All of us doodled things in school. Many of us might have felt discouraged when some other kid drew better than us. This early trauma leads us to think that drawing needs talent, or artistic sensibility. This is not entirely true. The most important thing is to understand the mechanisms involved in the action of drawing in order to use them properly. These mechanisms are really simple and are mostly easy to handle.
Observational Drawing - It's all in the Eyes and Hands
To draw the face of somebody you know, you must draw what you see, not what your memory tells you. Your brain can be considered as a vast clip art databank, and it might prefer to use those images instead of the actual shapes you are observing. Practice drawing shapes by drawing your hand (preferably the one which isn't holding the pencil) while carefully avoiding looking at what you are drawing. Repeat until you are able to associate the movement of your eyes on the shape of your free hand and fingers to the movement of the pencil. In order to make a faithful drawing of an existing object, you must analyse its shape. Place your fully-extended arm in front of your face, palm down, elbow besides your nose, and look at your hand. It looks like nothing, just a lumpy and rather weird piece of flesh. Drawing it is tricky, because your brain constantly tries to replace what you see with its image of a recognisable body part; it thinks it knows better than your eyes. It will constantly step into the process, showing you images of good-looking, well-posed hands it remembers, waving them at your mind. Copying upside-down images is a good way to trick your brain into not having time to make up another image, and force you to look at the real shape.
Successful portraying is difficult, and depends on how well you manage to fight the succession of clip art images battling to get in front of your eyes. The best way to avoid them is to begin with vague, fuzzy lines then progressively sharpen and darken them, slowly spreading details. The counter-example of this is the usual way we draw a face, beginning with highly detailed eyes and mouth from our mental clip art gallery, and then trying to figure out the rest of the head.
Succeeding in the representation of perspective and shapes is a matter of observation. This can only be achieved with practice. Drawing better means drawing more. It is a wonderful way to pass time, impress friends or even make money. Always take a small drawing pad and pencil when you go out, and occupy any free time (for example, when waiting for a bus) by drawing your surroundings.
Books on drawing can't hurt, even cheap ones. A visual thesaurus can be helpful when dealing with odd or complex objects. Drawings done by professionals can be a source of inspiration - just be careful not to copy them. We are talking observation drawing here, so always rely on the reality you see instead of that seen by others.
The deliberate repetition of a mistake can lead to the creation of a style. Observational and true-to-life representations are hard to achieve and may seem to offer limited expression possibilities. There's nothing stopping you saying 'screw it' to it all and drawing your own way! The main idea here is self-confidence. You must believe that nothing you draw is wrong. The best way to progress is to experiment.
Experimenting with Media
Try doing the same simple drawing with everything you can lay your hands on: crayons, pens, pencils, ink, finger painting, acrylic paint, ash, salt and glue, torn paper, etc. Combine two or more of these on a variety of surfaces: paper, carton, glass, wood, bark, tables, floors and walls for further inspiration.
Consider the feeling that every medium brings. The way they are used can affect the feeling. Hard-pressed violently applied crayon does not suggest the same state of mind as one gently and carefully used.
One mistake every beginner makes is to use outlines by default. This comes from all those colouring books we looked at for too long as children. Consider not using outlines: try using oversized outlines; try using only spots, or crosshatches; try using fingerprints, or potato prints. Documentation here can become very useful, as it supplies starting points to experiment with new styles. Image banks are a good place to find some original illustrations, but inspiration can come from anywhere. It's a matter of finding what can be useful by trying everything and progressively narrowing down to what gives interesting output. Never throw away anything you draw. Ever. Unless you have a really good reason to do so1. Every piece of art you produce can have a bit of originality in it, which you could develop or exploit later.
Combining the Two
After a while, if you begin to master drawing from models, and have experimented your way through the process of stylisation, you are ready for a new challenge: combining reality and your artistic view. A good way to begin is to make stylish versions of your earlier observation drawings by tracing them2 or just drawing on them with another medium such as water and ink.
Keeping Those Masterpieces
Keep everything in a portfolio you can easily browse, like a scrapbook. Take notes. If your creative impulse resulted in oversized pictures, make yourself a large envelope out of thick paperboard. If you plan to use charcoal or soft pencils, consider buying a coating spray to avoid smudging. Date your artwork.
If you ever become bored, keep them in a place you can forget about. You will be amazingly surprised to find them again one day, and it may push you back onto the track of creativity. Just be confident, as the only bad artist is the artist who doesn't enjoy creating. If you like it, the odds are that some other people will. If not, persevere and ask for constructive criticism, or frown and become a misunderstood artist. Either way, have fun!