Articles

When Frodo Failed: Why Tolkien’s Most Important Moment Isn’t Heroism, It’s Mercy 

By Mark Douglas (probably thinking about Middle-earth again), Dec 11th 2025

We tend to imagine spiritual growth as a kind of heroic ascent toward enlightenment: climb high enough, stay morally pure enough, organize your inner world enough (psychosynthesis and all that, and eventually you’ll stand at the fires of your own Mount Doom and heroically throw in whatever Ring you’ve been carrying. Oh, and btw, I promise there's some astrology in here, way down below near the end.

But back to the hero's journey: Except that’s not how it works.

And Tolkien, bless him, refuses to flatter us with a comforting myth of moral mastery. Because the truth, a truth many of us don’t want to admit, is this:

“Frodo failed. Completely. Catastrophically. And the world was saved anyway.” He screwed up and didn't destroy the ring.

Tolkien once said that this “complete failure” is the most moving point of the tale. Because The Lord of the Rings is not a story about heroic self-reliance. It’s a story about mercy.

Let me unpack that (with a coffee in hand, because this is one of the great theological treasures hidden in pop culture and I didn't see it until a big week of working through my theology studies, and getting into Hauerwas and Christian ethics).

When Frodo reaches the Crack of Doom, he does not triumph. He does not marshal inner strength. He does not “remember who he is” like a Disney protagonist - there’s no Elsa belting a power ballad and suddenly mastering her inner chaos. No Ted Talk, either. That’s not ambiguity. That’s collapse. 

Frodo fails at the very moment he was meant to succeed. And Tolkien intended this. He didn’t want a tidy victory. He wanted the truth about the human condition: even our strongest virtues eventually reach their limits. We do not save ourselves by being perfect.

Interlude Time: Frodo’s Failure and the Paradox of Psychosynthesis

There’s a beautiful paradox tucked inside Frodo’s collapse, especially if you work with psychosynthesis, where the Will is the central integrative force of the psyche. Assagioli called it “the inner power that directs and regulates all the other functions.” The Will gives direction, coherence, and meaning. So how does Frodo’s utter failure of will at Mount Doom square with a psychological model that treats the Will as essential?

Surprisingly, it fits perfectly.

When Frodo says, “I do not choose now to do what I came to do,” it is not just moral exhaustion. It is the collapse of the personal will — the everyday will of the personality, the conscious “I” that tries to act, decide, choose, and persevere. Frodo’s personal will is spent. Burned out. Possessed by a Symbol far too powerful for any human psyche to withstand. In psychosynthesis terms, this is predictable: the personal will eventually reaches the end of its capacity.

And here's the rub:

Frodo’s failure is not the failure of Will. It's the failure of one layer of will, and the revelation of another.

Long before Frodo reaches Mount Doom, a deeper Will is already moving through the story: the mercy Bilbo showed Gollum; the mercy Frodo repeated; the pity Gandalf insisted upon; Sam’s almost impossible fidelity; the Fellowship’s protection; the odd “chance” turnings Tolkien calls a “guiding purpose.” All of these are not random. They are signs of what psychosynthesis calls the Transpersonal Will,  the Will of the deeper Self (capital-S), which acts through relationships, events, intuition, and surprising turns of fate. 

Frodo’s personal will fails.
But his earlier alignments with mercy allow the transpersonal Will to complete the task without him.

This is classic psychosynthesis:
The personality acts faithfully in small ways, the deeper Self carries the larger arc. Those outer planets, fixed stars stuff: Neptune- Uranus, Pluto that have a way of cracking us, like a dad crashing out fixing a hallway light fixture.

Grace moves through the cracks.

Assagioli said that the first act of the personal will is recognizing its limits. Frodo recognizes his limits through failure, and that failure becomes the very opening through which salvation enters. Gollum, the shadow-self, becomes the instrument of the Will that Frodo can no longer carry.

So the paradox resolves beautifully:

“Heroic willpower collapses.
Syntonic Will - the Will aligned with mercy, succeeds.”

In psychosynthesis, this isn’t defeat. It’s cooperation. Syntonic is a harmonizing of ego and transpersonal -- that this isn't simple meaningless suffering or losses, or collapse. Faith and trust stuff.

It’s the handoff between the ego’s strength and the soul’s movement.

And that’s exactly what happens at the edge of the fire.

If Frodo succeeded by willpower, the story becomes a lie, a moral self-help parable where discipline defeats demons, purity repels evil, and effort guarantees victory. Tolkien: devout Catholic, lover of subtle grace, laughs quietly in the background. Because he knows the deeper truth:

“We don’t win because we’re strong. We are carried by mercy.”

Gollum becomes the unlikely apostle of that mercy. The Ring is destroyed only because Frodo and Bilbo both chose mercy over necessity. Bilbo spares Gollum. Frodo spares Gollum. Sam, God bless him, nearly fails to, but even that tiny restraint matters. If they had done the “practical” thing and killed him, Middle-earth would have burned.

