Portrait Drawing Tips

pencil drawings Portrait Drawing Tips

Portrait Drawing Tips

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This new challenge starts today, December 1, 2016, and, by December 31, I hope to be a master of portrait drawing.

Especially before I smoothed out my face, it looked as if I had just been cleaning chimneys.

What other techniques do you use to draw faces? Have you tried any of these and noticed improvement? Let me know your portrait drawing experiences in the comments below. 26 Comments Leave a Reply

For my first piece, rather than drawing the model from the course, I’ve chosen to draw Derren Brown, who originally inspired me to pursuit portrait drawing.

Clearly, I have some amount of obsessive compulsiveness going on, but I’m curious to know what you think…

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.

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This was a bit of a mistake, but a good learning opportunity. As a result of this decision, unlike with my Derren portrait, I had to pencil-shade the mid-tones on my face, leading to a slightly dirtier portrait. (In the case with Derren, where there were midtones, I left the blank paper untouched and clean).

My CritiqueThe face shape is accurateThe level of the features is accurateThe angle of the features is accurateThe center line curves a little too quickly as it moves up between the eyesThe neck shape is inaccurate — I especially misestimated the starting point of the neck on the right side.

Above the right eye, the angle of the head/hair is too steepThe peak of the head is too steepThe angle of the hair above the ear isn’t steep enough

Lastly, I blocked in the main structures of the ear and added an outline for the beard.

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Today, I flew from San Francisco to Florida to meet up with my family for a few days. I’ll be here until January 4th.

For some (perhaps, legal) reason, most apartments in San Francisco don’t have overhead lights in their main living areas. Usually, apartments only have overhead lights in the bathroom and (sometimes) the kitchen, which is the case for my apartment.

Last month, I memorized a shuffled deck of cards in under two minutes, which required obsessive, consistent practice. If I were to stop practicing, over time I would lose this skill.

Picking up where I left off, I continued to block in shapes for the features.

This is mostly because I’m very bullish on this entire project.

However, I don’t think the same is true for my newly-found drawing skills. Mostly because… I didn’t learn anything new this month.

With the construction lines as references, I was then ready to start blocking in the facial features.

I’ve had strong artistic tendencies since I was a kid, but I’ve never invested much in my fine art skills. Instead, I’ve channeled my artistic impulses mainly through music, film, and computer-aided design.

Before I drew my self-portrait, I drew a portrait of Derren Brown.

So, thank you people of San Francisco for not getting totally creeped out. I promise I’ll stop soon.

I considered drawing in the bathroom, but this isn’t entirely comfortable. Especially because I was worried that the portrait would get wet/damaged on the sink, whose counter is the most viable drawing area.

The relative tones of the face to the hair are much more accurate now, which helps with realism.The shape of the hair on the left side of the portrait wasn’t quite right, so this gave me the chance to fix it.Here’s the before…And the after

I continued in this way, until I outlined the entire shape of the head.

Yesterday, I started following along with the Vitruvian Studio portrait course, and began drawing a portrait of Derren Brown.

It almost feels unnatural to add tonal values to the sketch, as if I’m defacing something I worked hard to create.

I started by adjusting the center line slightly for the nose, and marking the nose’s outer boundary.

I ended up across the street from my apartment at a well-lit coworking space, which was great for drawing, but not-so-great for picture-taking. The abundance of overhead lights meant that, however I positioned my body, I was always casting a shadow on the portrait.

Related PostsDrawing a Realistic Head: Bringing Faces to LifeAdorable Art: Learn How to Draw and Paint a DucklingReady to Advance Your Art? Draw These 8 Challenging Subjects

These steps are based on the excellent portrait drawing course by Vitruvian Studio, which I highly recommend you purchase if you are serious about learning how to draw.

Something to think about as you start planning your 2017 resolutions…

I start by blocking in shadow areas near the mouth, on the forehead, and on the neck.

Interestingly, this completeness is a bit problematic: Because the sketch feels whole (and, from my perspective, represents an interesting, standalone piece of art), I struggle to continue working on it.

Overall, I’m pretty happy with the outcome — especially since I sketched this fairly quickly. I guess that means I’m improving…

Considering where I started only nine days ago (see the before portrait), it’s hard for me to believe that I actually drew this. It’s not perfect, but I’m definitely excited about the outcome.

Take a look at the self-portrait side-by-side with the Derren Brown portrait. My head is noticeably smaller.

24 days ago, to kick off December’s challenge, I tried to draw a self-portrait.

Checking in Photoshop, everything seems pretty accurate. Although, the low point of the chin may be slightly too far left.

Part of me lacks the motivation to continue drawing, as I feel like I’ve already accomplished my goal. The other (more overpowering) part of me realizes that I have another 21 days to improve even further, so that’s what I plan to do.

Tomorrow, I’ll make some minor tweaks, sign it, and hang it on the wall.

