Machiavelli was a 16th century Florentine political thinker with powerful advice for nice people who don’t get very far. His thought pivots around a central , uncomfortable observation: that the “wicked” tend to win; and they do so because they have a huge advantage over the “good”: they are willing to act with the darkest ingenuity and cunning to further their cause. They are not held back by those rigid opponents of change: principles. They will be prepared to outright lie, twist facts, threaten, get violent. They will also, when the situation demands it, know how to seductively deceive, use charm and honeyed words, bedazzle and distract. And in this way they conquer the world. It’s routinely assumed that a large part of what it means to be a good person is that one acts well. One doesn’t only have good ends; one is committed to good means. So, if one wants a more serious world, one needs to win people over through serious argument, not click bait. If one wants a fairer world, one has to judiciously and gently try to persuade the agents of injustice to surrender willingly, not through intimidation. And if one wants people to be kind, one must show kindness to one’s enemies, not ruthlessness. It sounds splendid. But Machiavelli couldn’t overlook an incontrovertible problem: it doesn’t work. As he looked back over the history of Florence and the Italian states more generally, he observed that nice princes, statesmen, and merchants always come unstuck. That’s why he wrote the book for which we know him today: “The Prince”, a short, dazzling manual of advice for well disposed princes on how not to finish last. And the answer, in short, is to be as nice as one wished, but never to be overly devoted to acting nicely, and indeed to know how to borrow, when need be, every single trick employed by the most cynical, dastardly, unscrupulous, and nastiest people who have ever lived. Machiavelli knew where our counterproductive obsession with acting nicely originated. The West was brought up on the Christian story of Jesus of Nazareth, the very nice man from Galilee who always treated people well and wounded up as the king of kings and the ruler of eternity. But Machiavelli pointed out one inconvenient detail to this sentimental tale of the triumph of goodness through meekness: from the practical perspective Jesus’ life was an outright disaster. This gentle soul was trampled upon and humiliated, disregarded, and mocked, judged in his lifetime and outside of any divine assistance, he was one of history’s greatest losers. The clue to being effective lies in overcoming all vestiges of this story. “The Prince” was not, as is often thought, a guide to being a tyrant; it’s a guide about what nice people should learn from tyrants. It’s a book about how to be effective-not just good. It’s a book haunted by examples of the impotence of the pure. The admirable prince- and today we might add CEO, political activist, or thinker- should learn every lesson from the slickest and most devious operators around. They should know how to scare and intimidate, cajole, and bully, entrap, and beguile. The good politician needs to learn from the bad one, the earnest entrepreneur-from the slick one. We are all, ultimately, the sum of what we achieve, not, what we intend. If we care about wisdom, kindness, seriousness, and virtue, but only ever act wisely, kindly, seriously, and virtuously, we will, Machiavelli warns us, get nowhere. We need to learn lessons from an unexpected source: those we temperamentally most despise. They have the most to teach us about how to bring about the reality we yearn for, but, that they are fighting against. We need weapons of similar grade steel to theirs. Ultimately, we should care more about being effective than about being nobly intentioned. It’s now enough to dream well. The true measure is what we achieve. The purpose is to change the world for the better, not reside in the quiet comforts of good intentions and a warm heart. All this Machiavelli knew. He disturbs us for good reason because he probes us where we are at our most self serving. We tell ourselves we didn’t get there because we’re a little too pure, good, and kind. Machiavelli bracingly informs us we are stuck because we have been too short sighted to learn from those who really know: our enemies.