It takes a long time to deeply learn your tools. Switching means starting over. One of the hardest things in any trade is knowing when upgrading your tools is worth throwing away that experience and how much better they have to be to compensate for the initial drop in productivity.
Hackers are optimists; managers are pessimists. We tend to err on the side of cool toys; they tend to err on the side of avoiding catastrophe.
But if you don't sit down to learn, you will never learn. You will fall into a chicken - egg trap. You will not use a new tool because you don't know if it is any better, and you will not know if it is any better because you did not use it. How to break the cycle?
By the way, it DOES take a long time to deeply learn your tools, but it takes a very short time to learn them enough to reach the same level of productivity than the older one, unless it is a complete shift of paradigm. This is specially true when you are moving to newer versions of the same programs, as long as some backward compatibility is kept, you will be not starting from scratch.
Hackers are optimists; managers are pessimists. We tend to err on the side of cool toys; they tend to err on the side of avoiding catastrophe.