How I learned to draw realistic portraits in only 30 days

On December 1, 2016, I asked myself the question: With only one month of practice, can I learn how to draw realistic portraits with only pencil and paper?

On December 24, 2016, after 26 hours of practice, I found out that the answer was yes.

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My self-portrait: Before and after

This article is the Table of Contents for the 31 daily blog posts I wrote during the month of December, which document my progress, insights, frustrations, learning techniques, and triumphs.

To relive my month, you can can either start on December 1, and then click the “Read the next post” link at the bottom of article (which I particularly recommend for this month’s series of posts).

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Or, you can pick and choose which articles sound interesting to you from this Table of Contents. I’ve written a short description for each post.

December 1 , 2016

This article introduces December’s challenge: To draw a realistic self-portrait with only pencil and paper. The article defines success and discusses my previous drawing experience.

This post also includes my before self-portrait to establish a baseline.

December 2, 2016

This article more deeply explores my past experiences with “art” in general. I like this article a lot, and think you’ll enjoy it.

December 3, 2016

With December’s challenge setup, it’s time to get to work. I begin the Vitruvian Studio Portrait Drawing Course, explain why I’m drawing Derren Brown for my first portrait, and start drawing.

Also, in this article, I describe what I believe is the most important drawing technique/insight. I’d encourage you to read this one.

December 4, 2016

I continue drawing Derren Brown, taking many photos along the way. In this article, I detail my progression up until the outline of the form is drawn.

December 5, 2016

In this article, I continue documenting my drawing progress, which seems to be fairly slow up until this point. Then, my drawing makes a quantum leap, and I share some commentary.

December 6, 2016

I finish my Derren Brown sketch, and am ready to start “shading” the drawing. In this article, I document my process, as well as share some insights on shading (i.e. adding tonal values).

December 7, 2016

I continue adding tonal values to the portrait, and start getting really excited about the results. It’s nearly done, and it’s looking better than I expected.

December 8, 2016

I finish the Derren Brown portrait, documenting the last few steps.

December 9, 2016

After finishing my Derren Brown portrait, I take a break from drawing for the day and instead celebrate the accomplishment. In this post, I share some additional commentary and a timelapse video I created of the drawing process.

December 10, 2016

After my weeklong sprint to learn how to draw portraits, I sit down, reread all my previous posts, and compile the “Portrait Drawing Cheat Sheet”. This post breaks down everything I learned about portrait drawing step-by-step.

For the rest of the month, this process doesn’t change — I just practice it a few more times.

December 11, 2016

The first step of drawing a portrait is to find the proportions of the head. If this isn’t done accurately, it doesn’t matter how well the rest of the portrait is executed — the portrait still won’t be quite right.

Thus, I practice finding the proportions of a few celebrity heads.

December 12, 2016

After accurately defining the proportions of the portrait, the next steps are to 1. Outline the shape of the head, neck, and shoulders, and 2. Gauging the level of the features (where the eyes, nose, and mouth sit on the page).

I practice these steps using a photo of Natalie Portman.

December 13, 2016

My practice with the Natalie Portman photo went well, but not perfect. So, I practice the same steps again using a portrait of Matt Damon.

December 14, 2016

After spending two weeks analyzing and drawing faces, I find that I start unintentionally analyzing faces “in the real world”. In this post, I discuss this socially awkward habit.

December 15, 2016

After two weeks of preparation, I feel ready to start drawing my self-portrait. I find the proportions of the portrait and sketch the outline of my head, which I document in a timelapse video.

December 16, 2016

I continue making progress on my self-portrait and I quickly realize that I made a mistake that ends up costing me a bit. In this post, other than documenting my progress, I share the mistake and discuss why it’s a problem.

December 17, 2016

I finish the underlying sketch for my self-portrait, which honestly looks awesome. As a result, I’m discouraged from shading the drawing: To do so, I need to temporarily “deface” the balance and completeness of the sketch. Nevertheless, I press on.

December 18, 2016

I continue shading my self-portrait, fighting for a more realistic tonal interpretation (compared with my Derren Brown portrait). In this post, I document the day’s progress.

December 19, 2016

In this post, I share a quirk about San Francisco housing laws, and how it’s affecting my portrait drawing abilities. Namely, I discuss how I deal with drawing in a dimly lit space.

I also continue drawing and share my progress.

December 20, 2016

I only have ten minutes to draw, so I spend all ten darkening the hair and eyebrows on my self-portrait, until they are as black as I can get them. This improves the portrait significantly.

December 21, 2016

I get stuck make minor edits to what I’ve already drawn, instead of making forward progress. This is clearly a form of procrastination, and I address it in this post.

December 22, 2016

I’m back on track. I spend the day finishing adding tonal values to the portrait. I still need to work on blending the tones, but the portrait is starting to look a lot like me.

December 23, 2016

I buy some fresh blending stumps at a nearby art store, and smooth out all the pencil markings on the drawing. The portrait significantly transforms and is essentially finished.

December 24, 2016

I make a few minor tweaks, sign the portrait, and I’m done.

In this post, I share the before and after portraits side-by-side, as well as a timelapse video of the entire drawing process for my self-portrait.

December 25, 2016

In this post, I write a long critique of my self-portrait. Particularly, I comment on the portrait’s 1. Likeness and 2. Artistry.

December 26, 2016

After spending nearly a month learning to draw portraits, I’m more convinced than ever that anyone can draw (even if they don’t have any artistic talent). In this post, I explain my thinking.

December 27, 2016

In this post, I share my ultimate goal to transition from drawing to painting. The post also includes some of my painting inspiration.

December 28, 2016

In a weird way, I don’t actually think I “learned” anything new this month. In this post, I explain what I mean.

December 29, 2016

With only three days left in the month, I am curious how much time I actually spent on December’s challenge. After aggregating the data from my practice logs and summing everything up, I find that I only spent 26 hours.

December 30, 2016

Now that I’ve finished December’s challenge, I’m itching to pursue something else. In this post, I discuss my struggle to wait for January’s challenge to begin.

December 31, 2016

For the last day of 2016, rather than focusing on drawing, I instead write a 4,500-word article summarizing my favorite personal highlights from 2016.

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