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Making of My Face icon:

(Software: NeoIcon/ Hardware: PowerMac 7500/100)

Like any form of illustration, before you begin, it's best to give a rough pencil sketch on paper. And also have in mind what kind of drawings you want, say a cartoon one or a serious one? I start by sketching roughly how my icon should look on a rough paper, and from there, it's easier to begin with mouse clicks in the computer.
(1) (2) (3)
I have a "square" face, so starting with a square would give a good guide for my features. Note I drew a bit up, allowing some space for chin. Remember you're dealing with pixels, when drawing curves, always do it slow and adjust accordingly, with more practice, you should realize the limitations. Don't worry about deleting or adding, you can always add it back, or delete them. Now I delete the top for clearer view of where my face will occupy the whole canvas.
(4) (5) (6)
I then just draw whatever I can to make it look like what I want it to be. Realize the left and right specs (eyes) is not balance, but visually it looks fine. Always do fine tuning when making icons, you will see the different results just by changing a few pixels, compare (4) with (5). Start with flat colors, get the colors right from 256 colors isn't that easy, but it's definitely enough.
(FINAL)
Finally, adding shadows and highlights will make it look more interesting. This is a very simple icon, with simple lines and flat. It took me around 20 minutes to create this icon, which then I created 30 different expressions of it.


How to sections:
 Making of Cuties icon (Strawberry):
 Making of My Face icon:




 
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