Tone is generally thought of as shadow. Beginners generally first sketch an outline of the shadow and then fill in the shadows bit-by-bit. They usually start with an eye and then grow out the shadows. Inevitably, the result is a chaos of non-cohesive darks and lights.
There are two distinct ways of viewing value: in Western culture we see value as shadow; in Eastern culture value is seen as color.
A Western spectator seeing a Chinese drawing will be struck by its flatness. Conversely, Chinese connoisseurs in the 18th century seeing for the first time European portraits were perplexed by the "dirty scuff-marks" under the nose.
Applying, or more correctly, constructing value should be done with a sculptural sensibility. That is, think of your sketch as a block of clay that is to be carved. Once roughly carved, you then model the surface forms with varying degrees of value while working their borders thus defining the shapes present in the skull.
A portrait sketching from life or (paper picture) starts with the drawing of the arabesque. Two things must be correctly sketched: 1. the form of the complete head; and 2. the proportions (i.e., length and angle relationships). This is a learned ability that no one is born with.
Once the arabesque has been struck, the complete head is then broken down into two pieces: a big light and a big dark. No more than that. At this stage, do not concern yourself with whether or not one area is darker than another. Only the major light/dark pattern counts.
Observe that squinting is a good way to more clearly see the tone patterns because you are not distracted by details.
A good rule of thumb is to carve an area in 2. For instance, if an observed dark area is not totally uniform in tone divide it in 2 and block-in the 2 slightly differing tones. Before long a complex yet unified array of tones will appear.
From the blocking-in of the large darks you can then effortlessly sketch the features. Over time you should try to remember the complete anatomy and "sense" the form 3-dimensionally. This, too, is a learned ability.
You must know your anatomy to be successful in sketching portraits even at the most fundamental level. Study the anatomy in small portions as you sketch along.
A good way to sketch is to toggle back and forth between line sketching and tonal sketching or hatching. Another way is to first do a complete line sketching of the subject. That is, to sketch a "map" of the head that includes all planes and marks the boundaries of the various tonal areas. As a second phase you can then hatch-in the right tones.
While you shade be constantly aware of the planes of the head and the direction of the light source.
Another expertise to be acquired is the expertise to cross-hatch patches in a flat and even manner. There is nothing more distracting than scratchy looking cross-hatching.
Finally, take note of a curious optical phenomenon called "simultaneous contrast". It happens when light and dark tones lie next to each other. In general, white is extroverted while black is introverted. The result is that the white area looks bigger than it is while the black area will look smaller.
In closing, keep the blocking-in procedure uncomplicated. Look for big masses first and then for the smaller ones. It is always better to draw from the general to the specific. And, at this stage, ignore the details.
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