly undisciplined without a deadline hanging over me. The trick I’ve found to create the illusion of discipline is to trick myself into thinking I have no other choice than to get the work done. With Cloudy Collection, I had to get art collected from six other artists and myself, coordinate with the printer, and then package the sets of prints and ship them out. Every three months, it was the same thing, and by involving those other artists and the printer, I was making a promise to them and to myself that I would get it all done on time.

If you can get work done without tricking yourself into it, more power to you. But for the rest of us, creating real or imagined deadlines can be a strong motivator. And to force yourself to push past that first time (and second, third, fiftieth time) you lose enthusiasm, set up a ridiculously high target — do it every day for a month. Or a year!

3) Share what you’ve made.

Monster Parade Dragon screen print

This may be the most important component to a successful self-assignment. Once you make all this work, you need to make it public. In this, the Internet age, there is no excuse for not putting your work out in some public way. Getting your own domain name is nice, but a free Tumblr blog will do the trick just as well. But if you are truly interested in getting better, and especially if you are interested in making illustrations professionally, you need to share what you’ve made. Nobody can hire you if they don’t know about you and the work you make.


Making Cloudy Collection, it was always intended to be public. I wanted to share the work of some of my favorite artists with the rest of the world. In the process, I also got my own work out in the world, and the very first print I made for the project was directly responsible for catching the eye of my editor for the first children’s book I illustrated.

Beyond getting noticed, sharing your work is a way to find a community of other artists and like-minded people. It is a way for you to feel connected to the wider world, even though you probably spend a lot of your time drawing in a room by yourself. The more you share of your work, the more others share their work with you. Outside of a formal school structure, this kind of community is incredibly rare and valuable.

And here’s an open secret: sharing what you’ve learned is one of your best opportunities to learn. Every time I teach someone else about something that I’ve learned or taught myself, I have to figure out clearest way to explain it. In that process of “coming to terms” with a topic (literally, finding the right words), I more clearly comprehend what I’ve been unconsciously reaching for all along.

A self-assignment doesn’t have to be a daunting, monumental concept that locks you up before you pick up your pencil. On the contrary, the best ones I know of are simple ideas that just give the artist somewhere to start each time they sit down at the drawing table.

Simple letterpress print

So why not think of something simple to do the next time you get out your pencils? Then set some deadlines for yourself and start posting!

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