Finally, I completed the neck, decided not to address the clothes, signed it, and I was done.

Yesterday, I declared that today I would start working on the mouth and cheek areas of my self-portrait. And yet, somehow, the day is over, and the mouth and cheek areas are still naked.

Nine days ago, I began my 30-day quest to learn how to draw photorealistic portraits. Since then, I’ve watched the entire 10 hours of the Vitruvian Studio drawing course, as well as spent 14.5 hours working on my first portrait.

Basically, I’ve used everything at my disposal (except for fine arts skills) to create artistically.

In January, 2016, I was just starting to develop the itch to draw/paint portraits. In an attempt to make something that was commercially viable (to cover the cost of materials), I decided to paint a portrait of Donald Trump.

However, Derren didn’t inspire me with his drawings, but rather, his paintings, like these…

Portrait of French actress Léa Seydoux by Antonella Avogadro

Perhaps, I’m just stalling out of fear: Once the mouth and cheek are developed, I’ll have a much better idea if the portrait is any good.

As a result, the portrait definitely has a stunning roundness, but I wouldn’t call it photorealistic.

While technology-aided art still should probably count as art (in some capacity), this month, I’m committed to creating using only the tools shown below: 9 black pencils, 1 white pencil, a few different erasers, and a gray piece of paper (which I’ll explain another time).

Should I just start the next challenge once I finish the previous one? I’m not sure. On one hand, this seems reasonable and time-efficient. On the other hand, there is something very tidy about starting on the first of each month.

It’s starting to look like me, but it still looks like a drawing — mostly because I haven’t blended the newly developed areas like the neck, cheek, mouth, ear, forehead, etc. Pretty much the whole thing.

Tomorrow, I’ll continue following the course, and start drawing in the facial features.

Firstly, the most useful technique to get started and past the initial fear is to simplify the major shapes of the face.

Observation about today’s session: Based on the output from today, it may seem like today’s drawing was the most technically challenging. But, in fact, I found just the opposite.

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

During high school, whenever I was tasked with making someone a gift, I usually opted to construct a custom Warhol-inspired portrait out of Legos.

While the Derren Brown portrait (with its ultra-contrasty tonal range) may be a more dynamic portrait, my self portrait seems closer to photorealism, which is the main improvement I was aiming for.

I’ve been holding off on the blending because my blending stump is unusably dirty.

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.

In particular, I’m going try to reduce the amount of time necessary to complete a portrait like this. With some practice, I think I can reduce my time down from 14.5 hours to 4–5 hours.

Anyway, continuing with this theme, today, I want to share an interesting struggle.

Last month, when I was learning to memorize a deck of cards at grandmaster speeds, I started unintentionally seeing playing cards in the real-world. In particular, real-world things (like wheelchairs and airplanes), which have association in my mnemonic system, were triggering images of playing cards, without any conscious thought on my part.

Anyway, I think the takeaway is that I need to invest in a better pencil sharpener…

While I am still very positive about this project, and happily take on the micro-challenges, I thought sharing some of these things would be more interesting than writing about how every day is always better than the last.

Today, I spent 30 minutes sketching the head shape and feature guides.

You can decide if this is cheating or not, but either way, this month is going to be different. This month, I am actually going to invest in my fine art skills. This month, I’m going to take a pencil and paper, and nothing else, and make it happen.

Finally, I detail the ear, which is one of my favorite parts of the whole process. (Ears are just weird looking and fun to draw)

Since the demo portrait in course is based on a long-haired female model, I had to do a bit more freestyling at this point. I think it works.

My 2016 highlights2016 was my first full year living in San Francisco and also my first full year as a post-college “working adult”.medium.com

It’s still hard to tell whether I’ll be successful, but we’ll find out soon…

Nevertheless, I must continue. So, here I go… Time to temporarily deface my work.

In fact, challenges are probably a good thing (I hope). Ideally, they push me to become a better artist.

Here are two portraits that I made for my cousins Adam and Marissa.

The first module of the course focuses on mapping out the portrait, which includes determining the shape of the head and locating the features.

In my life, I’ve created a fair bit of (what I’ll call) art. However, I’ve done so, not by relying on well-developed fine art skills, but instead, by cheating my way through the artistic process.

If you are drawing from an image, then you can even draw the shapes on your reference photo before you draw them on your paper. This will help you get a good understanding of proportions and the distances between features.

And while this seems like a major leap from my drawing studies, I now have the artistic confidence to attempt a painting like this, without any (or very little) additional instruction.

With the features and shadows blocked in, I detailed the features, starting with the eyes.

I think this is going to be a theme for the entire Month to Master project: If my practice is deliberate and consistent, it’s going to take a lot less time than expected to master these seemingly expert-level skills.

Measuring success for this challenge is certainly more subjective than last month (where I successfully memorized a deck of cards in less than 2 minutes).

