aspiration / contentment

i've been thinking about this for a while. How aspiration and discontent are really 2 sides of the same coin. Wanting more. At what point in life does one decide to just settle for what one already has, do the finding pleasure in the small things thing, and stop seeking for more and better? i mean, contentment is a good thing, i think. i'm not knocking contentment. i just find it disturbing that some people seem to have this way of wanting to squelch all desire for more in others by reprimanding them for discontentment.
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It all depends on what label we fix on things, doesn't it? Call it aspiration, and it looks really good. Call it discontentment, and suddenly it's something blame-worthy and wrong.
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At what point does one just decide (if it's even a decision in the first place...?) that one's present reality is not what one wants to remain in for the rest of one's life, that it's time to try, at least try, to move on?
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i'm not unhappy with the way things are now. In fact it's all rather comfortable -- the pain of marking bad writing asides. (And this pain is considerable...) i just wonder if perhaps i should be doing something else. Something different, if not more.
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Also, there's something to be said, i think, for experience. i've been in this place before: of feeling that where i am, or what i'm doing, is not right for me, and wanting to move to something else, looking for something else. And being told in various ways and by various people-who-think-they-are-being-helpful that the problem lies with me, with my perspective on things. And i moved anyway. And the move made all the difference.
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i think, this tendency to pronounce quick judgement on someone else's experience -- betrays, to me at least, a lack of trust in that other person's ability to discern the quality of their own experiences. Sometimes i feel like saying to some of these people-who-think-they-are-being-helpful, "Give me some credit, can? i'm not that stupid..."
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