You have not found a way to connect your hobby to rationalism yet. It itches. You are not whole. It is forbidden to post an article entitled Rationalist Hobby on Less Wrong. You lie awake at three in the morning, trying to create puns.
-- Alicorn, Rationality Gothic 
(Note from 2017: This sequence was written before Alicorn's classic jab at people shoehorning rationality into random hobbies. I'm fairly embarrassed by it at this point, but don't have time to rewrite this into something I'm not embarrassed by, and several found it a very helpful introduction to drawing.)
((Also, this sequence ends abruptly when my 2011 life got in the way. If you get to the end and go "aarrg! what do I do next!?" the answer is "purchase 'Drawing on the Right Side of the Brain' and finding a figure drawing class))
This post begins a mini-sequence that discusses how to draw, reports on an experiment about teaching people how to draw, and examines how rationality and good drawing practices are related. (As it turns out, a fair amount)
I'm a professional artist. I have a fairly extensive background in traditional drawing, but most of my training is in computer animation. I chose my career because I liked the control offered by the computer - the ability to undo, to manipulate art in procedural ways, and most of all for the flexibility to duplicate things, repurpose them for different projects and combine my love of visual art with my love of game design, animation, and various other mixed media.
But now I work 10+ hours a day at an advertising agency. I spend all day getting paid to stare at a computer screen. Most of my other hobbies also involve staring at a computer screen. And many types of digital work are taxing on the same set of creative muscles, so at the end of the day I didn't have energy to work on the personal projects I wanted.
One option would be to get a different job that didn't tax those creative muscles or involve staring at a screen. I've actually considered getting a "physical" job - after years and thousands of dollars of college to get a nice posh job without physical labor, I actually think it might be better to get PAID to exercise. And instead, use my free time to channel my skills from colleges into personal creative projects that I'm passionate about.
I may do that some day, but I DO like my job, I like the people there, and I continue to learn important skills. So instead of modifying my job, I modified my hobbies. A few months ago I began drawing people - on subways, in coffee shops, in parks, etc. This gave me a new creative outlet, as well as a new social outlet. (Starting a conversation with "Hey, can I draw you?" is a pretty useful technique - not only does it provide an excuse to begin talking, but if you follow up with a good drawing, you've established right off the bat that you're an interesting person with a valuable skill. You've also flattered the other person a bit, and if the conversation enters a lull, it's okay - just draw for a while until you can think of something to say.)
So I've been getting better at traditional drawing, and better at social interaction, and more confident in general. And at a local Less Wrong meet up, it recently it became clear that...
- Other people wanted to learn to draw
- I wanted to learn to teach
- A few people wanted to model. So the "Drawing Less Wrong" meetup was born. I prepared some lesson plans and began holding 4-hour workshops.
What interested me was how much the study of drawing was relevant to rationality. Not only do you have to learn to observe reality (this is surprisingly hard), but you have to pretty much scrap your entire model of how you think drawing works. (Almost everything you will naturally gravitate towards is wrong). Most artists don't notice that they should be applying these lessons to the rest of their life, but I think the skills can generalize if attention is brought to that notion.
In the past, I've been to figure drawing workshops where I saw people go from not being able to draw much at all (one person showed up to class with a *horribly* copied manga drawing that they said had taken them 12 hours), to being able to execute a reasonable gesture drawing1 in about 60 seconds. It took them about 8 hours of dedicated practice. I wanted to try and replicate that.
Soon to follow are a collection of posts discussing the nature of talent, how to draw effectively, and lessons I learned from trying to teach people extremely counterintuitive models of reality.
 "Reasonable Gesture Drawing" is a specific phrase that means something to trained artists, which non-artists may misinterpret. It doesn't mean "looks amazing." It does mean that this person improved in important ways in a short time.
 I refuse to call it "Rationalism Gothic" because Rationalism means an oddly specific philosophical school that is actually kind of the opposite of what Less Wrong is about.