Let me see if I can put it into words...
It's all about ratios. Whenever I start a drawing or painting from life I put little lines as "landmarks" on the canvas. If I'm doing a head and shoulders portrait, I would first decide how tall I want the head on the canvas. That has nothing to do with measuring the model but is purely based on the composition I want in the painting. It can be much larger or much smaller than the dimensions the model actually takes up in my field of view. (Painting the model the actual size he or she takes up in my field of view would be "sight-size" drawing.)
Now the measuring starts. I first want to know how wide the face is compared to the height I've established. I measure the height of the live model's head by holding my pencil at arm's length. I visually line up the top of the pencil at the top of the model's head and move my thumb down the pencil 'til it's at the bottom of the chin. (Close one eye when you do this -- it's much easier!)
Then I hold my pencil horizontally and compare the width of the face with the height I've measured, with my thumb still in the same spot on the pencil. Let's say I find that the width of the actual model's head is two-thirds of its height. That ratio of two-thirds is the key.
On my canvas I then measure a width dimension that is two thirds of the length of the height marks that I've established. (You can use a ruler or any stick that is a useful length.) If the vertical head dimension I want on the canvas is 12 inches tall, I'd mark the outer edges of the head width at 8 inches, which is two-thirds of 12.
(Hence the math.)
This measuring process repeats over and over 'til you're confident that you have all the landmarks you need to get the likeness. You can measure from the outside in (head dimensions first) or from the inside out (using one of the features of the face to compare everything else to, for example).
The better you get at drawing the more this measuring process becomes automatic and you don't need the pencil held at arm's length any more to do your measuring. At some point in your development you'll be able to just mentally note that the model's mouth is one-and-a-half times the width of the nose, for example.
Hope that helps!
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