With the neck and shoulders in place, it again didn’t look right. So, I checked more angles and made adjustments as necessary (mostly to broaden the jaw)

It turns out drawing is very similar. From the outside, it seems much more complex than it actually is. However, once you learn the two or three basic principles, drawing (at least, at my level) becomes nearly as straight forward as doing your laundry.

So far, so good. Tomorrow, I’ll start blocking in the features.

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.

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

In particular, as I said on Day 35, I believe that it’s most important to accurately capture the proportions of the head, the head shape, and the level of the features. If these things are done correctly, the rest of the process is very forgiving. If not, the portrait will end up beautifully shaded, but won’t look like the subject.

Finally, I added in shapes for the eyelids and eyes, and finished up for the day.

All of these tips are aimed at improving and refining our observational skills and analyzing the individual and unique proportions of the person we are sketching. Give them a try and see how, after just a couple of attempts, you will start to notice improvement with ever new sketch you create.

I continued with the upper part of the beard, and finished up for the day.

Today, I spent 2.5 hours starting the course and beginning my first portrait.

Next, I included the eye sockets and some more detail around the nose.

Then, I simply filled in the sketch with paint according to my computer-generated instructions.

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

Instead, I got caught up making micro-changes to the parts of the portrait I’ve already worked on (the eyes, nose, forehead, etc.). It seems I can make small improvements forever.

With Derren, I wanted to ensure the portrait emanated three-dimensionality, so I pushed aggressively on the contrast of the portrait. I also didn’t care much for the micro-gradations of shadow/light, as I was more concerned with the correctness of the bigger shapes.

I continue with my black pencil, darkening the other eyebrow and the hair.

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 is tremendously encouraging, to witness as we slowly improve our skills and get better right before our very eyes. After all, that’s what practice is all about, nothing but a beautiful journey of discovering how much we are capable of.

Purposefully, I chose to base my self-portrait on a photo with a tighter tonal range, since I wanted to challenge and push my abilities (Drawing a portrait with heavy contrast requires less subtly and is, in my opinion, easier).

In 20 years, even if I don’t practice from now until then, as long as I can remember triangulation and outside-in shading, I will be able to fully replicate my results from this month.

So far, the portrait doesn’t look like much, but I still learned a bunch today. I particularly like the triangulation technique, which makes drawing much more procedural and mathematical (a.k.a. easier for me).

I did, however, bring a Rubik’s Cube with me in preparation for January’s challenge (which starts in two days).

After checking the angles again, I updated these two new points.

Today, after another 2.5 hours of work, I finally completed my Derren Brown portrait.

I left all my drawing supplies behind, so I’m definitely not drawing any more this month.

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

Derren is a British illusionist, who I’ve been following for a while now, and who, I recently learned, casually paints portraits on the side.

In this case, the best I can do is show a photo that demonstrates the level of drawing I’m aiming to reach…

1. LikenessOverall, the likeness is strong. The portrait unequivocally looks like me. Although, it isn’t perfect.My expression/emotion in the portrait is plausibly mine, particularly in the eyes.The shape of hair near the ear and back of the head is very accurate.

However, the hair line doesn’t seem completely right, and it’s probably the second biggest reason why the portrait doesn’t look perfectly like me. The hair line should probably come down on the forehead and should be less rounded.

When I snapped a photo of myself (on which I based this portrait), I had just gotten a shorter-than-normal haircut, which is probably why I’m not used to the haircut I drew.On paper, I feel I captured the nose perfectly, but, as a result of the shadow, it may seem slightly too small/short.

To address this, I could have accentuated the tonal difference between the cheek and the shadowed part of the nose, but I wanted to remain as tonally accurate as possible and chose not to.I’m very happy with how the neck turned out.

Its weight and main features (the Adam’s apple and the notch at my collar line) seem accurate.There is something odd about the ear. It seems a bit out of place.The eyebrows may be the slightest bit thin, but they are very close to reality.

The biggest potential miss is my cheek. While I do have prominent cheeks when I smile (which I’m not doing here), I also have a fairly slender face and a reasonably defined jaw. Depending on how I look at the cheek, it sometimes appears too round and too full.

Other times, when I look at the portrait, my eye renders this area properly. If anything, I probably could have made the bottom of the face (in the rolling shadow) a bit more angular.

Again, I think this is okay compositionally, but it’s still a bit of a problem — particularly, for two reasons.

In most of my posts, I tend to be pretty positive (i.e. “Whoa, today went better than expected…”, “I’m really pleased with today’s progress…”, “I can’t believe how good this is…”, etc.).

Tim Jenison, on the other hand, does have something worth sharing. Without any artistic training, he painted a nearly-exact replica of a Vermeer painting solely using optical techniques.

Nevertheless, I will persist, since, even with the sizing mistake (and the associated challenges), I’m quite happy with the portrait so far.

Tomorrow, I’ll starting adding tonal values (i.e. shading) to the drawing.

