This article is part of a series entitled Machiavelli in Society. See also:
Perhaps last among the things we associate with care, love, and respect for others is calculativeness, of the sort that once led Machiavelli to famously write, “And a prince ought, above all things, always endeavor in every action to gain for himself the reputation of being a great and remarkable man.”  Machiavelli finishes this chapter with a claim with which we’re perhaps more disposed to agree. “[I]f everything is considered carefully,” he argues, “it will be found that something… which looks like vice, yet followed brings him security and prosperity.” 
I’ll take Machiavelli at his word. I’ll argue that calculativeness, in the abstract, can help us attain diverse and positive ends, like empathy — in the simple sense that, well, empathy can be worked on. Why can’t we train our cognitive and emotional apparatus towards the deepening of our immersion into other peoples’ lives?
Separating Method from Content
A social interaction pattern’s tools and strategies may be separated from the intended ends of those tools and strategies.
Can we separate a social behavior pattern’s abstract approach to evaluating challenges, setting goals, and making decisions from the specific content of these challenges, goals, and decisions? I’ll call the former its method and the latter its content, and I’ll argue that we can.
Let’s explore the dependency between method and content. They can be studied independently. Can they be chosen independently? That is, if we adopt a particular method, may we still freely choose our content?
Certain methods might lead irrevocably to certain contents. If we abstractly decided, for example, that social interaction is organic and unfit for modification, then, well, we’d be forced to accept whichever social tendencies organically arose in us.
Other methods, though, (e.g., the one whereby social behavior can be studied) can be used to pursue any contents (e.g, the one whereby empathic connections are made). These special methods – say, versatile methods – may be meaningfully extracted from ideological commitment. They may be independently studied. They may be independently used.
The calculative method
Calculativeness is a ‘versatile method’.
Consider the approach to social interaction which dictates that it can be studied, practiced, and improved. I’ll refer to this abstract method as calculativeness. I claim that the calculative method can be applied to any content.
If calculativeness is a versatile method, why do we see it so often paired with destructiveness? In psychopaths, a lack of empathy often leads to both an inability to interact organically (calculativeness) and an unwillingness to act cooperatively (destructiveness). In healthy people, though, phenomena other than lack of empathy can bring about calculatedness, and the destructiveness need not follow. The observed association – between calculatedness and destructiveness – more reflects an accidental contingency of psychopaths than an ingrained non-versatility of calculatedness.
Is calculativeness is a versatile method, why do we associate it so reluctantly with empathy? Here I must refute the tempting proposition that empathy is untouchably organic. Empathy appears organic because it operates upon forces below our conscious reason. We don’t know how or why we connect with people, or feel sorry for them, or laugh and celebrate with them. We just do. Reason is absent from these processes. How can it help us strengthen them? Reason can direct us to act in ways which foster the ability of our subconscious to more properly function. Reason can tell us to pause, reflect, and meditate; reason can tell us to speak clearly and to sit up straight; reason can tell us to look the speaker in the eyes. Reason can determine our subconscious’ operating conditions. The subconscious will take care of the rest.
Calculating Stronger Empathy
Where calculated empathy can take us.
Calculated empathy offers a keen, reflective awareness of other people. We’ll direct our rational faculties to the understanding of others’ situations and needs. We’ll work to improve or own ability to convey complex emotions. We’ll take pains to present ourselves respectfully, properly, and endearingly. We’ll connect to others.
In job interviews, calculated empathy permits us to convey poise and intelligence to our interviewer. In relationships, calculated empathy permits us to appreciate the subtle dynamics of our romantic partner. Alone, calculated empathy brings us to deeper emotional intelligence. These are the fruits of calculated empathy.
The deepest insight of all, though, is that social behavior can be enriched. A neglect of this fact leaves us scarcely past the psychopath. Indeed, the psychopath’s failure lies precisely in his unthinking acceptance of social behavior. The psychopath’s neglect condemns him to destructiveness. Our neglect, though, could condemn us to obliviousness. Our interaction with others is an invaluable part of our identity. Let’s take responsibility for it.