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I try to keep a sketchbook going most of the time; I use it for roughs for most every art project I do, for practice in drawing, for doodling and fun. Over the long term it ends up creating a montage of what's going on in my life at any one time.
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Heads are such fun to draw, yet they're probably the most frustrating and humiliating artistic subjects anyone could choose to attempt. Trying to capture a likeness from a living, moving model can be just about the most humbling artistic experience anyone could choose. Not only are you trying to get the image down quickly on paper with a moving subject, but there's incredible pressure to actually make it _look_ like the person, as they impatiently wait to see what wonders you've drawn. No pressure.

There are a few tricks that you can use, though. One of the main ones I rely on is to go into an analytical mode of thinking and drawing, where you reduce the person you're drawing down into a collection of shapes. This has to happen first in your mind, then it can flow out onto the paper. You start first with the largest overall shapes, and only after you have the head laid in do you go into any detail on the larger features. It's very very easy to get sucked into noodling on facial features right away, but this is a mistake. The large shapes of the head, the angles of the neck, the sizes and shapes of the nose, chin and skull (with the hair) can be the real keys to getting the drawing to really look like that person.

Once you have the larger shapes set up to your satisfaction you can move into the features and such. Think in terms of shapes, compare the lengths and angles of one part of the face and head to another. You must let go of the pressure to "capture" the likeness of the person and instead notice the shapes of the parts of the nose, the angles and shapes of the chin, the ears, the eye sockets and brow, the relative sizes of the features to each other. All these things combine to give each person their unique set of proportions that make them look like themselves and nobody else. Only after you've laid in all the shapes do you go in and noodle any of the juicy stuff like the eyes and shading.

If you've got the basic shapes down, you've probably "caught" the essence of the person's likeness and you'll still have a decent drawing even if your subject gets up and leaves you in the lurch. If you practice and pick up some decent anatomy and drawing books it can help immensely with understanding the shapes you're trying to capture. Noses, ears and eyes have specific anatomic structure; if you know what those basic structures are it saves you precious time; you know what you're drawing already and then you can focus more on what makes this person's anatomy subtly different. It makes the drawing process much easier and you can relax really enjoy it.

But let's be honest, most of us don't want to sit and work at it that hard. If you're not going for the really realistic stuff, just relax and let yourself draw the person in whatever way is comfortable for you. Everyone has their own way of seeing things. It's not always easy to get it onto paper, but relaxing into it, allowing it to be what it is, can be one of the most effective ways to create a drawing that you'll look at later and smile at.

Kirk during a long-ago D & D game.
People tend to sit for fairly long periods while gaming,
which makes them easy targets for sketching.
Kirk doesn't think he's this beefy, but I've always had a fondness for this drawing because it just catches the big loud Kirkish essence of how _I_ see him.
Pencil in sketchbook
Chuck drawn from a photo I took, as there's no way anyone would ever get him to hold still long enough to draw from life.
Pen and ink in sketchbook
Paul in a drawing with color added later.
Very loose pen and ink with colored pencil in sketchbook.
Jim Sanford during a lecture long ago
at an Academy of Art Illustration class.
Great instructor who has since passed away.
He is still missed.
Pencil in sketchbook.
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