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


The Drawing Megachallenge #2: The Challenges

Following the idea of the 30-day drawing challenges, I made up 10 subject lists of 30 items each (10 “sets”), so that each will take you about a month to complete, if you do a drawing-a-day.

The 10 “sets”:

  1. Objects (everyday objects you can easily copy, plus a couple of fantasy ones)
  2. Human figure, performing specific poses or actions. Every human figure list is divided, 15 male and 15 female, so I have to practice both
  3. Human faces, practicing different expressions and different hair styles
  4. Human figure, now specifying “non-fantastic” roles and professions. Here the goal is to observe more carefully clothing, accessories, manipulating items…
  5. Animals
  6. Human figure, fantastic, historical of sci-fi types
  7. Fantastic beasts and monsters
  8. Vehicles (real and fantastic)
  9. Buildings
  10. Scenery

10 sets means about 300 drawing “challenges” or ideas, grouped by topics and building up towards increasing complexity and difficulty. (There is a sci-fi/fantasy theme in some of the lists, which you can skip over if that is not your thing). Already I am finding the need for some “supplemental” lists, that I will list here as the need for them grows.

Supplemental set 1 (Set 11): Hands

This is a big project. I’m only a few challenges in, so I’ll probably be changing many things as I go. I can’t, obviously, guarantee results; but I can tell you that I have personally learned a LOT just by trying to draw things that I hadn’t tried before.

Since I want to start with the basics (pencil sketches) and incorporate more advanced techniques all the way to digital painting, and hopefully develop something of my own style on the way, I’ve combined these sets with a list of 8 “techniques.” More on these in future posts. This is the list:

The 8 techniques:   (These will be explained further in a new post)

1. Pencil studies: rough sketches of any kind; the goal is to investigate the “inner structure” of your objects.
2. Clean lines (or “line art”): sketches are fun, but now push yourself to finish a drawing!
3. 2-D simplified sketches (like old clipart or signs).
4. Digital line art, going from sketches to cleaned lines but on your computer or tablet. The goal is to become familiar with basic tools of digital drawing (tablet, program, brushes…)
5. Digital doodling. Very basic/abstract, quick representations.
6. Basic digital coloring. Begin exploring tools for coloring. The focus is on learning how to use the tools and exploring palettes, rather than on getting the details (shading, lighting) “right.”
7. 2-D design (traditional or digital), Another foray into the abstract, but here looking more intentionally for a “logo” look.
8. Advanced digital coloring.

For the complete sets (a.k.a. “Challenges”) just expand this post!

Click to see the full Challenges!

The Drawing Megachallenge #3: The “Rules”

If you want to try the Path of the Megachallenge, little pencilhopper, here are some, erm, “rules” that can be helpful:

Rule 1: All these rules are suggestions!

This is not a do or die method! It’s just to help me (and whomever wants to try it) on the way! Feel free to skip topics, mix them, change the order of lists or styles, move to a different list if you feel you’ve done too much of the same and then come back, switch male and female topics, or whatever. Exercise your freedom!

Rule 2: Push yourself!

Try to do one challenge a day, and try to follow the list to some extent. Otherwise you may end up just drawing those challenges you are comfortable with (and then you’ll be learning very little). Even if out of order, try to finish one set before moving to the next. It is difficult, but soon you’ll find it is fun to try drawing something difficult, and figuring it out!

Rule 3: Don’t judge your drawings! Draw-and-forget, keep moving forward.

This is perhaps the most important rule.

I took a drawing class recently. After working for about an hour, our teacher ordered us to rip our first drawings to pieces and throw them to the garbage!

03-21-Medium-length, unkempt. Surprised.

I was going for 03-21=surprised. I think it looks more like scared. So that would be mmm… 03-07.

At the moment I thought it was cruel, but there is great wisdom to this approach: I was already judging, by our first warm-up exercise, my own worth as an artist! And doing quite poorly. Instead, this draw-and-discard approach was liberating! It made you realize that each drawing, good or bad, is a step towards greater skill, and that mistakes are as useful to learning as hitting the nail on the head. This is as important with the pencil sketches as with the most advanced techniques.

On a more personal note, this is why I decided to post my own middling works. There’s so much incredibly cool art on the internet, that beginners such as me can (and do) easily get discouraged. By posting my own beginning steps (unimpressive to anyone else, but to me, filled with that surprise that comes when a drawing turns out better than your previous ones), other middling amateurs will find encouragement and keep learning!

Rule 4: Test your own resources first, use references later

I’m not sure if this is a good rule; I’m kind of testing it out.

My approach is to try to discover things on my own first. See how much I can draw from memory, then look for a real model (e.g. my own pose in the mirror, an actual car or cat or policeman), then look for online pictures and references, and then, as a fourth step, for tutorials and online tips & tricks. I think one learns better this way. Tutorials can be excellent for completing the work, solving that problem that drives you crazy, but can be very limiting if you start there – you’d be copying someone else’s style.

Something I learned already from this rule, by the way, is how little I do actually observe! I don’t even know what a rock singer wears!

But then you learn this little trick, though: close your eyes, and concentrate on trying to remember those details. You’ve seen those things; perhaps you are not paying attention to your own memories! Following this rule will train you to observe and remember.

Rule 5: Whenever possible, copy from real

One thing that my teacher (from rule #3) insisted on was to learn by copying from real, 3-D objects, as opposed to from pictures (even from pictures of those same 3-D objects). His argument was that when we draw we are flattening the object; if we copy from a picture we are flattening even more something already flattened—shadows of shadows, as Plato would have it. I don’t know exactly why, but this shows in my drawings: the lines don’t go the same way; my drawings from “reference” pictures look wrong.

Of course this may become a bit problematic when you’re trying to draw, say, a leaping werewolf; but my guess is that the preliminary, non-fantasy subjects can help you develop enough of an eye to compensate later, when drawing from one’s imagination. (And also, remember rule #1.)

Rule 6: References are good shortcuts

And by “references” I mean anything that you can observe and copy from, even tutorials and tips. What, this contradicts my two previous rules??? Gall dang, yes! I think there’s a point where you find you can’t quite make much more progress on your own, and that’s the time to launch Pinterest or your favorite source, and see how others do it.

When? You’ll know. Let your hunger guide you to the right food. Don’t stuff yourself up with charts and tutorials and references for which you have yet no use (or that may spoil your appetite for the real thing).

Rule 7: Carry a pencil in your pocket

I keep a regular 2B, with a pen cap held in place with a rubber band so it doesn’t lose its point. Primitive, yeah, but when a lecture gets boring, or the waiting gets long, it’s a much better option than wasting time on my phone! There’ll always be something I can sketch (but in case I only get the back of a dozen heads, I also bring with me the current list I’m working on).

I think I’ll start looking for a pocket-sized notebook too, one with a sleeve for a pencil, for when I can’t carry around a regular-sized one.

Rule 8: Share!

Add notes to your drawings – what you liked, what you discovered – and tag them accordingly for others to find and get inspired!

More on sharing in my next post…