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I am not a psychologist so forgive the dumb question. I frequently read the "calculating" sign attributed to people with anti-social behavior like psychopaths, but I fail to understand what this word exactly mean. According to Merriam-Webster, calculating is "marked by prudent analysis or by shrewd consideration of self-interest". However, I am not sure I understand what exactly is bad about this. Surely we are all better off doing some prudent analysis about the situations we are in, no? Would you just jump into a job without analyzing whether it is good for you or not? How about when you decide to get married, do you just jump into a marriage without thinking about the possibility of the success of the marriage? Perhaps the second part of the definition is negative, I mean the "self-interest" part, but then this sounds like being selfish, as opposed to how this word is commonly attributed to antisocial or even criminal behaviour.

Looking at it differently, the opposite of the definition above is perhaps "marked by no analysis and consideration of self-interest." Now yes, the second part seems altruistic, but the first part is something that no one would want.

I am sure I am missing the obvious, perhaps it is because English is not my main language, so I would appreciate some explanation on this word from a psychology perspective.

Thanks

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    $\begingroup$ Oscar Wilde put it very well in one of his 'priceless' aphorisms: A calculating man is "someone who knows the price of everything and the value of nothing." Of course this assumes you know and understand the value of having values. $\endgroup$ – Mozibur Ullah Jul 15 '20 at 21:31
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The thesaurus may assist. The Synonyms of 'calculating' are: artful, astute, calculative, canny, conniving, crafty, cunning, deceitful, devious, dexterous, dirty, disingenuous, foxy, guileful, machiavellian, manipulative, scheming, shrewd, slick, slippery, sly, subtle, underhand, unscrupulous, and wily.

Acknowledging that everyone pursues self-interest to an extent, the intent of the definition appears to suggest that a 'calculating' person has little empathy or consideration of others.

Synonyms extracted from Merriam-Webster and Oxford.

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