As I mentioned at the beginning of this month, British illusionist Derren Brown originally inspired me to start drawing portraits. In fact, to acknowledge this inspiration, Derren was the subject of my first portrait.

Even with the narrow tonal range, my self-portrait still maintains a believable roundness and depth.

I started by arbitrarily drawing two lines on the page to indicate the level of the top of the head and the level of the bottom of the head.

Today, I’m going to practice finding the correct proportions of the subject’s head using a few celebrities: Matt Damon, Natalie Portman, and Morgan Freeman.

For the month of December, my goal is to draw a realistic self-portrait with only pencil and paper. Along the way, in order to learn the fundamentals of drawing and portraiture, I will also draw many other faces, which will hopefully keep this month’s posts more varied and interesting.

If you take the image all at once and dwell on how many details you have to draw and how difficult it will be, trying to tackle drawing a portrait would be intimidating for anyone! You can make the process significantly less daunting by taking it one step at a time.

Then, I marked eye level, to start gauging the features’ vertical placement.

The head was now looking pretty good, but the neck and shoulders needed a few adjustments. I retriangulated, and adjusted the collar upwards.

Tim’s journey is documented in the Penn and Teller-produced film “Tim’s Vermeer”, which I highly recommend you check out.

Although today’s darkening session improved things, the portrait still seems a bit odd and unbalanced because of the nakedness of the mouth and cheek. I’ll start tackling those areas tomorrow.

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

I think that’s a pretty cool thing, so look out for my Medium post in 20 years.

I made a bit of a mistake here. I drew the horizontal construction lines perpendicular to the center line (which seemed reasonable), but did not mimic the angle of the features in the actual drawing.

The portrait just feels balanced at this point. As soon as I start adding tonal values, that balance will be disrupted, and won’t return until I’m nearly done with the whole portrait.

Thus, to set a baseline for this month’s challenge, I’ve drawn a before self-portrait with my current drawing skills. Although it’s not the absolute worst thing ever drawn, it sadly doesn’t look very much like me.

Nevertheless, even with these critiques in isolation, the portrait as a whole comes together nicely and captures a strong likeness. Thus, I’ve left it as is, since I care more about an overall likeness (versus a non-cohesive collection of individually accurate features).

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).

Gary Faigin, Craftsy instructor, said that drawing portraits is one of the most magical things there is because, by using the simplest of tools on a blank piece of paper, a person suddenly appears on it. I could not agree more, and I think he put into words exactly what the amazing beauty of the portraiture experience is all about.

Then, I arbitrarily marked, on the top level, the highest point of the head, and then used the angle between this point and the bottom of the chin, to locate the bottom of the chin on the page.

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

Today, I didn’t have too much time to draw. So, I quickly progressed the Matt Damon sketch I started two days ago.

M2M Day 33: There’s a science to drawing portraits, and it’s all based on trianglesToday, I spent 2.5 hours starting the drawing course and beginning my first portrait.medium.com

This is clearly not the right approach. Especially because… As I begin shading the mouth, I will need to make adjustments to the nose area, so everything fits together. As I begin shading the cheek, I will need to make adjustments to the eye area, so everything fits together. And so on.

Next, I start on the prominent eye. This is where the real defacing starts, as it’s going to be a while until it doesn’t look like I’m wearing makeup.

2. Analyze the way the features align:When drawing, it is easy to let your brain take charge and begin to draw what we think is there instead of going with a fully observation approach and drawing what we actually see.

One way to overcome this problem is to draw lines in order to analyze how the features align on the face. Using this technique will help you learn how things like the eyes, hairline, nose, ears, cheekbones, etc.

interact with each other.

Today, I spent an hour developing out the rest of my self-portrait.

With all the steps documented, it’s now time to deliberately practice the most important skills.

I’m happy with the result, and actually think the self-portrait looks a lot like me.

In the coming months, I plan to start sketching a portrait on canvas, and then experimenting with paint.

Watching Derren paint, it seems like there are clear parallels between shading a drawing and painting a portrait: He sets a mid-tone color, adds the lights and darks, works his way towards the middle, and then adds detail.

Because I spent the past two days meticulously locating and blocking in the features, it was very easy to add the incremental detail. (Trying to draw big shapes is much harder than trying to draw little shapes. Little shapes are a lot easier to visually understand and replicate)

I’m definitely eager to start a new challenge, since I like the idea of always being in pursuit of something (which maybe suggests that I need to learn how to relax). Nevertheless, instead, these past two months, I’ve finished both challenges on Day 24 (of the month), and thus, needed to wait, without a challenge, for a week, until the next one began/begins.

Following these straightforward tips to make drawing faces less intimidating and more enjoyable!

A smaller drawing offers smaller margins for error. If I slightly misplace the corner of the mouth or the height of the brow, the distance between the correct and incorrect placements represents a proportionally larger difference on a smaller drawing.

