How to Face Your Darkest Meditation Moments – And Find Power By Letting Go
Entering the Dark Night
It’s a cold Massachusetts evening in December 2012, and I’m sitting in the meditation hall at the Insight Meditation Society.
I have diligently followed the practice instructions for the past five days.
Each meditation session has brought me deeper and deeper.
But in the last 24 hours, things have unraveled.
As I try to observe my experience, wave after wave of intense emotions crashes over me.
The feelings run deep into my gut, hitting me on a visceral level.
I can’t hold back the tears; they stream down my face like a faucet.
And yet, for all the intensity of what I feel, I am not sad.
These aren’t tears of sorrow but more like tears of relief.
Little by little, wave by wave, I am working through some of my deepest held emotions.
And with each passing wave, things feel a little bit lighter.
A few days later, by the end of the retreat, it’s as if I’ve gone through years of therapy.
I have worked through the most challenging part of the Dark Night of My Soul, and the experience has forever changed me for the better.
Today, I want to explain this phenomenon and give you the tools to navigate your own Dark Night or any other challenging meditation experience.
Understanding the Dark Night of the Soul
The term ‘Dark Night of the Soul’ originally comes from the writings of St. John of the Cross, a Catholic monk and mystic.
He described it as a profound period of spiritual reckoning, where one must confront the very essence of their relationship with God.
In the mid-2000s, Buddhist teacher Daniel Ingram repurposed this term to describe the Buddhist concept of the Dukkha Ñanas.
The term ‘Dark Night’ is particularly fitting, as in the Theravada Buddhist maps of meditative progress, this phase is recognized as one of the most arduous and transformative experiences a meditator will endure.
Navigating the Dukkha Ñanas
While actual practice is rarely as tidy as the maps suggest, the Dukkha Ñanas usually follow a phase of strong, confident practice.
When a meditator truly grasps the impermanence of their experience and learns to release their attachment to it, they’re ready to peel back another layer.
This stage is often called the ‘rolling up the mat’ phase because many feel like their progress has suddenly vanished, and the urge to quit is strong.
But, as challenging as the Dukka Nanas are, they are actually a sign of progress.
The challenges stem from your no longer avoiding the subtler, more elusive parts of your experience.
Everything you’ve suppressed or ignored now has the space to surface.
This, combined with your sharpened ability to observe, makes the intensity even more direct.
Recurring Cycles: The Depths of the Dukkha Ñanas
The Dukkha Ñanas aren’t a one-time event but a recurring phase you’ll pass through again and again.
Each cycle digs deeper, peeling back more layers and letting go of even more resistance.
In my case at IMS, the retreat’s conditions pushed me fully into this phase.
I was no longer holding anything back, and the full intensity of my Dark Night hit me head-on.
Now, over ten years later, I can confidently say that retreat was the most grueling part of my meditation journey.
But the insights I gained were worth every moment of challenge.
Because once you’ve navigated through your Dark Night, you’ll reach the phase of Equanimity.
In this phase, you meet your experience without clinging or aversion.
You gain a new confidence in meditation and find balance amidst the turbulence.
The mind becomes an unwavering witness, calm and clear.
You’ll have trained your mind to be present, to let go even in the toughest moments, and find contentment in stillness.
Eventually, you’ll move beyond this into the level of Stream Entry—but that’s a story for another time.
Essential Skills for Navigating Your Dark Night of the Soul
Your practice might not feel like a full-blown Dark Night right now, but I promise that tough moments will arise sooner or later.
This is why the wisdom of the Dukkha Ñanas is crucial at every stage.
These skills will help you navigate the rough patches with steadiness and clarity.
And mastering the ability to work through difficult experiences in meditation is key if you want to dive deeper.
Here’s how to handle those challenging moments when they come in your practice.
Focus on Sensations, Not Content
When harsh emotions arise, we often spin stories around them, adding layers of reactivity.
While these stories might seem like they help us make sense of our experiences, they’re actually distractions.
At their essence, emotions are just collections of sensations that come and go.
Whether you’re happy, sad, or angry, etc., break it down to the bare physical experience.
Where do you feel the emotion in your body?
How does its intensity shift over time?
Are you adding reactions beyond the raw feeling?
These questions help you zero in on the core sensations behind your challenging experiences.
On the level of pure sensation, emotions become more manageable.
It’s the stories and reactions that give them their power, not the feelings themselves.
The more you see this, the easier it becomes to relax and let go during tough meditation sessions.
However, an important caveat:
If you’re unable to view your emotions at this level, or if the intensity feels overwhelming, please seek help from a trained therapist.
Meditation can support your psychological well-being, but it isn’t a replacement for professional treatment.
A therapist can help you manage your emotions at a conventional level, allowing you to delve deeper into meditation safely.
Please take this advice seriously!
You Will Want to Give Up - But Don’t!
When meditation gets tough, your mind becomes a master of excuses.
It starts spinning stories, trying to convince you to quit.
(Are you seeing the pattern yet?)
Doubt, resistance, and restlessness peak when discomfort arises.
This makes sense, of course; nobody likes the unpleasant.
But here’s the key: when meditation feels challenging, it’s not an obstacle; It’s actually an opportunity.
The friction you feel points directly to something you’re resisting in your mind.
Learn to see that resistance clearly, and you’ll eventually be able to let it go.
By embracing the discomfort, you transform it into the very fuel that propels your practice forward.
Use Physical Practices to Help You Get Out of Your Head
When seated meditation gets tough, physical practices can be a lifeline.
Practices like Yin Yoga are powerful tools that support the first two points.
Observing your body anchors you in your present-moment experience.
Because the body is tangible, connecting with it directly is easier. (This is why Yin Yoga is the backbone of my Embodied Mindfulness Program.)
In this setting, you can also release the physical manifestations of emotions.
Emotional resistance always manifests in the body, but practices like Yin Yoga help you confront it head-on.
Sometimes, even a simple walk outside can loosen the grip of resistance.
So while it’s vital to commit to your seated meditation, integrating physical practices when things get challenging can be a wise move.
Accept Absolutely EVERYTHING
The Dark Night only holds power over you if you fight against it.
It’s the act of resisting that sharpens the pain, turning discomfort into suffering.
The tension of pushing back intensifies the challenge, making it feel unbearable.
When you find complete acceptance, challenges transform into opportunities.
You will still face tough times, but they’ll become just another part of the journey.
But if you try to compartmentalize or bypass the difficult stuff, you’re setting yourself up for failure.
You’ll only delay the process, allowing the unresolved issues to fester and grow.
The more you push them away, the more intense and overwhelming they’ll become when they resurface.
As Ajahn Chah said: “If you let go completely, you will find complete peace.”
Letting go is always the path to liberation.
The more you practice it, the more peace you’ll experience—even in the face of your most challenging meditation moments.
The Journey Through Darkness
While meditation can bring deep peace, it’s also a journey into your deepest challenges.
So remember, the Dark Night of the Soul isn’t a barrier; it’s a pathway to transformation.
Embrace the discomfort, and you’ll turn it into the driving force behind your growth.
The deepest power of your practice lies in your ability to accept absolutely everything.
Welcome it all—joy, pain, resistance, and release.
Each challenge invites you to look deeper and let go of your most conditioned patterns.
So when the urge to quit creeps in, remember that the real work happens during these difficult moments.
Let go completely, surrender to the experience, and you’ll discover a profound peace beyond the chaos.
Because the lessons of the Dark Night are just the beginning of something far more significant.
If you want guidance on your own journey towards awakening, please consider joining The Embodied Mindfulness Program.
Contact me, and we’ll set up a call to see if the program is right for you!
