Purpose September 18, 2026

What Is the Dark Night of the Soul? Why Life Feels Worse Before a Big Change

The dark night of the soul is the hard stretch of loss, emptiness and doubt that often comes during a big life change. Here's what it looked like for me and for Paige, and what helps you get through it.

6 min read
An open journal and a coffee on a terrace by the sea

Before things get better, they sometimes have to get worse.

I came home to Malaga after six months in a camper van and three months backpacking in Southeast Asia. I had more clarity about who I was than ever before. And then reality hit. Some days I couldn't even get out of bed.

So what is the dark night of the soul? The dark night of the soul is a hard period of loss, emptiness and doubt that often comes during a big life change. Your old identity is gone, and your new life isn't built yet. Life feels worse before a big change gets better because you're grieving what you let go of, and you don't yet know how to use who you've become. It's painful, it's common, and there are ways through it.

What the dark night of the soul looked like for Paige

I first heard the phrase from Paige. She had what her own mind called "the dream job," in corporate sales. She was also working nights in Cape Town to line up with the US time zone, and she didn't realize how burned out she was.

A month before she quit, she went on a wellness retreat. "Nothing crazy. Just yoga and meditation," she told me. But in the quiet, things she had been avoiding started to come up. After a breath-work session, it felt clear. "This is not my path, I need to leave."

She thought leaving would fix it. "Sometimes when we leave, we think we're just gonna be chilling," she said. What came next, she now calls the dark night of the soul.

"Like, who am I without these titles?" she asked. "Sometimes a paycheck is distraction to not think about the next thing." Without work, she had all this space and time and didn't know what to do with it. Her grandmother was seriously ill. Her uncle had just died. Some days she slept until four in the afternoon.

"Those months were hard," she said. "I had never experienced depression before."

The Dark Night of the Soul, with Paige GoldsteinThe Art of Reinvention Podcast, Episode 1The Dark Night of the Soul, with Paige GoldsteinPaige tells her story in her own words. Watch on YouTube.

Why life feels worse before a big change

I've heard versions of this from others too. There's usually a lot of pain involved in rediscovering who you are. From what I've seen, it tends to come in three parts.

First, grief. You let go of identities you've had for years. It's like letting go of someone you have loved for a long time. That's real grief.

Second, emptiness. There's a stretch of nothing. You don't remember who you are yet, and you're still building a new sense of self.

Third, doubt. You finally know who you are, but you don't know how to use it in the world. What if I can't figure it out? What if I have to go back to the life I now know was making me unhappy?

And the bigger the change, the bigger the grief. In the book I describe four types of reinvention, and the biggest one asks the most of you.

A Full Reinvention asks you to put down status, expertise, community and income, all at the same time, which is why it so rarely feels brave while it's happening. Mostly it just feels like loss.

From The Art of Reinvention

If you're not sure how big your own change is, the Reinvention Type quiz takes ten questions and tells you which of the four types you're facing.

My own dark night after the van

When I came home, I had shed my old identities. I knew I was a Guide. I had clarified my core values: Adventure, Inspiration, Impact. I had a beautiful Ikigai.

But I came back to a life that had nothing built for that new person. Blue skies and clear beaches were replaced by a rainy Malaga winter. A relationship that didn't survive was replaced by an empty apartment. No job, no structure, no plan. An empty fridge, and a savings account that was getting dangerously low.

I tried reaching out to friends. But their lives had continued while I was away looking for myself. I felt like a ghost.

I binge-watched Netflix, and I don't even like TV. I decided I should look for a job, but I couldn't make myself open my laptop. If I did, I would just stare at the screen. For hours. I lacked inspiration. I lacked motivation. I lacked drive.

That's the warning I want to give you. Figuring out who you are doesn't automagically create a new life that fits. I was used to the halls of Google and the fast changes of a startup. I knew very little about being a Guide, or how to build a life around it. A Warrior without anything to fight. A Guide without anyone to guide.

How to get through the dark night of the soul

There's no exercise in this chapter of the book, on purpose. But Paige's story and mine point to a few things that help.

  1. Let yourself feel it. Paige said that if she had tried to push through, she wouldn't have had the realizations she did. "It's okay to not always be okay."
  2. Give yourself quiet time. Paige spent time alone, went on long walks and filled an entire journal.
  3. Talk to people who have been there. She called a few friends she trusted, people who had left similar jobs.
  4. Start the thing you've been putting off. Paige had wanted to do a yoga teacher training for ten years. She signed up for a 200-hour course and started a daily meditation practice. In one of those meditations she got the idea for her business, The Ripple Effect.
  5. Get help. Paige worked with several coaches. I didn't ask for help, and I went through my worst months alone. I don't recommend it.

A coach can help you figure out direction and build the next thing. That's what I do in my coaching. But if what you feel is closer to depression, a coach isn't the right person. If you feel hopeless for weeks, can't get through normal days, or have thoughts of hurting yourself, please talk to a doctor or a mental health professional. And if you're in danger right now, call your local emergency number. There are ways to get through it. Paige and I both did. But you might not be able to do it on your own.

How to help someone in their dark night

When we're at our lowest, that's also when it's hardest to ask for help. I have amazing friends and family who would have loved to help. Some tried. But I barely noticed.

So if you think someone you know is struggling, please give them a call. It might mean more to them than you can imagine. And don't ask them how you can help. They'll most likely say no. Instead, just do the thing you were thinking of:

The dark night of the soul in The Art of Reinvention

This post is based on "The Dark Night of the Soul," a chapter in the Rediscover part of The Art of Reinvention. I debated whether to include it at all. But I think it's important to be honest that reinvention isn't always easy. Your dark night might come at a different time, or look different. It might also teach you something you needed to learn.

The Art of Reinvention, by Ken HellemThe back cover of The Art of ReinventionHover for the back. Click for the book.Tap to see the book

If you're taking a break to reflect, read what a micro-retirement is too, and plan for the part where you come home. The full chapter, with Paige's story in her own words, is in the book. I went through my worst months on my own. You don't have to.

Questions people often ask

What is the dark night of the soul?

It's a hard period of loss, emptiness and doubt that often comes during a big life change. You have let go of an old identity, like a job title, but you haven't built the new life yet. It can feel like the change was a mistake, even when it wasn't.

Why does life feel worse before it gets better?

Because you are grieving what you let go of, like status, expertise, community and income. Then there's a stretch where you don't know who you are yet. And even when you do know, you don't yet know how to use it in the world. The bigger the change, the bigger the grief.

How long does the dark night of the soul last?

There is no fixed length. For Paige and for me it lasted months. What helped her was letting herself feel it, taking quiet time, talking to people who had been there, and getting help. I went through mine alone, and I wouldn't recommend that.

Is the dark night of the soul the same as depression?

They can overlap. Paige told me she experienced depression for the first time during hers. If you feel hopeless for weeks, can't get through normal days, or have thoughts of hurting yourself, please talk to a doctor or a mental health professional.

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