In other words, smaller drawings are less forgiving and errors are more pronounced.A smaller drawing means finer details. My pencil sharpener doesn’t seem to work very well with the pencils I have, which means I’m drawing the tiny eyelids on my self-portrait with a tree trunk.

Basically, the smaller drawing requires that I work in finer areas, which is challenging with the tools I have.

From a quick cheer to a standing ovation, clap to show how much you enjoyed this story.

However, in my past three posts (I made a mistake, Intentionally defacing my self-portrait, and Fighting for photorealism), I’ve tried to interrupt this trend, and share some of the day-to-day challenges I face.

As a result, the rest of my apartment is lit via Ikea floor lamps, which, although they do a 90% good job, it turns out, at night, there’s just not enough light for detail-oriented drawing.

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”).

Thus, this time around, with my self-portrait, I’m aiming to more closely match tones, while also paying attention to the smaller areas of light fall-off. With this attention, my hope is to create a more realistic rendering of my face.

Art Blog Learn to Sketch Better Portraits With Just 3 Simple Tips

I may need to invest in some powder graphite (but I’ll return to this later).

Tomorrow, I’ll go swing by the art store and pick up a few fresh ones.

After many more minutes of work on the eye, I stop for the night. I’ll continue more tomorrow.

Should I wait for the first of each month to start a new challenge, and enjoy my few days of relaxing (if available), or should I just use my extra time towards future challenges and start immediately?

For my first portrait of the month, I’m quite happy with how it turned out.

Since, without deconstruction, the kitchen table doesn’t fit through the bathroom door (I tried…), I needed to find somewhere else to work tonight.

Draw vertical and diagonal lines to get a sense of how the placement of the nose relates to the placement of the mouth, and chin; how the corner of the eye interacts with the neck and jawline; or the relationship between the eye and the edge of the nose.

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

After 7.5 hours of work (2.5 hours over the past three days), I’m finally hopefully that this portrait will resemble Derren Brown.

Since I was accurate with the face shape and the level of features, if I continued working, I suspect I would develop the face fairly accurately. As a result, I would likely have enough accurate information to gradually correct the major mistakes with the head and hair shape.

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?

Today, I continued working on my self-portrait. Although it’s coming together nicely, I made a mistake upfront that’s definitely costing me now.

Today, for the third day in a row, I spent 2.5 hours on my Derren Brown drawing. However, unlike the other days, today, I feel like I made a lot of progress.

Thus, once I finished drawing, I came back to my dark apartment to snap a photo.

This post is part of Max’s year-long accelerated learning project, Month to Master.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.

With these four outer points drawn, the next step is to draw in the shape of the head. To do this, I continued to triangulate more points, and draw in the necessary curves to connect them.

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

With each of the sketches, unlike with my Derren Brown portrait, I felt that I was able to see the angle on the subject and accurately replicate it on the page with limited effort.

Well, that’s not exactly right. While I didn’t cultivate any new drawing-enabled motor skills or artistic skills, I did learned to structure my already-existing skills inside of a better drawing process.

Less purposefully, I chose a photo where the midtone of my face was darker than the paper.

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

To do this, I used a new technique I learned called triangulation. To triangulate a new point, I first sight (try to visualize) the angles to this new point from two existing points. Then, I draw lines from the existing points in the direction of the new point based on the sighted angles. Finally, I mark the new point where the lines intersect.

This tip is closely related to the previous one. We are still drawing lines over our reference image, but this time their purpose is to measure distances.

The first thing I did today was add construction lines to my drawing. These construction lines are designed to act as landmarks and help me eventually place the facial features.

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.

Before, I get to that, though, let me first share today’s progress.

M2M Day 36: Throwing some shadeThis post is part of Month to Master, a 12-month accelerated learning project. For December, my goal is to draw a…medium.com

Clearly, there are major differences in realism between my starting drawing and this example portrait. So, if I can match the level of this example (which will be, of course, a subjective, but hopefully honest judgement), I will consider this challenge a success.

Today, I spent another 2.5 hours watching the course and working on the portrait.

In fact, I suspect that today was least consequential to the outcome of the portrait. If I mess up the shape of the head and the location of the features, I have very little chance of capturing a likeness. If the features are not quite accurately detailed, but in the right place, I still might have something…

In fact, in order to draw a reasonable portrait, you only need to know the two following skills:

The trick, then, is to create a mechanism to force deliberate and consistent practice month after month. This is the hard part about learning these new skills, not the time required.

This month, to learn how to draw portraits, I’ll be following the Portrait Drawing video course from Vitruvian Studio.

And while my most recent self-portrait is a major improvement, and does look very much like me, I still do have some quick critical thoughts on it, which I’ve broken down into two parts: 1. Likeness and 2. Artistry.

After seeing these, I decided I too would like to be the kind of person that casually paints impressively good portraits on the side.

