The clue is when you spend more time sitting on your ass reading and/or surfing the web/newgroups then you do in applying what you know and gainning some real experience.Where and how do You prioritize your time? When is enough, enough? Did you reach a breaking point? What were the clues?
The breaking point is when your too damn lazy to go and try to learn, use, and master the skills of the current gear you have before you think you need to go and buy something else.
I see it everyday in every newsgroup I come across. Nobody takes the the time learn, or understand the basics and then apply them to gain experience. Everyone wants the quick fix, the shortcuts, the easy and lazy method, to be like a monkey and copy what someone else has done not knowing or understanding how or why. The other half spends too much time on the technical things most of which that make very little difference. They hold back or won't do something or use something in fear it is not going to be perfect or even close to perfect.
At least 85% of the questions that get asked that I see could be answered by those that ask them, and in the same time or less it takes to answer them if they only took the time to really think it out or to try it themselves. While they may not get the exact answer, they would at least come back to ask an intelligent question with the experience and proper context to learn something of real vlaue they could use to get them at least one step further.