OH gosh yeah, work with strong lighting from single sources to start. I had the benefit of a really long art unit where we drew objects and cloth drapery with such setups. Really, what you need to know is the shape of the object you’re shading. Then you can figure out where shading goes.
A well-drawn object will often not have every detail drawn, but implied. There’s a lot of implying in art. This is why sketches with the groundwork visible often have way more lines than the finished and cleaned-up product - they help describe the intended object shape so the artist can choose which ones to draw in explicitly, and which to imply.
To that end, here is a pic I drew up with basically nothing but groundwork:
The top four are me constructing a generic male head shape. Note the sphere with it’s sides shaved to make the base for the skull. Also note the ‘cross’ on the front which determines where the face is looking, and roughly where the eyes will go and where the chin ends. I add in details in a very geometric fashion. This makes easy lines I can soften later, and allows me to think of what I am drawing as a 3D object much easier.
[size=7pt] (This is what happens when I read how Loomis does it, and oversimplify. I have ommitted guidelines for placing facial features with a good sense of proportion for the purpose of this tutorial. I have stopped using them personally, since I’ve drawn so many damn heads a lot of it is style/instinct now. This tutorial is just for thinking in 3D and lighting.)[/size]
So yes. The head is now an outline with unfinished, simple chunks with mostly-flat planes. With this, it becomes much easier to decide where shadows go. Pick a direction for your light source and go. You may find shadows overlap to almost completely obscure a good chunk of the face you’ve drawn interior details for. Don’t be afraid to leave these obscured if the lighting is extreme. The silhouette the shadow creates will heavily imply what should be there, and an observer will assume correctly. Again, lots of implying in art.
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The first bottom one might be comparable to outdoors in the sun: lots of reflected light so the surfaces are mostly unshaded, but parts that are much deeper (under eyebrows, inside the ear) get very dark very quickly.
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Second one, indoors with a bright window or lamp, maybe. To make it more extreme, I only used light, and very dark. Notice how the nose both is dark on one side, and casts a shadow that covers more of the cheek beside it. The man’s left ear and sideburns would not be drawn in if at all, but the silhouette tells us where they would be anyway.
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Third one may have errors of my own making, this is a weird angle that doesn’t come up a lot. It mostly highlights how parts of the object closer to the light source can completely obscure details above them. For instance, the upper cheekbones and eyes both become totally darkened, because the jaw and lower cheeks stick out so far that no light makes it to them. The upper eyes/underside of the brow however, jut out enough to again be very bright.
Actually, let’s go with “All of these pics are imperfect”. I used no references. However, I get away with things looking passably okay, because enough has been implied to get the ideas across.
Implication is your hero.