Sketching the features of a face at the correct distance from each other is very important to achieve likeness. Some people have eyes that are closer together, others are wider apart, some have longer noses and others shorter ones. All of these details make up the person as a whole and define their individual and characteristic look. When you get the size and distance of the features right, a face becomes instantly recognizable and can come alive on the page.

With the topmost and bottommost points identified, I then needed to identify the leftmost and rightmost points.

Finishing the sketchDefacing the sketch (a.k.a. adding tonal values)Finishing the sketch

I’ve also experimented using optical tools (like mirrors and lens) to mechanically create. Although, I haven’t invested enough time to produce anything worth sharing.

With my self-portrait, I strayed from both of these advantages. For one, on purpose. For the other, less so.

Tomorrow, I’m going to go through my previous posts (1, 2, 3, 4, 5, 6) and write up a “Portrait Drawing Cheat Sheet”. Then, I’m going to break down the cheat sheet into isolated, practicable skills and drills, work on those individual skills for 1–2 weeks, and then start working on my self-portrait to finish off the month.

Last month, it only took me 22 hours to become a grandmaster of memory.

Here’s my attempt to locate the peak of his head, the lowest point of his chin (which is located on the chin’s left side), the leftmost point of his cheek, and the rightmost point of his ear.

First, I drew in the vertical center line, which will help me laterally place the features.

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

I picked up some new blending stumps today, and went to work smoothing the value changes over my face and neck. Here’s the result…

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Of course, these paintings are built on a prerequisite foundation of drawing, but they also introduce a whole new skill set that I would love to cultivate.

Here is my “Portrait Drawing Cheat Sheet”, which features step-by-step instructions on how to draw a portrait.

After working for about an hour, I was able to finish sketching the outline of the head, hair, and neck.

Yesterday, I declared this month’s challenge a success, noting the differences between my before and after self-portraits.

Getting to this point took me 2.5 hours, which was split between watching the video course and drawing my Derren portrait.

I added in the center line of the lips and the shadow on the nose.

There are also clearly major differences, like evaluating and mixing colors, general painting hygiene (letting paint dry, etc.), and best practices I’m probably not yet aware of.

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.

Just looking at the sketch, the head shapes seems a little narrow for Matt Damon. But, overlaid on the photo, it seems to match up.

In Photoshop, I overlaid my sketch on the photo to check. I was pretty accurate.

To me, drawing is a bit like doing your laundry. Before you do it for the first time, you feel it’s much more complicated than it actually is, and thus, you feel incapable of trying. Then, you’re shown that doing your laundry is only a matter of putting your clothes in the machine, pouring in some soap, and clicking a button. Much easier than you thought.

To check, I then sighted the angle between the two new points, ensuring this angle matches what I see on Derren’s head.

And here’s my attempt to locate the peak of her hair, the lowest point of her chin (again on the chin’s left side), the rightmost point of her cheek, the leftmost point of her hair, and the notch of her neck.

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

Now (and I hope this eventually wears off), when I see a new face, my first instinct is to estimate the ratio between the height and width of the head. Other times, I just look to see what shapes the eye sockets are. Or how prominent the brow ridge is. Or if the nose and brows equally break the face in thirds.

Then, I addressed the right half of the face — further developing the shadow.

I start by blackening one of the eyebrows. This is easy, and hopefully will help me build momentum.

Today, to celebrate the New Year, I decided to compile my personal highlights from 2016, which includes Month to Master, but also everything else from my life.

With these tonal contours in place, I darkened the shadow areas slightly, giving the portrait some roundness and three-dimensionality.

This portrait is the example drawn in the Vitruvian Studio Portrait Drawing Course, which is the course I’ll be following this month.

During the sketching phase of my self-portrait, I didn’t need to see precise tone, so sketching at night was no problem.

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).

If you are interested in sketching portraits you can learn a lot more about capturing the essence of a person with the Craftsy classes Drawing Facial Features and Traditional Portrait Drawing Techniques.

While these pieces may look like they required some amount of artistic genius to pull off (do they?), that’s really not the case. Instead, these pieces just required some clever computational analysis, planning in Photoshop, and executional patience (while glueing and placing each Lego piece).

For now, before I get to the painting, I’ll start off by mastering the drawing part of program.

The InstructionsMark the top of the head. Arbitrarily draw a line towards the top of the page. This represents the top of the head.Mark the bottom of the chin. Arbitrarily draw a line near the lower third of the page.

This represents the bottom of the chin.Mark the notch of the neck. On the subject, using your pencil as a guide, measure the distance from the lowest point of the head to the notch of the neck. Determine how many of these distances can fit inside the vertical distance of the head.

Use this is as guide to draw a horizontal line towards the bottom of the page to represent the notch of the neck.Find the highest point of the head. Arbitrarily determine a point on the top line. This represents the highest point of the head.

