- Scott H Young - https://www.scotthyoung.com/blog -

30 Day Portrait Drawing Challenge

In July of 2016, I did a 30-day challenge to see how much improvement I could make in drawing faces.

I’ve done a rather extensive write-up which explains why I undertook the project, what techniques I used and implications for learning other subjects.

Here is a comparison of three self-portraits I undertook. The first was a self-portrait I did before starting the challenge. Being frustrated while trying to draw this was a big motivation for starting the challenge.

Next was a drawing I did on the first day of the challenge. Between the very first self-portrait and this one, I had spent roughly 20 hours working on general drawing skills through the course Drawing on the Right Side of the Brain [1].

Finally, this was my last drawing after thirty days and approximately 100 hours of practice:

Challenge Constraints


I decided to use a fixed-hours schedule for the project of five hours per day, Monday-Friday. This allowed me to work on the project while also concurrently maintaining my work responsibilities of writing articles and managing my business, although I worked less during this time.

I didn’t maintain a consistent schedule during the project (a mistake, I believe), sometimes doing work first, other times doing work after. Near the end of the project, I found it difficult to sustain five hours on the project because of the intense focus required, so I’m not sure I could have done a much more time-intensive project if I had undertaken the project full-time.


There are many methods for drawing portraits. Some which work quite well also manage to shortcut the essential perceptive processes. For instance, while tracing a photograph may produce impressive results, I doubt outsiders would consider it nearly as impressive, nor as clear a demonstration of artistic ability.

For this reason, I decided to exclude techniques such as drawing from a projection or grid. While I don’t dismiss anyone who uses these techniques, as I believe all techniques are equally valid, they simply didn’t encourage the improvement of the perceptual and artistic skills I wanted to improve during the challenge.

I did, on one occasion, use reference photo overlays on a working drawing to make adjustments, however, in general I stuck to techniques that only required a pencil and paper. (I did experiment with a ruler as well, however I found it unnecessary.)


In the beginning I used this Canson Mix Media Sketchbook [2] for both finished drawings and sketches. I also stuck with a simple HB pencil and white rubber eraser.

Following my Vitruvian course in the middle of the project, I got new materials including:

I did experiment with some other materials in the project—including some charcoal and ballpoint pens (which I also used for practicing sketching to limit my tendency to erase and redraw). However I did not use these on any of the finished drawings.

Challenge Process

In the beginning I started by doing one finished drawing per day, usually taking one to two hours, followed by line drawings to get better at placing the facial features correctly.

I would photograph a page, once finished, and overlay the reference photo for comparison in GIMP [5]. This allowed me to quickly see what mistakes I had made on each drawing, both to note trends and also to give me direct feedback to guide my perceptual processes of sensing what was wrong with particular drawings.

Originally I did line drawings, four to a page, spending around 15-20 minutes each. This was too slow, so I sped it up to 20 per page, 20 seconds each. I did about a 100 of these faster sketches before moving back to a middle-ground (4/page, 3-4 minutes each). For all of these I used reference overlays on each page and noted mistakes.

Midway through the challenge my technique for finished drawings had become established. Draw rough positions, look at it, guess what needed to be adjusted, erase and redraw. This could be quite frustrating with 10-15 redraws sometimes occurring, causing me to get sloppy.

I also noticed my improvement with line drawings started to slow midway through the challenge, without getting noticeably better or faster.

Looking around for better methods to break through my plateau, I stumbled upon a course by Vitruvian Studios on portrait drawing [6]. This taught a method of triangulation and blocking from the outside in.

I spent the remainder of the project focusing on mastering this technique, and spent less time on line drawings and my previous approach.

In the end, I believe my method formed a good synthesis of the advantages captured by each approach, and if I were to recommend someone following the process from scratch, I would suggest a mixture of quick line sketches along with following a more formal process like that taught by Vitruvian.

Challenge Drawings

Here you can see all of my drawings, in chronological order. This includes both finished drawings and sketches. I’ve also included some false starts (where I started a drawing and then abandoned it or redid it) and some attempts at different media (charcoal, pen) which didn’t go anywhere. I’ve put the document in Issuu, so it is easy to browse:

Here is a zip file containing all the GIMP files showing overlays of my work.

Download zip (800 MB) [7]

Here is the journal I maintained during the challenge, which can give you a sense of my thought processes as I went through the challenge (rather than my recollective efforts in this page and the description post).

Click here to see my daily journal (PDF) [8]

Repeating the Challenge for Yourself

What changes would I make if I wanted to suggest someone follow my process?

Here’s my suggestions:

  1. If you have limited drawing ability, or it’s been awhile since you drew things, I recommend starting with Drawing on the Right Side of the Brain. This course can be taken from a complete beginner level and focuses on generalized drawing skills. I followed this process myself and found it very useful (see the improvement between 1st and 2nd self-portraits).
  2. If you already have some ability to draw faces, I would start straight with the Vitruvian Portrait Drawing course. This course teaches a good foundation for drawing portraits, although the technique is somewhat elaborate and methodical and thus isn’t as amenable for quick sketches.
  3. Doing line drawings with reference overlays is very helpful, particularly if you want to get better at sketching faces. If I had to redo the challenge, I probably would have done this alongside the Vitruvian course from the beginning, but the ordering probably doesn’t represent a huge adjustment.

Ultimately, however, the design of this project was specifically tailored to my individual strengths and weaknesses. As such, I think it’s more important to note the principles used, but to be flexible in applying them depending on where your own strengths and weaknesses lie.

If you do not have 25 hours per week to invest, I believe the same results could have been achieved spread out over more time. So 5 hours per week over 5 months, might have created similar (or even better) progress than my challenge did. The inverse, of compressing the challenge to do more in less time could also have been effective, but I think it might have created a sacrifice in the quality of focus had I tried to do more hourse per day.