The Devil’s War on Humility
Screwtape and the Inward Spiral of Self
We live in a culture obsessed with self-esteem. You’re told to silence negative self-talk, speak affirmations over your reflection, and rediscover how awesome you are. The world says if we just think highly enough of ourselves, we’ll finally be whole. But there’s a sinister twist here, and The Screwtape Letters exposes it brilliantly. In his fourteenth letter, Screwtape is livid, his human subject is becoming humble, and it terrifies him.
That may surprise you. The devils, according to Screwtape, don’t fear big spiritual declarations or even extravagant resolutions of moral reform. What they dread is daily dependence. The patient no longer makes grand, confident promises about holiness. Instead, he simply hopes for a daily portion of grace to endure the hour’s temptations. This posture, the humble reliance on God moment by moment, is, in Screwtape’s own words, “very bad.”
Pride in Disguise
So how do the devils respond when someone actually starts becoming humble? Screwtape’s advice is hilariously tragic: make the man aware of his humility. Let him sit back and reflect: “By Jove! I’m being humble!” And just like that, pride rears its head, not despite humility, but through it. Worse still, if the man senses this trap and tries to kill the pride, tempt him to become proud of his attempt to kill the pride. Round and round it goes.
The only safeguard? A sense of humor and a right sense of proportion. Screwtape warns Wormwood not to play this game too long, lest the man laugh at the absurdity of it all and go to bed at peace. Sometimes, freedom from the enemy’s traps looks like smiling at our own foolishness. The devil hates a Christian who doesn’t take himself too seriously.
Twisting the Virtues
But Screwtape has other strategies. The ultimate goal is to turn the man’s gaze inward. God wants virtues to open us up toward him and toward others. The devils try to hijack even humility by making it all about you. Self-contempt becomes fertile ground for cynicism, cruelty, and gloom. The man might seem humble, but it’s really just pride wearing a frown.
That’s why Screwtape wants us to equate humility with self-hatred. Got beauty? Pretend you’re ugly. Got brains? Pretend you’re dumb. But what happens when you know deep down that you’re actually not those things? Now you’re stuck trying to believe something you know isn’t true, and you’ve walked straight into the enemy’s trap.
God, by contrast, wants us to see clearly. He wants the architect who designs the best cathedral in the world to know it’s the best, and then rejoice that such beauty exists, regardless of who made it. That’s real humility. To delight in beauty, in talent, and in goodness as if they were a sunrise or a waterfall, even when they come from your own hands. To enjoy what is good without thinking more-or-less of yourself because of it.
A New Kind of Self-Love
Screwtape acknowledges a painful truth about God’s strategy: God wants to kill our self-centered animal love, but only so he can give us something better. Over time, God restores a new kind of self-love, one that delights in the self the way it delights in a neighbor. When Jesus says “love your neighbor as yourself,” he also implies that it’s possible to love yourself rightly, not through pride, but through gratitude.
The real problem isn’t self-esteem or self-loathing. It’s self-obsession. God isn’t trying to get us to think poorly of ourselves; he’s trying to get us to think less about ourselves altogether. The devils, on the other hand, are doing everything they can to keep our eyes glued to our reflection, whether in praise or in disgust. Even with our sins, Screwtape says, the Enemy wants us to repent and move on. The devils want us to wallow.
In the end, even positive self-talk is a trap if it keeps our gaze inward. God’s command is not simply, “Be nicer to yourself.” It’s this: “Die to self, and live to Christ.” That means forgetting yourself, losing your life in service to others, and finding that in Christ, you are actually more yourself than ever before.
So no, humility isn’t thinking less of yourself. It’s not thinking more of yourself either. It’s thinking of yourself less, because your mind and heart are finally filled with something better.