Transformation

The Bridge to Self: My Dark Night of the Soul

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“In the middle of the journey of our life I came to myself within a dark wood where the straight way was lost.”

— Dante Alighieri, The Divine Comedy

Some people call it the dark night of the soul.

It sounds poetic — until it’s your turn to walk through it.

Mine didn’t creep in softly. It came with thunder and fire — a season of upheaval that tore down every structure I had built:

The loss of my father The collapse of a business I had poured my soul into The breakup of my family

Each of these losses chipped away at my identity. Taken together, they dismantled it completely.

I was left staring at the mirror, not recognising the man looking back.

I couldn’t distract myself. I couldn’t fix it. I couldn’t hustle my way out.

All I could do… was feel.

The First Awakening: My Emotions Matter

This was the first lesson: My emotions matter.

They are not inconveniences to suppress, nor signs of weakness to hide.

They are messages. Indicators. Pathways to truth.

For the first time, I began to make space for my emotions — to let them rise, to let them pass, to sit with them rather than run.

I was no longer trying to skip the grief or reframe the pain with toxic positivity. I let it burn.

And in the fire, I found clarity.

As Carl Jung once said:

“One does not become enlightened by imagining figures of light, but by making the darkness conscious.”

The Inner Deconstruction: Questioning Everything

What followed was not just emotional healing — but a spiritual and intellectual deconstruction.

I began questioning everything I had taken for granted.

Not just my role in the world, but the world itself.

The system. The beliefs. The matrix we’re all born into — programmed to chase certain dreams, fear certain outcomes, and conform to invisible rules.

I devoured books — not to escape, but to understand. To find language for what I was going through.

The Four Agreements by Don Miguel Ruiz reminded me that most of what we believe about ourselves is a lie we agreed to long ago. The Courage to Be Disliked by Kishimi and Koga gave me the power to detach from the expectations of others. And The Road Less Traveled by M. Scott Peck gave me the hardest truth of all: “Life is difficult. This is a great truth, one of the greatest truths.”

These weren’t just books — they were anchors. Torches in the dark. Companions through the void.

They reminded me that this path — the road less travelled — is not easy.

It is hazardous. It tears down comforts, unsettles relationships, and opens you up to perspectives few dare entertain.

But it also gives birth to something rare: freedom.

The Worry That Follows: What About My Children?

In the midst of this inner revolution, I was still a father.

And I began to worry — not just about my future, but about the world my children were inheriting.

What beliefs were they being programmed with?

Would they be trapped in the same illusions I had to unlearn?

Would they be strong enough to walk their own road when the time came?

The helplessness of parenthood hit me hard.

I couldn’t protect them from life’s storms.

I couldn’t walk their bridge for them.

But I could prepare them.

By healing myself.

By living truthfully.

By creating a home where emotions are not feared but honoured. Where truth is valued over appearances. Where love is not control, but freedom.

The Realisation: We Are All Impermanent

As the ego dissolved, so did my illusions of legacy.

There was a time I believed I was indispensable.

That my work, my presence, my impact would echo forever.

But this journey humbled me.

The truth is: we are all shockingly temporary.

And we are far more forgettable than we like to admit.

One day, I will pop.

My name will fade.

And strangely… that’s okay.

“We are all just visitors to this time, this place. We are just passing through. Our purpose is to observe, to learn, to grow, to love… and then we return home.”

— Australian Aboriginal Proverb

It’s not being remembered that matters.

It’s being real while I’m here.

To love well.

To live fully.

To let my children see who I truly am — not just what I achieved.

A Hypothesis: The Bridge Doesn’t Have to Break You

Crossing the bridge — the dark night, the process of individuation — is terrifying.

It’s wobbly, disorienting, destabilising.

And it’s true:

Some people lose themselves on that bridge and never come back.

Others live their entire lives without ever crossing it — living for approval, driven by fear, addicted to productivity or performance.

But here’s the hypothesis I’ve come to hold:

It doesn’t have to be brutal.

Not if we take charge of the process of understanding who we are before the collapse.

Not if we prioritise self-inquiry before crisis forces us to.

The earlier we commit to knowing ourselves — deeply, courageously — the more graceful the crossing becomes.

And those who do manage to walk that bridge — whether through collapse, curiosity, or courage —

they are the lucky ones.

Because on the other side is not perfection, but presence.

Not applause, but authenticity.

Not success as the world defines it, but self-love.

They get to live a life that is theirs.

And that, to me, is the ultimate blessing.

Understand Yourself First

This season of rupture gave birth to a conviction:

Understanding yourself must precede everything.

Before you lead.

Before you parent.

Before you love.

Before you build.

Because if you don’t know who you are — your wounds, your beliefs, your patterns, your values —

then everything you create will be built on shaky ground.

That’s why I started the Understand…First! series — a legacy of reflections I wish I had in my twenties. A toolkit for those ready to cross their own bridge.

“Your visions will become clear only when you can look into your own heart. Who looks outside, dreams; who looks inside, awakes.”

— Carl Jung

A Final Word: The Bridge Is Real, and It’s Worth Crossing

The dark night of the soul is a bridge.

A fire.

A passage.

It doesn’t announce itself.

It doesn’t ask permission.

But if you survive it — if you surrender to it — it can remake you.

So if you’re on the bridge now:

Hold steady.

Feel it all.

Let go of who you thought you had to be.

And if you’re standing on the other side:

Give thanks.

Live truthfully.

And honour the path that brought you here.

Because on this side, life isn’t easier — but it is yours.