Cautious, circumspect, wary, chary, calculating are comparable when meaning prudently attentive to the dangers one may encounter or the risks one may face, or revealing such attentiveness. The same differences in implications and connotations are apparent in the nouns caution, circumspection, wariness, chariness, calculation when they denote the quality of the character or the mental processes of one who is so attentive.
Cautious and caution usually imply both the prompting of fear, especially of fear of failure or of harm to oneself or others, and the exercise of forethought in planning or of prudence in proceeding so that the dangers of failure or the risks of disaster may be avoided or minimized.
Circumspect and circumspection frequently imply less fear than cautious and caution; commonly, however, they suggest the exercise of great prudence and discretion, especially in making decisions or in acting, and the surveying of all possible consequences, lest moral, social, business, or political harm may inadvertently occur.
Wary and wariness usually carry a far stronger suggestion of suspiciousness than cautious and caution and sometimes, as a result, connote less well-grounded fear. Often, also, the terms imply alertness in watching out for difficulties or dangers or cunning in escaping them.
Chary and chariness imply the cautiousness of those who are careful of what they have or what they can give, say, or do and proceed with great reserve or discretion.
Calculating and calculation imply the caution of one who carefully and deliberately plans the way to attain his own and often selfish end taking into account every possible danger and the way in which it can be met.