How to Motivate Yourself, Improve Your Drawing Skills and (Very Important!) Share Your Work With the World

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When I was a kid, I'd play a game called "What should I draw?" Someone would ask, "What should I draw?" Someone would answer, "A bear." Then you would draw a bear. Pretty basic, right?

My formal art education consisted of increasingly challenging versions of "What should I draw?" But when I made my way out into the world, I wasn't quite sure how to move forward without the structure of classes or a group of peers egging me on.

So I made something up! I started Cloudy Collection in 2009 as a way to give myself deadlines. I picked a topic and two colors and asked some friends to play along. 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.

I didn't realize it at the time, but I had created a self-assignment, a way of holding myself accountable and making art. The best assignments have structure and generate clear benefits. Here's how to do this for yourself.

1. Pick a Topic

The key here is to establish a self-assignment that pushes you 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? What animals 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? Does an ear of corn count?

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!"

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 Your Work

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This may be the most important component to a successful self-assignment. If you are truly interested in getting better, and especially if you want to draw illustrations professionally, you need to share your work. Getting your own domain name is nice, but a free Tumblr blog or Instagram account will do the job just as well.

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 others, even though you probably spend a lot of your time drawing in a room by yourself. The more you share, the more others share with you. This is all 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 the 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.

4. Don't Overthink It

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

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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