How Many Times Can You Go Through a Dark Night of the Soul? (More Than You Think)

There is a version of the Dark Night of the Soul story that goes like this: a person hits their lowest point, undergoes a profound transformation, and emerges changed forever. One passage. One crossing. Done.

I understand why that story is appealing. It is also, in my experience, not how it works.

Most people I have worked with — and most honestly, my own life — tell a different story. The Dark Night is not a single event. It is a recurring passage. It comes more than once. It comes at different depths. And each time it arrives, it is asking something of you that the previous crossing did not.

This is not a sign that something went wrong the first time. It is how transformation actually works.

Why the Dark Night Returns

Think of your life as a series of chapters. Each chapter has its own identity, its own set of beliefs, relationships, and ways of making sense of the world. When one chapter ends and another needs to begin — when the old version of you can no longer carry you forward — a Dark Night opens.

You cross it. You grow. You emerge into a new chapter.

But eventually, that chapter ends too. A new threshold appears. And the passage opens again.

The triggers change. The first Dark Night might arrive through a relationship breakdown in your twenties. The second through a career that has stopped working in your thirties. The third through a health crisis, or a loss, or the quiet devastation of a dream that hasn't materialised. Each one arrives through a different door. But the underlying dynamic is the same: something you have been is ending, and something you have not yet become is being called forward.

The Depths Are Different Each Time

Not every Dark Night is the same depth. Some are profound and disorienting — they shake the foundations of your identity and require months or years to move through. Others are shorter, narrower passages — a specific belief that needs to change, a relationship pattern that needs to end, a chapter that needs to close.

I sometimes think of it the way musicians describe mastery. You learn the same scales over and over — but each time, at a different level of refinement. What felt impossibly difficult at twenty feels accessible at forty. And what you couldn't even perceive at twenty becomes the next frontier at forty.

The Dark Night works similarly. Each crossing takes you deeper into your own authenticity, your own values, your own capacity to live without fear running the show. The passages become more refined. The growth becomes more specific. The person who emerges each time is closer to who they actually are.

What This Means If You Are In One Now

If this is not your first Dark Night — if you have been through something like this before and thought you were done — I want to offer you something more useful than reassurance.

This is not a relapse. It is not evidence that the previous crossing didn't work, or that you are somehow more broken than other people. It is evidence that you are still growing. That life is still asking something of you. That there is more of you available than the version that emerged from the last passage.

The question is not “why is this happening again?” The question is: what is this one asking?

Every Dark Night has a specific question at its centre. A specific belief that has run its course. A specific identity that can no longer serve you. A specific fear that is ready, finally, to be healed. The sooner you can orient toward that question — rather than toward the suffering itself — the more purposefully you can move through it.

You Are Not Starting Over

One of the most painful aspects of a second or third Dark Night is the feeling of going backwards. You worked so hard. You grew so much. And here you are again, in the dark, wondering if any of it meant anything.

It meant everything. You are not starting over. You are going deeper.

The person crossing this threshold is not the same person who crossed the last one. You have more tools. More self-knowledge. More capacity to hold the discomfort without being destroyed by it. Even when it does not feel that way — especially when it does not feel that way — that growth is real and it is with you.

The Dark Night returns not because you failed the last crossing. It returns because you succeeded — and because there is more of your life waiting to be lived.

If you are in one now and want to understand what it is asking of you, I would love for you to join my free webinar.

You can also read more about what the Dark Night actually is here.

Or explore signs that you may be in one here.