The Drawing Megachallenge #1: The Whys

The main challenge when learning to draw, in my experience, is that, until you actually become very good, everything you draw looks rather cruddy. That’s why most of us stop drawing for pleasure around age ten or so: by then our inner critic has grown too clever for our own good. None of our art looks like the cool stuff we see around us, and we are not experienced enough to realize that the only way to climb that curve is by making lots and lots of rather cruddy drawings.

So we give up on art.

I did not quite give up at that age, but did not go much farther either. Whenever I got the itch to draw, I’d fall back on the four things I’d learned to draw by copying other drawings. These were, in no particular order:

  • a black bird
  • a flying eagle
  • a dragon (from the neck up; I still can’t figure out the legs)
  • a knight holding a big sword, ready to fight the dragon. He looks a bit dumb if I don’t draw the dragon.

Bird and knight-b-001

That’s about it. Every time I tried to draw something else I’d ended up throwing my experiment away, frustrated, and drawing one of those four things. It’s kind of like St. Exupery tells in The Little Prince, how he only knew how to draw a boa (it looked like a spaghetti with eyes), or alternatively, a boa that swallowed an elephant (it looked suspiciously like a hat). So when the Little Prince asked him to draw a rose, he just drew the boa.


I had to draw my own boa. I don’t want a lawsuit from St. Exupery.

Hmm. I think I could add the boa to my list.

Recently I got the bug again and took a drawing class at the place where I teach (philosophy, not art. Just to be clear). Looking for ways to motivate myself to keep practicing (and practice is the only way you can get good at drawing!) I discovered on Pinterest the “30-day drawing challenges.” There’s a whole bunch of them. I thought, of course, What a great idea! I’ll keep these in a place where I can see them, and after a few months my drawing skills will get so much better!

The trouble, I soon found out, is this: most of those drawing challenges don’t have any kind of progression, any structure to guide you into, say, developing basic skills, and then building up from them. They mostly look something like this:

30-day Drawing Challenge
Day 1 Draw an animal
Day 2 Draw your favorite Disney character
Day 3 Draw a monster or mythical creature
Day 4 Draw a shopping cart looking at his watch
Day 5 Draw a wedding cake with a Disney character figurine on it
Day 6 Draw a Halloween version of your favorite Disney character. (Disney characters seem to be very popular in these challenges).
Day 7… Etc. etc.

Which is fine, if you already know how to draw! But given my limitations, my challenge would probably look something like this:

My 30-day Drawing Challenge
Day 1: Draw an animal.
Here’s my boa. It’s coming handy already. Actually there’s two animals there, since he’s eaten the elephant. I’m rocking this challenge.
Day 2: Draw your favorite Disney character.
Easy: that would be the dragon from Sleeping Beauty.
Day 3: Draw a monster or mythical creature.
Well, a dragon is a monster…
Day 4: Draw a shopping cart looking at his watch.
Now I got stumped. How do I go from a dragon’s head to this?



(I guess I should be thankful. Day five was going to look like I decapitated a dragon and served the head in the wedding. Gross.)

There’s another problem too: Unless you are a developed artist already, these prompts will not help you develop a style. Think about this: if you practice by copying a Disney character, you are basically learning to draw how someone drew that Disney character!

What I wanted – and what I’m trying to develop here, and maybe share with the world – is a structure that would put me on the path to:

(a) Develop the basic skills you need to start drawing: observation, copying from real models, pencil-eye coordination and so forth.

(b) Discover the basic structure of the objects I want to draw, so I can play with them and modify them at will. Get that knight to put down his sword and dance, if he wants to.

(c) Build up a “mental library” of the details that make such drawings lifelike.

(d) Progress from basic techniques to more complex ones (say, from pencil sketches to digital painting…)

(e) Develop a style (or styles) of my own, something that makes my art mine, distinctive.

That’s the why of this Drawing Megachallenge. It is simply a list (or a series of 30-object lists) of things to draw, that tries to build progressively from the more basic to the more complex, from copying to imagining, from sketching to more involved techniques.

I ended up with 10 sets (call it 10 basic challenges, if you will) of 30 objects each, which you can draw one-a-day if you want to focus on a set per month. But you can use them many times in order to learn different techniques. They can be combined, too, and mixed up for additional challenges.

In my next post I’ll talk about the lists — the “challenges.”

Next>>> See #2: The Challenges


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