Often, on the subject, this point sits far back on the head.Find the lowest point of the chin. Using your pencil as a guide, determine the angle from the highest point of the head to the lowest point of the chin.

Draw a line at this angle from the highest point of the head (as marked on the page) down towards the bottom of the chin line. Draw a dash where these lines intersect. This intersection represents the lowest point of the chin.

Find the leftmost boundary. Identify the leftmost boundary on your subject. Determine the angle to this leftmost point from the highest point, and draw a line at that angle from the highest point towards the leftmost boundary on the page.

Do the same from the lowest point. Draw a marking where these two lines intersect. This intersection represents the leftmost boundary. The technique used to find this boundary is called triangulation.

Find the rightmost boundary. Again, triangulate from the highest and lowest points to find the rightmost boundary of the head.Check the angle. On the subject, use your pencil to find the angle between the leftmost and rightmost boundaries.

Check if this angle matches the angle represented on the page. If not, retriangulate and check again.Draw the outer-boundary of the head and hair. Triangulate points around the head and connect them with straight lines.

Once the general shape seems right, smooth out the kinks. Check the angles between various points on the subject and on the page to make sure everything looks right. If there seems to be inconsistencies, retriangulate and adjust.

Do the same for the hair line.Draw the vertical center line. Pick some central point that looks like its on the vertical center line. Triangulate from outer-points inwards to find this central point. Check the angle from the bottom/center of the chin to this point.

Use this as a guide to draw in the entire vertical center line. As the center line approaches the top of the head, it typically flattens, as it rounds back behind the head.Draw the level of the eyes. The level of the eyes typically falls about halfway between the top and bottom of the head.

Use this as a starting point. Draw in this level, and then check angles to confirm. Move up or down until everything checks out.Draw in the level of the brows and bottom of the nose. If you divide the face length into thirds, typically the level of the brows fall on the upper third line and the level of the nose falls on the bottom third line.

Use this as a starting point. Draw in these level, and the check angles to confirm. Move the level up or down until everything checks out.Draw in the level of the start of the nose. The nose begins somewhere between the level of the brows and the level of the eyes.

Gauge where this is and draw it in.Draw in the bottom and middle of the lips. If you divide the distance between the bottom of the nose and the bottom of the chin into halves, the level of the bottom of the lips typically falls at the halfway point.

Use this as a starting point to draw in this level. Then, gauge where the middle of the lips falls relative to the distance between the bottom of the lips and the bottom of the nose. Draw that in.Adjust the center line for the nose.

Starting from the level of the start of the nose, adjust the center line so its angle matches the center line of the nose. Typically this will be in two parts. The angle outwards from the level of the start of the nose to the peak of the nose, and the angle inwards from the peak of the nose to the bottom of the nose.

Adjust the center line for the mouth. The mouth typically has some volume, which pushes the center line forward. Adjust the center line forward below the nose to account for the volume in the mouth.Draw in the shape of the eyes and eye sockets.

Triangulate the corners of the eyes, and then draw in the complete shapes. Do the same for the lids and the eye sockets.Draw in the shape of the brows. Triangulate the corners of the brows, and then draw in the complete shapes.

Draw in the shape of the nose. Triangulate the peak of the nose and the wing of the nose. Then, draw in the complete shape.Draw in the shape of the mouth. Triangulate the corners of the mouth. Then, draw in the complete shape.

Draw in the level of the chin. Triangulate the level of the chin, and draw a line to distinguish the shape.Draw in the shape of the ear. Triangulate points of angle-change around the ear. Connect these points with appropriately angled lines, and then smooth out the kinks.

Draw in shadow shapes. Identify shapes of main shadow areas. Triangulate their boundaries and draw them in.Darken the shadow shapes. Lightly shade in the shadow areas of the portrait. Use a soft, clean paint brush to smooth out the material on the page.

This will introduce some 3-dimensionality to your portrait, which should help you better visualize if anything doesn’t seem quite right. If there is something that seems incorrect, fix it.Detail the eyes.

Draw in the iris, pupils, and other details.Detail the nose. Draw in the nostrils and other details.Detail the lips. Smooth out the shape of the lips.Detail the ear. Draw in some of the main inner land marks.

Key the drawing. Identify the lightest and darkest tones on the subject, and add these tones to the page.Modeling an area. Pick an area of the head (like the forehead), and detail some of the main places of tone-change.

Identify and add in the main light and dark areas. Using a shading stump and the necessary pencils, fill in the transition tones. To better see the shapes of highlights and shadow, squint your eyes until the face isn’t recognizable as a face, but rather a collection of tonal blobs.

Model the remaining areas. Continue as above until all areas are modeled.Sign it. And you’re done.

In the coming days, I will write a few detailed posts about what I’ve learned, how I plan to move forward, etc., but for now, I’ll just share the final photos of my progress.

However, now that I’m trying to carefully model the lights/shadows of my face, I need more light.

