The Art of You
If you want to learn to take better portraits, then you need to learn about your subjects and what they're going through when staring down the lens. Sure, you can pick some of this up through reading, but to really solidify this info and know it, turn the camera on yourself for bit.
For years I've had a standard response to the question "Can I take your photo." It's essentially, "Nope, I'm a photographer so I like to stay on the side of the lens that I like better!"
And while I do still try my best to stay out of other people's photographs, I've recently come to appreciate the self portrait. Despite my personal belief that I don't have a "good side."
The thing of it is, making self portraits is a great exercise in creativity that offers us, as photographers, lots of learning opportunities. For me personally, the self portrait is a perfect laboratory for learning more about lighting, posing, composition, exposure, and just about any aspect of my photography that I'm wanting to strengthen.
Now I know what you're thinking, something probably along the line of "I hate the way I look in photographs." Well, so do I. Get over it. And sure that may be easier said than done, but that's why I'm writing this, to give you all some simple tips to make it more palatable, and some reasons why it will be worth it.
15 minutes is all it takes
First off, you can make a pretty slick self portrait in about fifteen minutes, but that's not necessarily what I'm talking about. What I'm saying here is that you should plan on spending more than this, because it's not going to be until about the 15 minute mark that you'll start getting into the groove.
What do I mean by that?