Acts of mercy ripple forward in ways we cannot predict. Sometimes the person we saved becomes the instrument of our own salvation. Heroism gives you control. Mercy gives the big cheese, God, space to act.

Tolkien even gives us a word for the moment when grace crashes through tragedy: eucatastrophe: the sudden happy turn when all seems lost. And that’s exactly what happens at Mount Doom: Frodo collapses. Gollum attacks. Gollum falls. The Ring is destroyed. Salvation arrives sideways, unexpectedly, beautifully.

This isn’t motivational positivity. It’s a spiritual worldview: grace is not the reward of heroism, grace is what happens when heroism fails. You don't receive grace because you are good -- you receive it because the great gardener above, is good.

Most of us carry Rings: burdens, traumas, responsibilities, family histories, leadership decisions, the weight of expectations, the “I must fix everything” mindset. And like Frodo, we have moments where we falter, hit our limits, or don’t live up to the ideal.

Here’s the liberating truth Tolkien gifts us:

“You are not the saviour of the world. Grace does not depend on your perfection. And mercy is stronger than your collapse.”

That’s why Frodo’s failure is the emotional heart of the story, because it is our story too.

Strip it all down, and Tolkien’s point is profoundly spiritual: the world isn’t held together by flawless people. It’s held together by compassion, humility, forgiveness, and mercy. Even our failures can be gathered into a larger redemptive tapestry. There’s a quiet glory in that.

We are invited not to heroic perfection, but to mercy, humility, and letting grace work through the cracks. The sea within us is not mastered by force. It is healed by gentleness.

And if you remember nothing else, remember this:

Frodo failed. And love still won. Which means you are freer than you think.

And that, truly, is eucatastrophe at its finest.

What does this have to do with birth charts? Plenty -- in my next article, I'll carry this forward. Thank you for reading! Mark

A riff on Spencer Thompson’s 2025 Kenarchy Journal essay

My own life, probably like yours, mirrors the vexing issue of finding some bliss between order and chaos. This fall I'm doing a two-week pilgrimage and peace studies study in Northern Ireland, Scotland, ending in St Cuthbert's on the holy island in Lindisfarne Northumbria.  I can relax and find the flow then.... except.. our professor was adamant that "the pilgrimage starts now!" And as things do, this article from Kenarchy journal found its way to me and challenged me to have a look at my own life, my own chaos, and work towards reconciling some flow. Not then, not in some distant future, but here and now in the tension of this chaotic lead-up.

The Corporate Hustle Meets Vacation Time

You work your corporate job all year, powering through spreadsheets, strategy decks, and passive-aggressive email threads, all for that one promised week: the vacation.

It’s curated with Virgoan precision—
Flights timed to the minute.
Hotel booked six months in advance.
Dinner reservations locked in with Yelp-based zeal.

This time, you think, nothing will go wrong.

And then it rains.
Your Uber doesn’t show.
The "quiet" Airbnb is above a jazz club.

Now what? Is this chaos? A cosmic joke? Or—more scandalously—is it exactly what you needed?

Spencer Thompson’s “The Great Music” begins with that same tension.
Modern life has become a grand, meticulous system trying to eliminate chaos—yet ironically, it feels more chaotic than ever. The harder we grip for control, the more meaning slips through our fingers.

We mistake order for harmony and chaos for discord, but Thompson argues it’s not that simple. In truth, harmony only exists where order and chaos meet. It’s not a matter of eliminating the mess—it’s about learning to live with it, even love it.

That’s what the Genesis story actually tells us (once you peel it back from its empire-friendly packaging): before God ever says “Let there be light,” the Spirit hovers over the deep—the ancient symbol of chaos. Not to destroy it. To create with it. How Pisces/Virgo axis.

Enter Tolkien.

In The Silmarillion, Tolkien’s divine beings create the world through collaborative music. But one of them—Melkor—tries to hijack the melody. His discord threatens the whole composition… until the Divine doesn’t strike him down, but instead folds the dissonance into an even deeper harmony.

That’s the big reveal:
Love—not control—is what redeems the music.

And this isn’t just fantasy. It’s the beating heart of the gospel, and it's the beating heart of psychosynthesis coaching.

Agapē, the New Testament’s word for self-giving love, is the force that binds all things together in perfect harmony (Colossians 3:14). It doesn’t run from mess—it embraces it, transforms it, includes it.

As Martin Luther King Jr. said:

“Love is the only force capable of transforming an enemy into a friend.”

So when your trip—or your life—falls apart, maybe it’s not failure.
Maybe it’s the invitation to a richer song.

The goal isn’t perfect conditions. It’s music.
And music needs wild notes, too.

Mark Douglas, June 2025