While I was out with Andy and TB-1 we got to talking about a problem we see in the Jedi Community as a whole: Enabling. This is one of the primary issues that comes up when you teach people to act with compassion, but never really talk about tempering it with common sense, judgement and/or opposing action.
In the community at large, we talk about wanting to help people, being accepting of them and tolerant of their actions. At some point, doing all of this becomes detrimental to the growth of the individual you are enabling. I know I've done it, a few times, and in fact I'm even able to recognized that I was doing this when I went out to meet Master Joni in late 2007. I noticed he had a drinking problem, but kept silent about it- fortunately, as you can tell by a recent thread, he has overcome alcoholism.
In the fiction (good grief, I'm actually using the fiction for this, lol) we see that the Jedi were confident and didn't stand still when destructive behavior was being thrown directly before them (Obi-Wan: *waves hands* "You want to go home and rethink your life"; Mace Windu: "He has control of the senate and all the courts. He is too dangerous to be left alive!"). Instead, they followed what was the most logical course of action to protect those around them. In Obi-Wan's case, he kept a drug dealer out of the cantina for a day (at least). In Mace's case, he attempted to rid the galaxy of a problem which was the basis for the original trilogy.
Looking directly at the latter example, we can see how Anakin's training as a Jedi ended up destroying years of the future that no one in the SWU could ever get back. He was Palpatine's enabler, and as such became a victim to the dark side (now, there were a number of other factors, but this one cannot be overlooked as one of the major turning points in the prequels).
But this isn't the only instance were we see enabling behavior. Sometimes it is more difficult to recognize when you are enabling someone.
Episode III wrote: Yoda: Premonitions, premonitions. These visions you have... Anakin Skywalker: They are of pain, suffering. Death. Yoda: Yourself you speak of, or someone you know? Anakin Skywalker: Someone. Yoda: Close to you? Anakin Skywalker: Yes. Yoda: Careful you must be when sensing the future Anakin. The fear of loss is a path to the dark side. Anakin Skywalker: I won't let these visions come true, Master Yoda. Yoda: Death is a natural part of life. Rejoice for those around you who transform into the Force. Mourn them do not. Miss them do not. Attachment leads to jealousy. The shadow of greed that is. Anakin Skywalker: What must I do, Master Yoda? Yoda: Train yourself to let go... of everything you fear to lose.
Believe it or not, this entire conversation is Yoda enabling Anakin's fears. It's mostly because he has poor crisis communication skills. The statements are all cookie cutter, and he never really gets down to the bottom of what the problem is. Knowing that Anakin is having problems, he has kind of shoved this entire thing off to the side as an obstacle Anakin should be able to easily get over. This is his failure as a leader to understand the whole of the problem and not seeking to find someone who can further assist him.
This is all part of the arrogance of the prequel Jedi Order and their complacency.