Rather than writing another M2M post today, I’ll encourage you to check out that post if you’re interested.

Progress still seems fairly slow on the drawing, but I’m making a conscious effort to work carefully through the blocking in phase (so I can practice what I’m learning, and so I can ensure the portrait is built on a strong foundation).

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

Once you’re equipped with these two techniques, you’ll be ready to follow the “Portrait Drawing Cheat Sheet” and draw your first portrait.

A few days ago, I finished drawing my first portrait. Since then, I’ve reread my notes, reviewed some parts of the course, and wrote up my “Portrait Drawing Cheat Sheet”.

However, before I make it happen, I thought it would be fun to share some of my previous works.

Today, like yesterday, I continued adding tonal values to the portrait. I spent a little less than two hours, and am getting really excited about the results.

This portrait has two big advantages over my self-portrait: 1. The tonal range over the face is much greater, and 2. The midtone of the face matches the tone of the paper.

I also drew in the level of the notch of the neck. The first time, I drew it too low, so I moved it up. I gauged this distances as a proposition of the head length.

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.

While the result is artistically interesting, much of the work was done by a projector. I created a paint-by-number blueprint (again in Photoshop), projected it onto the canvas, and traced it in pencil.

The most common shapes used to break up the face are circles and triangles, but you can use whichever shape comes closest to the elements in your reference. Look at your image — or live subject if you are drawing from life — and try to find the underlying shapes that create the structure of the face and skull.

Tomorrow, I’ll write up a more thorough critique. But until then, I’m declaring this month’s challenge a success.

Today, I only had ten minutes to draw, so I spent all ten darkening the hair and eyebrows on my self-portrait, until they were as black as I could get them.

This month, as I learn to draw faces, I’m experiencing a new phenomenon… For the past few days, I’ve found myself scrutinizing and deconstructing other people’s faces on the train, at work, on the street, at Whole Foods, etc. Wherever there is a face, I can’t help but try to analyze it, and imagine how I’d draw it.

Yesterday, I was able to sketch about 80% of the portrait. Today, I just need to add the final details.

During the month of December, I documented my entire learning process in a series of 31 daily blog posts, which are compiled here into a single narrative. In this article, you can relive my month of insights, frustrations, learning hacks, and triumphs, as I strive towards monthly mastery.

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).

To do so, tomorrow, I’ll focus, not on perfectly detailing the mouth and cheek, but instead, broadly blocking in the right tonal values.

So, I sighted the correct angles, and adjusted the construction lines accordingly.

At first, the blackness of the hair is a bit jarring, but it accurately represents the “exposure” I’m going for (where the hair is emitting no light, and thus, shows up as pure black).

I can’t seem to easily get the hair to be one smooth black mass. Instead, the grain of the paper is very noticeable, giving me a nice salted look. Even after aggressive blending with a blending stump and a dry brush, I still can’t get the material distributed nicely on the paper.

With the features in place, I next blocked in shapes for the shadows and highlights.

After my light-seeking adventure, here’s what I was able to accomplish.

With the general tones in place, I’ll have enough momentum to push the portrait towards completion.

For the past couple days, I’ve been itching to start my self-portrait. So, today, I did just that.

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.

Here I try to locate the peak of his head, the lowest point of his chin, the rightmost point of his ear, the leftmost point of his ear, and the notch of his neck.

Then, over the next 3.5 weeks, I completed a 10-hour drawing course, drew a few other people, and then spent 8 hours on a new self-portrait.

Although I’m loving the composition of my self-portrait, I’ve sadly draw everything 10–20% too small.

My tonal approach is noticeably different than that used on the Derren Brown portrait.

With the exception of the oddly tiny ear, everything else seems to line up well. The head shape, face shape, and hair shape seem accurate. The level of the features and the center line seem accurate. The wing of the nose is a bit too far to the right, but I really just threw that in for fun.

In other words, after practicing for about an hour per day for 26 days, I majorly improved my portrait drawing skills.

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).

Today, I spent a couple hours working on the eyes and nose area of my self-portrait.

In other words, if I can remember the process, which, in my opinion, only depends on two very straightforward insights, I will always be able to draw at the level I can now.

Today, I practiced triangulating the complete head shape and gauging the level of features.

Arguably, the contrast of the Derren Brown portrait makes it a more visually compelling portrait, but this is another topic completely (first, I wanted to master accurate portraiture before tackling well-composed portraiture).

Yesterday, I practiced triangulating the proportions of a few celebrity heads.

After spending nearly a month learning to draw portraits, I’m more convinced than ever that anyone can draw. Even if you don’t have any artistic talent.

Tomorrow, I need to finish the mouth, the ear, the neck, the lower part of the beard, and perhaps the clothing.

When compared with the before, the difference is pretty striking. In the before portrait, I look like a sickly, pencil-sketched version of myself, while the after version has a much nicer roundness and weight to it.

Portrait Drawing Tips