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I don't think many people try.

Having a family to support certainly makes things more difficult, but if you're unnattached I believe you can just go after what you want. You'll survive.

Well. You go do what you want. But you should ensure that you don't come back with your hands empty.

For example, you take one year off to study and experiment with JavaScript. You waste one year and burn all your expenses and makes no money but you made something amazing (let's say a popular JavaScript library).

Since you come back after that one year and your hand are not empty, you should probably find a good job at a nice company or startup.

It's something you tell developers so they can go to sleep at night, but a lot of us don't actually have the economic freedom to do that.

http://en.wikipedia.org/wiki/Black_swan_theory