On Drawing Portraits

When I was a freshman in college, I decided to get a table at the annual craft fair to make some money. Except I didn’t have any scarfs knitted, candles poured, or cards painted, so I had to come up with something quick. I decided to do live portraits, in ink. 

It was terrifying because there was a real chance I’d make someone pay eight dollars for a terrible rendition of their face. And because Bard College is kind of an awkward place where eye contact with strangers is usually avoided. So I worried people wouldn’t seek out being stared at for ten whole minutes.

But I drew over 20 portraits that day. Every time someone sat down, I focused less on drawing them, and more on seeing them. I realized that the input I needed was not just the shape of their jaw and the texture of their hair, but the feeling I got from being near them. As long as I focused on that, my hand knew what to do.

I felt like I got to know some people without having to talk very much. They were willing to sit and as I let my eyes absorb their personality and their presence. And they seemed genuinely happy with the lines that wound up on the paper that way.

One of the people I met that day was a staffer at the college, who asked me if I would draw portraits at her mother’s birthday party. Two weeks later, she came to get me in her pick-up truck. Holding my bag of drawing paper and japanese pens, I looked out the window as we left the manicured lawns of my liberal arts bubble, got onto the highway and eventually stopped in what I now know is a trailer park.

It turns out I was the attraction of the party. Surrounded by plastic folding chairs, disposable plates and supermarket cake, I drew nearly every guest. I captured missing teeth and greasy pony tails as well as pudgy eight year olds and wrinkled upper lips, and it’s still one of the best memories I have from that time. I didn’t even talk to them much, didn’t catch most of their names, but by drawing them, I connected. 

I really got to see them and they seemed so happy to be seen.


Here’s a portrait of my mom, who doesn’t do any drawing but sees people like no other.

How illustrations work

While you’re on vacation taking a walk, you might find yourself staring at a tree. All relaxed and content, you suddenly notice the strength of the stem, the fragility of the leaves, roots being grounded while the branches reach for light—beautiful! 

But the next week, when you’re commuting to work again, it’s all gone. If you’re like me, you’re running to the subway in a dirty part of Brooklyn, and you barely register any trees at all. If you do, you simply notice there’s a plastic bag stuck between the branches.

What’s so great about illustrations is that they can bring you vacation-trees during a stressful workweek. Illustrators can look at a tree for you, work to see it fully, and then work again to draw the essence of what they saw. That drawing may not be majestic at all. It might be messy. It might be three lines on white paper. But if done right, a rich image will form in your mind every time you look at it.

This is how illustrations work. They need not be detailed or complex to be effective. They just need to provide the ingredients with which your mind can do its magic. 

So if you’re drawing a tree, you don’t need to copy the exact curves and texture of world’s most beautiful branch. You have to draw those shapes that will help your audience picture one, or even better: feel one.

It’s very difficult. But very magical when it works.

An example:

This is a drawing by Oamul Lu (oamul.com), whose illustrations work for me every time. Looking at the brush strokes gives my eyes the input I need for my brain to reconstruct the feeling I felt on my last summer hike in the catskills.

Let me know if it works for you, too, in the comments below.

By Oamul Lu (oamul.com)

Five methods for lively drawings

For a drawing to feel alive, it needs a bit of randomness, a bit of unintended movement.

This can be quite difficult. I struggle with it in most drawings I make, maybe because my elementary school teachers loved my super careful drawings so much. I was both creative and neat – what else could anyone want? A little more liveliness, I now think.

So, I’m working to let go a little bit. It’s counterintuitive, but to draw the right line, I have to stop myself from trying so hard to draw the right line; I need to trust my hand.

It still takes work, but I have found a few techniques that help a lot:

  1. Speed up – Go fast enough for your eyes to lose track a bit.
  2. Pretend you’re simply sketching to warm up – I have often drawn 18 versions of something, only to go back to the first one.
  3. Tell yourself to just have as much fun with it as you can for 10 minutes – its awesome if it works.
  4. Create version after version until you get so frustrated that you no longer care, and then keep going.
  5. Drink a glass of wine—not recommended, for obvious reasons.

These methods work because they help you worry less about the end-result. Numbers 1-3 are nice and you can try them anytime. If they’re not working, don’t worry—number four is on its way. 

For number four, the key is not to quit when you get frustrated. Many people fuss to create version after version until they start to feel very annoyed and then stop. But they are stopping right before it gets good.

An example:

Last year, I drew the labels for Spring Fireplace hot sauce bottles. We went through version and after, which became increasingly rough on my schedule. But just as I started feeling very frustrated, the right spontaneity made its way into my peach!

To me, the final version is both more solid and more free:


Who am I and why this blog

This blog is about drawing and illustration, but I am not a full-time illustrator; I actually run a program at an economics institute, which I very much enjoy. 

When I tell people I studied economics and now work at what you might call a think tank, I often get a serious look. It probably sounds like I know tax law, or that I can advise on what to invest in; serious-job-spreadsheet-stuff. I get a very different look when I say that I love to illustrate, too. 

It might be because it reminds everyone of drawing during childhood. And if you want to be an artist, in the serious adult sense, you’d paint, or sculpt. Or do design? Drawing and illustration can also sound like sketching, which is just a piece in the process for something more important, or doodling, which you do while you’re bored on the phone. 

But to me, it is just as serious as anything. Just as complex, and just as rewarding. I love seeing drawings, making drawings, and thinking about drawings as well as the process of drawing. I am always working on getting better, and I tend to be busy with a range of illustration projects alongside my job in economics.

This blog is about that work, why it is so valuable to me, and how it may be valuable to you, too. You won’t have to do any drawing to see what I mean. You just have to use your eyes a little differently. Just reading along might give you a new kind visual of sensitivity, and let you see things you more fully than before.