Dante & the Archetypal Journey of Becoming One’s Best Self

The opening lines of Dante’s Comedy are so direct, so chilling.

In the middle of the journey of our life,

I woke to find myself in a dark wood,

Where the straight road was lost.

We’re right beside Dante as he becomes aware of the deep ravine and ominous forest, as hope flares with a glimpse of sunshine on a hilltop, and then as despair reclaims him: the way uphill is blocked by a leopard, a lion, and a gaunt, hungry wolf. They drive him deeper and deeper into the dark ravine. It’s the stuff of nightmares.

Though rescue does appear, it’s not a knight to slay those beasts. Instead, a ghostly figure materializes out of the gloom—the Roman poet Virgil—who speaks in a voice rusty with disuse. And the news Virgil delivers is not quite what the lost traveler might have hoped for. Dante, he says, can’t reach the sunshine directly—and not anytime soon. He’s going to have to go the long way around, spiraling down through Hell, and up the mountain of Purgatory. At the top, his old love, Beatrice, will guide him still farther upwards.

Along the path, there are mythological beasts (the three-headed dog-beast Cerberus, the bull-headed Minotaur, the Medusa with her snaky hair), and there’s a just-in-the-nick-of-time escape from demons (with pitchforks to keep the grafters sunk in boiling tar) who try to capture Dante—a reference to the accusation that got him exiled from Florence. It’s fun to puzzle out the metaphor behind the punishment of each sin: it’s obvious why murderers boil in a river of blood, but why do gluttons wallow in mud while the evil counselors are encased in tongues of flame? Why do the archbishops who took bribes land upside down in baptismal fonts and the treasonous end up enveloped in ice?

The farther down Dante goes, the darker Hell gets, the heavier the weight of human error and sorrow. And at the very bottom—at the center of the world, is Satan, trapped in a lake of ice, chewing sinners in his three grotesque mouths.

But the moments I like best are the moments when Dante doesn’t just observe but feels. This trip isn’t an abstract lesson to him; it’s a journey of the heart. As Dante spirals down through the nine circles of Hell, he’s reviewing his life and choices—some of which got him trapped in that dark wood and sent on this journey. Dante faints when he sees the adulterous Francesca whirling around with her lover Paolo—people of his own generation, bloodily murdered by Francesca’s husband. (That could have been him, after all. Beatrice, whom he’d loved, was married, as was Dante himself.) Further down in Hell, after escaping the demons, he and Virgil slide down into the pit of the Hypocrites and walk among the lead-cloaked figures. (That’s a nice way of acknowledging that those two, like most adults, must have occasionally preached better than they practiced.) And at the bottom, he crawls along Satan’s hairy, greasy torso to reach the center of the Earth and start the climb upwards.

The theology of the afterlife in the Comedy always offended me. Even though Dante insists that any sin may be forgiven if it is repented before death, eternal suffering really doesn’t seem like a fair consequence for choices made during a single lifetime. (I love how intelligently The Good Place handled that problem in its last season.) It was always the spiritual journey that moved me, and that journey is told through big, archetypal metaphors. As one book of criticism suggests, Dante travels From Dark Wood to White Rose.

Yet the Comedy doesn’t quite line up with the Hero’s Journey, at least not in the narrow sense. Although the poetic power of the Comedy does rely partly on the big archetypes of a journey, Dante is more than Luke Skywalker. Yes, he goes down into a cave of darkness, faces his fears, learns who he is, and rises back up into the light. On the other hand, though he encounters monsters, he doesn’t defeat them in combat. (When the Inferno was transformed into a video game, Dante became a knight-errant slashing his way through Hell to rescue his girlfriend. Sigh.) Dante’s is a journey of understanding, a spiritual education. He is guided by Virgil the whole way. (Allegorically, Virgil signifies a heart-filled reasonableness or creative intelligence. Brenee Brown might call him a figure for Whole-Hearted Living.)

While Dante always moves forward, the sinners are stuck—trapped inside the stories they tell themselves. And what a wonderful insight that is! (Maybe it’s not so surprising that George Saunders uses essentially the same metaphor for the dead in the cemetery of Lincoln in the Bardo.)

It’s lovely to emerge with Dante out of Hell, with its smoke and filth and stench, into the fresh air and clear light just before dawn. And the next part of the Comedy, in which Dante and Virgil climb laboriously up the mountain of Purgatory, is my favorite section. Level by level, the dead erase their sins while they learn new habits of thought and behavior. They go up: the aim is not punishment but healing. In fact, the mountain is an upside-down mirror of Hell—made of the dirt shoved aside when Satan fell into Hell. What Dante has witnessed in Hell, he now has to internalize.

Since I taught at a therapeutic boarding school, I urged my students to read the poem in the light of their own difficult journeys towards their best selves. All of them had wound up at the school because of patterns they couldn’t break: addiction to drugs or the internet, crippling anxiety, anger that scorched everything in its path. So every year, when I taught the newer students a class on “Crimes and Punishments,” I encouraged them to write a dream-journey imitating Dante’s. The key stipulations were three: the writers had, like Dante, to be both the narrator and the traveler; the journey had to reflect them back to themselves in a helpful way; and they had to choose a guide or companion. (After all, the unofficial motto of the school was “You alone can do it, but you can’t do it alone.” They were learning how to have healthy relationships, with boundaries and trust.)

Every year, I was astonished and moved by the results—elaborate and vivid narratives of intelligent self-reflection, often twenty pages or so. The students’ process moved me even more. They worked with me and a clinician to identify which habits were stymying their growth or why they had such a hard time envisioning a positive outcome. Sometimes they made real breakthroughs; sometimes they posed themselves questions that couldn’t yet be answered. Either way, it was a glorious experience—teaching at its most satisfying, involving the whole person.

And however the writing assignment turned out, they were learning to read with their hearts as well as their heads…