Drawing 100 Portraits

4 min readOct 13, 2022

I’m drawing 100 portraits (at 16/100 as of writing this)! These are the unwritten (until right this moment) rules of my “draw 100 portraits” game:

Draw from any reference, prefer drawing from life. Using reference photos is acceptable, but actively seek opportunities to draw from life.
Fixed scope and variable time. Each portrait should reach my intuitive sense of “doneness.” This might sound vague but there’s a specific feeling when a picture is developed to a certain point and it holds together as a complete picture. The medium and the amount of time available factor into the sense of “doneness.” There are no deadlines, time goals, or time limits for individual drawings or for the 100 portraits overall.
Ink or charcoal.

The “do 100 of something” game has some magical side effects. The pressure is taken off of each drawing, it’s easier to see each one as an experiment, even while doing your best to make each one as well as you can. Each drawing can have its own question to explore or approach to try out, while also simply trying to make a nice portrait.

I’ve experimented with different picture sizes, types of charcoal and ink, general approaches to developing the picture, and a variety of portrait lighting and compositions. Over time this has made me more comfortable with a wider range of materials and approaches. At the beginning, I may have wondered how to get started or what steps to take and needed guidance to find a place to start. I may have fumbled with a new type of charcoal as my hands and eyes couldn’t predict how it would behave. But as I become more fluent in the overall cycle of starting and finishing a picture, the specific steps and materials matter less and less and I know there are a variety of starting points and paths to choose from. I’m sure there’s a generalized creativity lesson to take from that, and I’ll try to make note of that in my evergreen notes on creativity!

So why portraits? A lot of my paintings and drawings in the past have focused on still lifes and landscapes, but I’ve always enjoyed making portraits when I’ve had the opportunity. This is the classic trifecta of representational art — still life, landscape, and portraits / figures. I’m sure I’m not alone amongst draftspeople and painters in that I find I learn different but overlapping skills in each of these genres. Each has their own emphasis and nuance within the core drawing skills. Drawing portraits makes me a better landscape painter and vice versa. They use all the same muscles but stretch them differently.

However, people are also a uniquely fascinating and challenging to represent in a 2D illusion. The human form as a structure is highly complex and densely centered. The lines of the features seem perfectly designed to guide the eye within and around it, like the best graphic design. The edges of the nose lead us to see both the mouth and the eyes. The eyebrows keep our attention on the eyes and emphasize their expression. Even the small glint of reflection in the eye carries aliveness. And as fellow humans we are highly attuned to notice the smallest details in the image of another human. The smallest inaccuracy is easy to discern and makes the entire picture feel off. With a tree or a landscape you can get away with a bit of structural looseness, but with the human form it stands out immediately. I often wonder if a tree could see a picture of another tree if it would have the same problem. The attempt to perceive and record this richly entangled, densely alive structure is endlessly challenging.

The human image encourages our natural tendencies for storytelling and curiosity. We wonder about the person and about their expression. We might even imagine them filling the roles of mythic tales. What could they be looking at or thinking about? What are they like? What are they feeling and why? The portraits don’t come with social media profiles, but they give the same fascination of learning about someone through their profile picture.

Here are a few highlights from my portrait drawings so far. Here’s to the next 84!