"I don't know how to draw" -many of my friends, simultaneously dismissing drawing as out of reach and as a challenging hobby in which they fear they could not be good at - at least in the crucial initial stages (the fear of peer judgement)

If you want to learn how to draw, you can learn how to draw. You start out drawing lines and blocks, move on to cylinders, than to pots and pans, shoes, chairs, simple still-lifes and make the leap to live models. If you really want to become a legitimate skilled artist, you can become one. It just may take 9 years... [1] Like anything, you will need to work on it as often as possible - to the point where you just enjoy doing it (the classic doodling for fun). Doing art for money isn't realistic for most people [2]. There were always be people who are natural artists, people who make skilled drawing look effortless - remember as a coder - what you do is not easy - and it makes money - and it can exercise our problem solving creativity - all the while being a marketable skill.

I've been taking a progression of art classes for over a year and a half now. This is actually a long time in art class world. Really enjoying the escape from coding. It rocks because you lose yourself (like when you are on a focused coding tear). Have gotten much better yet have still so far to go. Have plateaued many times.

Drawing is all about the relation of shapes to each other. Drawing is about drawing what something actually looks like not what you think it looks like (drawing what you think something looks like and having it turn out to be what it actually looks like is the artistic equivalent of 'perfect pitch')

I've always wanted to be able to draw portraits. Portrait drawing is about the relation of shapes - but has the additional constraint of very little tolerance for off-by-one errors. Everyone is particularly attuned to facial recognition - lines that are off by even a millimeter or a fraction of an inch (by position or more generally - the angle) - you notice that. It is the difference between a portrait that looks like someone, a portrait that looks like someone else (but not her).

The thing that has troubled/stopped me most was trying to draw what I thought the eye/nose looked like and actually drawing what it looks like. My internal model of what the eye/nose looks like is flawed because I lack experience.

If you want to get better in portrait drawing and don't have the luxury of a live model posing for you, don't draw from pictures. Draw from live TV (like a newscast where the poses are relatively static but still fluid).

As an aside, if you look at other people's portraits of the model - there is usually part of the portrait that resembles them.

One of my teachers was amazing. She could take a blank piece of paper and in 15 min. create the person's portrait, capture their essence. If she worked on it more and more, it got even better. But she got the basic essence in a very short time.
She didn't make mistakes in positioning - like most of us in class did (we did get better by the end of the course) - to draw fast - you need to draw very accurately and with confidence. Mistakes can be corrected, up to a point.
If you don't draw the eye as it really looks, you can easily end up with something that looks like an egyptian mummy. There is a very clear orbital socket that needs to be shaded/drawn - without that the eye isn't an eye. Shading is so, so important.

Adding the little stuff to your drawing - like adding a little more shading to the half/side of the pupil that is on the dark side (away from the light) makes a difference. By itself, it doesn't add up, but it makes it look better - when adding all the other little stuff.

Now, drawing in public (e.g. someone's portrait for money in 15 min.) is a whole different ballgame. At least, starting with a controlled environment (precise teacher feedback) is a start. I believe the key is to have the basics down (and basically do a Mr. Potato Head from your experience drawing the basics)

[1] "Journey of an Absolute Rookie: Paintings and Sketches"
9 years...

http://www.conceptart.org/forums/showthread.php?t=870

[2] http://www.nytimes.com/roomfordebate/2011/11/22/how-the-futu...