Machiavelli’s Advice for Nice Guys

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 or 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 clickbait. 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.

This was why he wrote the book for which we know him today, The Prince, a short deeply original manual of advice for well-disposed princes on how not to finish last. And the answer, in short, was 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 counter-productive obsession with acting nicely originated from: 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 wound up as the king of kings and the ruler of eternity.

But Machiavelli pointed out an inconvenient detail to this sentimental tale of the triumph of goodness through meekness. From a practical perspective, Jesus’s 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.

And so, proposed Machiavelli, the secret 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, the CEO, political activist or thinker – should learn every lesson from the slickest, 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 demagogue; the earnest entrepreneur from the trickster.

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 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 simply nobly intentioned. It is not enough to dream well: the true measure is what we achieve. The point is to change the world for the better, not reside in the quiet comfort 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 are 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.