Tim Ferris, the author of the book The Four Hour Workweek, has a very useful exercise which he calls Fearlining. You focus on a decision that you are considering (e.g. taking 6 months off to travel the world) and explore the worst that could happen if you do it (or don't do it). Another crucial part is to think about the actions you could take to minimize the consequent potential disasters you are concocting in your brain. Every time that I have applied Fearlining, I came to the conclusion that the risks are really not that big and insurmountable as I have believed. If you change your perspective by working through what could go wrong and seeing that the tectonic plates won't shift as a result, you will feel more comfortable to move out of your comfort zone. Check out the video below.
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