M2M Day 36: Throwing some shade

Max Deutsch
5 min readDec 7, 2016

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This post is part of Month to Master, a 12-month accelerated learning project. For December, my goal is to draw a realistic self-portrait with only pencil and paper.

Yesterday, after 7.5 hours of work, I finally finished sketching / laying out my first portrait. Today, I started adding tonal values (a.k.a. “shading the drawing”).

Before I show today’s progress, I want to share two techniques I learned that make it significantly easier to accurately add tonal values to portraits.

1. Start with the most extreme values and then meet in the middle

The human eye is really bad at assessing tonal values in isolation — which is why your brain thinks squares A and B below are very different colors, when, in fact, they are the same.

Thus, instead of relying on visual inferences, tonal values can be better approximated through a simple, not-so-interpretative procedure.

Here’s how it works:

Start by identifying the absolute darkest and absolute lightest areas of the drawing. For the darkest areas, shade them as dark as you can/want. For the lightest areas, highlight them as light as you can/want.

This establishes the entire tonal range of the drawing, which is called the key of the drawing.

Establishing the key is straightforward, and doesn’t require much visual interpretation (i.e. it’s easy to find the lightest lights and the darkest darks).

Once the key is established, and the lightest and darkest values are in place, the intermediate values need to be introduced. Again, this can be done procedurally, by identifying and shading/highlighting the areas which are slightly lighter than the darkest darks and slightly darker than the lightest lights. Continuing recursively in this way, the tonal values eventually meet in the middle, and the drawing (or the relevant part of the drawing) is complete.

2. Squint to better see tonal shapes

When keying the drawing (and developing tonal values in general) it’s important that the shapes of the tonal areas are captured accurately.

In other words, if the highlight on the forehead is angular, drawing it with rounded edges wouldn’t properly capture the form.

This sounds obvious, but again, your brain and visual system can play tricks on you. Your brain is attempting to see a face (via your psychologically skewed, emotions-based mental model of a face), and not just tonal blobs.

In fact, this psychological problem of misinterpreting faces is so common, there are entire drawing systems (like drawing upside down, drawing the negative space around the face, etc.) designed to combat these problems.

Side note: Here’s a video of Derren Brown, the subject of my portrait, when he used to have hair, experimenting with some of these alternative methods of painting. It’s a pretty cool trick.(If you’re going to watch, stick it out until the end).

In order to accurately see tonal shapes, and avoid psychological errors, I’ve found one method to be surprisingly successful: squinting.

Basically, you look at the area you want to draw, squint your eyes (so the image becomes blurred and your brain no longer sees a face), and identify the tonal shapes you see through your eyelashes. This works super well. (I didn’t invent this method, I’ve just validated that it works for me).

Today’s progress

With these techniques newly-learned, I began to add tonal values to my Derren Brown portrait.

First, I started with the eye.

In the course, the teacher mentioned that it’s good to start with a small area that exhibits the full range of tones.

However, the eye was too small to help effectively establish the key. So, I keyed the drawing more aggressively, starting with the shadow on the nose and the highlights on the forehead and cheek.

I continued shading the darkest areas along the right side of the face.

Additionally, while doing this, to check the accuracy of my key, I started developing the eye.

I finished up my key, by adding shadows to the lower face and the back of the head, and was ready to begin modeling the form (finding the intermediate values between the darks and lights).

I started with the forehead.

Added a bit more detail.

And then smoothed everything out.

This is where I stopped for the day, after another 2.5 hours of working.

Derren looks a bit too shiny right now — a bit like a mannequin or the Tin Man — but I’m optimistic that this effect will vanish once I model the rest of the form.

I’m guessing I have another 5 hours of work left on this.

Read the next post. Read the previous post.

Max Deutsch is an obsessive learner, product builder, guinea pig for Month to Master, and founder at Openmind.

If you want to follow along with Max’s year-long accelerated learning project, make sure to follow this Medium account.

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