Spiritual Cartography for the Chronically Despairing
Mapping Despair with Kierkegaard, Dante, and a Broken Compass
Lately I’ve been thinking a lot about Dante's Inferno.
I am not sure why – Perhaps the 24-hour news cycle featuring a new circle of Hell every hour or the stories of innocent men being ferried off irretrievably to some dark hole. Whatever the case, the opening lines of this poem have been rolling around my head like an existentially angsty pop song:
"Midway in our life's journey, I went astray from the straight road and woke to find myself alone in a dark wood."
There are many variations of it, some say he was “awakened in a wood” or “woke” to find himself in a wood, while others just say, he “came to find himself,” which sounds less dramatic. Nonetheless, they all seem to mean the same thing, but I really am drawn to this idea of “waking” or “finding myself” in a dark place.
At first, I would imagine someone wandering aimlessly like a tourist in a new city stumbling into a park and waking up in a forest, but as I thought about it, I now see it differently, I think he was always in the dark forest and is now just waking up to it. That’s probably the wrong way to read it, but I like to think of it this way, because it seems more familiar to me.
Have you ever had that experience?
You turn on the news and wonder, “What world is this?” “How did we get here?” Or maybe it’s a bit more personal, you wipe the condensation off the bathroom mirror and you don’t recognize the person looking back at you? You wake up to the stress on your face , the self-harm on your body, the lostness in your eyes? Your world seems so foreign – work isn’t what it was or what you thought it could be, you don’t recognize the look in your partner’s eyes anymore, “What happened to us?” you mutter, as you look around the room at all that you’ve accumulated.
You are waking up to the darkness. And as each day passes, you recognize that the straight path you were on is long gone. You’ve lost that path and maybe by virtue of that, you find yourself waking up in a place that feels like Hell.
Welcome to despair.
“Abandon all hope, ye who enter here” (Canto III, line 9)
Dante’s writing is beautiful, dramatic, and masterfully weaved together. He offers a clear picture of the soul’s journey through despair and offers us a map of the geography and the topography of suffering. He shows us the literal circles of hell complete with rivers, and cities, and other obstacles.
But, what good is a realistic map of a fictional place?
Nothing – That is – Until you realize that these Nine Circles are not beneath us, but around us—in places like city councils, courtrooms, shelters, and phone screens.
We are lost in a dark wood and the straight path is out of sight.
Enter Kierkegaard
Six hundred years after Dante, Søren Kierkegaard, the father of existentialism, also wrote about despair. If Dante gave us a map then Kierkegaard gave us an x-ray. He went beyond the outer contours of despair and focused on the inner states.
He was interested in the part of the self that wants to be more than just a collection of impulses and inherited beliefs; so his focus was different from Dante in that his aim was less on the characteristics of despair and more on the human estrangement that fueled it. Estrangement from God – The source of creation - and estrangement from one’s own depths - the place God resides.
In his book, The Sickness Unto Death he presents one of the most piercing ideas in modern thought: that despair is not a mood. It is a condition. A misrelation. A sickness of the self. Soren offered three types of despair, each representing a “waking up” or an increase in the awareness and consciousness of the person, and each demonstrating despair as a misalignment of the self.
The First Type: The Sleepwalker (Despair of Not Being Conscious of Having a Self)
Imagine a man walking through Times Square, scrolling TikTok as he dodges yellow cabs. He laughs. He eats. He drinks. He lives for likes and dopamine, but somewhere in him is an ache he can't name. Kierkegaard calls this the despair of not knowing you are in despair—the despair of not being conscious of having a self.
It’s not dramatic. It’s subtle. A life of quiet disconnection.
Disconnected from anything sacred. Disconnected from the self. Disconnected from others.
Sleepwalkers can be seen as your typical high-functioning addicted person, who can hold a job and manage all the day to day obligations, but when it comes to silence they feel overwhelmed. They try to drown away as much of their life as possible with sensation, drugs, alcohol, sex, gaming, pornography, work.. anything to avoid the monotony of being awake.
They fear silence, lack an internal compass and are missing a sense of self to anchor themselves. Instead, what they have are habits, deadlines, and noise.
In Inferno, Dante would put these souls in the upper circles of Hell—lustful, gluttonous, greedy. Not evil, exactly. Just... asleep. They're blown around by passions like leaves in the wind. They never made deep contact with themselves, or the divine. They followed instinct, culture, habit. Spiritually unaware. They’re caught in storms, mud, fire—external chaos reflecting internal confusion. Their lives were shaped not by cruelty but by avoidance.
It’s not punishment that defines these circles—it’s absence. These souls don’t burn. They drift.
The Second Type: The Runaway (Despair of Not Wanting to Be Oneself)
This is the soul that wakes up and screams. It knows that the world is on fire and that their very soul clamors for something more, but they don’t want or can’t face it. This is the despair of not wanting to be oneself. A man looks in the mirror and sees a failure. A woman buries her shame in overwork or addiction. It’s despair rooted in self-rejection, often masked as ambition or compliance.
Runaways are running from themselves and the world destined for them. They seek to be “good” and “special” and anything they feel they are not. They deny their desires and hopes and dreams. They are overwhelmed by the tyranny of self-improvement and shame infects their every emotion like a malicious virus.
