Call someone “Machiavellian” and everyone knows what you mean: sneaky, ruthless, always three moves ahead. Not bad for a guy who died almost 500 years ago. His book The Prince asks a question straight out of a group chat: is it better to be loved or feared?

Plot twist: Machiavelli wasn’t a prince. He was a government official in Florence who lost his job when the Medici family returned to power in 1512, and the next year he was jailed and tortured on suspicion of plotting against them. Stuck on his farm afterward, he wrote The Prince, probably hoping it would get him hired again. Talk about an ambitious cover letter.

His answer, in W. K. Marriott’s translation: “it is much safer to be feared than loved, when, of the two, either must be dispensed with.” But here’s the part people skip: “a prince ought to inspire fear in such a way that, if he does not win love, he avoids hatred.” And the fastest way to be hated? Take people’s stuff, because “men more quickly forget the death of their father than the loss of their patrimony.” (Patrimony means inheritance. Dark, but he has a point.)

That twist still works today. (This is my reading, not Machiavelli’s.) Think of a strict teacher: clear, fair rules earn respect, but rules that change with the teacher’s mood breed resentment fast.

Still, Machiavelli wrote for rulers in a violent, divided Italy. Today’s leaders answer to courts, journalists, and voters. In a democracy, ruling by fear usually ends at the next election.

So here’s the test, whether you’re running a country or a student club: if people stopped being afraid of you tomorrow, would they still stick around?