It's important to chart new territory but here are three things to keep in mind to help minimize the amount of deserts we willingly walk into:
1. Am I already in a desert (or a few deserts)?
2. Is there a way I can pair this new 'something' with something I'm already good at or have experience in so that it's a short desert, or not really a desert at all?
3. Have I really evaluated and decided this is the right desert to enter?
There is such a thing as overanalyzing and sometimes you need to just jump in, but I think if you're like me, you could use to take that jump less often...and when you do take the jump, make sure you've done the proper calculations.
Final note: deserts are important. They keep pursuits from being overpopulated, and when you get through one, the rewards are fantastic.
You need to chart new territory, just don't always be charting only new territories or eventually you're going to dry up and die!!
Seth Godin calls these deserts 'the dip'.
Bruce Wilkinson uses the story of the Jewish people in the Old Testament as a template of this process in his book The Dream Giver.