In Dante’s descent, this brings us to Circles Six and Seven—heresy and violence. Heretics, in Dante’s world, denied the immortality of the soul. They tried to erase the part of themselves that transcends death. They literally refused to believe in the self as a divine creation.
Violent souls follow. Some rage against others. Some, like suicides, rage against themselves. Their suffering is not just the act—they suffer the logic of their despair: “I cannot bear to be this self.”
Kierkegaard writes that this is a form of weakness, but it’s not mild. It’s tragic. It’s the pain of being a soul who can’t carry itself.
The Third Type: The Architect (Despair of Wanting to Be Oneself in Defiance)
This person isn’t asleep in the dark woods—they’ve unpacked, pitched a tent, and started designing a dream house. They reject the idea that the self might be grounded in something larger, relational, or sacred. They see the suffering in the world and hear the longing in their souls, but instead, they choose to become the sole architect of their reality and their identity, which isn’t in itself a bad thing, except that this is willful self-creation in rebellion, so regardless of what their heart is saying, what the world might need around them, how their values are leading them, or what they know to be their heart’s longing, they choose the narcissistic way.
They are not led purely by arrogance, exactly. It is something colder. A defensive autonomy. The belief that, through enough insight or accomplishment, you can outgrow the vulnerability of being human.
This is Kierkegaard’s third despair: the despair of wanting to be oneself—in defiance. It is the soul who sees its finitude and declares it a flaw. Who builds a fortress of mastery and calls it freedom.
Dante places these souls in the lowest circles. Here are the deceivers, the betrayers, the calculated architects of destruction. Not because they lack intelligence, but because they use it to sever themselves from truth and grace.
Lucifer, frozen at the bottom of Hell, is the purest image of this despair. He does not burn. He does not scream. He is immobilized by his own refusal to yield. His wings flap forever, not in freedom, but in a wind that chills the entire pit.
Architects build a cathedral of competence to protect a vulnerable human being who refuses to be touched. Who fear grace because it would mean needing something beyond themselves. The more tightly one clings to the self-made identity, the more one is haunted by its contingency and its loneliness. The more control they seek, the more terrified they become of surrender. It’s a kind of spiritual perfectionism: “I’ll be my own source. I’ll make myself worthy. I’ll decide who I am, thank you very much.” And yet, deep beneath the surface, there’s often a gnawing fear: What if I’m not enough? What if this image I’ve built isn’t real? That’s the ache of the third despair.
That is the hell of pride. The trap of control.
This is the climax of self-reliance taken too far. The soul becomes a closed system.
So, what do we do with despair?
According to Dante and Soren - Despair is not reserved for the obviously broken. It is the condition of any soul who misrelates to itself.
Some despair without knowing.
Some despair by running from themselves.
Some despair by doubling down and declaring independence.
All of them are lost.
But neither Dante nor Kierkegaard leaves us there. In The Divine Comedy, Dante eventually ascends. He passes through Purgatory and beholds the stars. In Kierkegaard’s vision, despair is curable—but only when the self rests transparently in the power that created it.
So, what if we took these models not as doom, but as maps?
The sleepwalker needs awakening—a moment of spiritual recognition, of saying, “There’s more to me than this.”
The runaway needs compassion—the courage to accept their wounds without being defined by them.
The architect needs surrender—to learn that autonomy is not freedom, and that grace is not weakness.
Together, Dante and Kierkegaard do not just diagnose despair. They offer a strange kind of hope: that even in the darkest woods or the deepest pits, we are never fully alone. That the map, no matter how twisted, leads not only downward—but through.
Through
There’s a moment in the Inferno when Dante, terrified by what he’s seen, is told by his guide, “You must go through it.” Not around. Not above. Through.
Despair isn’t cured by denial. Or performance. Or autonomy.
The sleepwalker must be awakened.
The runaway must be embraced.
The architect must be broken open.
We are not designed to save ourselves.
And perhaps that’s not a flaw—but the beginning of a deeper kind of healing.
Meditation - , Awaken, Embrace and Surrender
I offer the following short meditation as a practice to help you navigate your way through the dark wood.
Find a quiet space where you won’t be disturbed.
Sit in a relaxed but alert posture—feet on the floor, spine upright, hands resting in your lap.
Take three deep breaths:
Inhale through your nose, exhale through your mouth.
Then allow your breath to settle into its natural rhythm.
Close your eyes and begin to awaken—not through effort, but by gently arriving in this moment.
Feel the breath move in and out. Let it anchor you here.
When your mind wanders, simply return to the breath.
You don’t need to fix anything—just stay present and open.
Now scan your body with awareness.
Notice where you feel tension, fear, or sadness.
Breathe into those places and embrace them with kindness.
Ask yourself:
What do I need to hear right now?
What is my body asking for?
Offer yourself care—a word, an image, or the feeling of being held.
Let it remind you that you are not alone. You are worthy of compassion.
Now, surrender—
Not in defeat, but in trust.
Trust the wisdom of your loving heart.
Trust that you are being held by something vast and good.
Let go of the need to control or figure anything out.
Trust this moment. Trust yourself.
Rest here a little longer, in the presence of breath, love, and stillness.
And when you are ready,
Open your eyes.
Awaken.
About the author: Daniel Gutierrez, Ph.D., LPC, CSAC, is a Contemplative Existential Psychotherapist, Mental Health Researcher, Professor & Martial Artist.