I will start this off by saying that ANYONE who wants to get into business for themselves must learn very quickly to move outside of their comfort zone. When you first start to do this, any tangible action will do because you are not accustomed to being uncomfortable.
Over time, your threshold for moving outside of your comfort zone will increase.
Having said that, I believe it is possible to cause damage or hurt your own success if you challenge your comfort zone recklessly. I give a prime example in my video today to at least give you something to think about.
Don’t get me wrong though. I still encourage that you err on the side of being bold over being timid. But you can still plan your comfort zone breaking activities so that they become of maximum benefit to you.
I’d like to thank John Sherry and his article at http://realsimplepeople.com/2010/07/14/do-you-have-a-big-but for inspiring me to talk about this concept. The article is well written, stock full of great lessons and hilarious to read!
Another thing to consider regarding stretching your comfort zone. From personal experience, I know that some of my best business building moments came when I was trying new things (i.e. uncomfortable things). The most successful actions were ones that came on advice from advisers. Matthew Needham wrote a great post about getting proper advice for your business here: http://bigredtomatocompany.co.uk/2010/07/why-you-need-a-consultant
If you are going to take some bold, comfort zone stretching action, consider getting some expert advice so that you are maximizing your efforts.