by Oli Anderson, Transformational Coach for Realness
How to Do Shadow Work Without Getting Stuck in the Shadow Territory
Shadow work is often framed as one of the most essential processes on the journey toward healing, integration, and alignment with one’s deeper purpose and realness.
This is because when it’s done in a way that’s aligned with reality, then it has the potential to help us become more whole, more real, and more capable of taking real action that reflects our true potential.
Here’s the catch, though:
Many people fall into a trap where “doing shadow work” becomes an identity in itself and so it becomes a never-ending loop of excavating pain without ever truly integrating, embodying, or moving forward and so – instead of ‘healing’ – it just leads to becoming stuck in what I’ll call the Shadow Territory.
This article is for the seekers who have lingered too long in this territory and who find themselves constantly poking and prodding old wounds without making any meaningful progress in their lives:
I want to help you understand why this happens and offer concrete, practical steps so that your shadow work truly serves you and your life instead of holding you prisoner to the unfaced aspects of yourself.
Let’s dig a little deeper:
Stuck in Shadow Work: What We’ll Cover in this Article
- How to Do Shadow Work Without Getting Stuck in the Shadow Territory
- The Reality of Shadow Work: What Shadow Work Really Is (and Is Not)
- Why People Get Stuck in Shadow Work
- How to Move Out of the Shadow Work Stuckness – 7 Practical Steps
- What It Looks Like When You’re Moving Through the Shadow Territory, Not Stuck and Living in It
- An Example (Composite, for Illustration)
- Obstacles You’ll Likely Face (And How to Meet Them) as You Become UNSTUCK
- Final Thoughts: From Shadow Work to Realness
The Reality of Shadow Work: What Shadow Work Really Is (and Is Not)
First, let’s clarify exactly what it is that we’re talking about when we say “Shadow Work”.
The truth is that Shadow Work isn’t about indulgent nostalgia or endlessly dwelling on past wounds (though it’s often sold as this in the spiritual bullsh*t communities):
Though facing and integrating the past is one component, real shadow work is about uniting past, present, and future into a coherent whole, so that what was exiled into darkness can be welcomed back into the light of conscious life.
This means that true integration at this level supports taking aligned action and moving toward your real-life purpose.
When shadow work is over-romanticised – or reduced to a kind of suffering aesthetic – it becomes possible for people to confuse stagnation for depth which is when you’ll hear people say things like, “I’m just doing my process / doing my shadow work” as though that gives you permission not to move.
The way to tell the difference between actual shadow work and this kind of stagnation is pretty simple, though:
If the result is more confusion, more rumination, and more stuckness, then you’re not actually healing (which is what real shadow work is supposed to help you do) – you’re PERFORMING it.
In the deeper sense, shadow work is about making parts whole so that you can live more fully:
It’s not about battening down broken pieces forever but about retrieving your exiled self and all of its ‘stuff’ and bringing it into integration so you can live from the newly expanded foundation of ACCEPTANCE beneath you.
Why People Get Stuck in Shadow Work
Below are the key dynamics I often see in people who become stuck in the Shadow Territory – understanding these really is the first step into shifting back into your realness if you’re dealing with this problem:
1. The misconception: Shadow = “all ‘bad’ things”
One of the most pervasive myths about the shadow is that it contains only repressed, ugly, shameful, or ‘negative’ aspects of ourselves like anger, envy, guilt, self-loathing, hatred, or brokenness.
While it’s true those energies may dwell there in the Shadow Territory, that is not all that’s there:
If you treat the shadow as a morgue of villainous parts, you’ll tend to dredge up only the painfully negative, reinforcing the very ego that sent those parts into exile in the first place (if you don’t know, the ego and the shadow are in a constant battle for dominance in our lives – check out this article about this Shadow Dance: The SHADOW DANCE: The Uncomfortable Truth About Why You’re ‘Stuck’).
This just opens up a vicious loop because it means that the more you “look into your shadow”, the more you affirm the negative, and so the more you believe yourself broken. What’s actually happening here is that you end up recycling the ego’s story instead of dismantling it so you can replace it with something more real (the ‘stuff’ in the Shadow Territory that’s waiting to resurface in your life).
What’s actually true is that the shadow also houses disowned gifts, strengths, and potentials – i.e. all of the things you have hidden because they were inconvenient, too threatening, or too unsupported in your upbringing or social context. This means that in the shadow might dwell your capacity to trust, your self-belief, your real creative gifts, your deepest values, and the seeds of your future goals.
When people only focus on digging up the pain, they never rediscover the treasure but when they begin to face and integrate the good shadow aspects, they start reclaiming the building blocks for a more grounded, embodied, real life.
2. Overfocus on past + present (through ego-filtered lens)
Another direct path into shadow work stuckness is this:
People confine shadow work only to the past and the present but in a past and present that have been filtered through ego-reinforcing narratives.
This means that the shadow work isn’t being done from a place of real presence but only ever serves as a kind of re-enactment of the same stories that come from being detached from one’s natural state of realness: “I feel worthless, I feel abandoned, I feel flawed”, etc. – all of which keep the ego on replay.
This just means that when you look into your past, you discover ‘evidence’ of your current low feeling in the present (which is really just the ‘present’ your ego is showing you – not the actual present moment).
In this state, you end up identifying with those emotions, replaying the same griefs, justifying them, and thereby reinforcing your identity as being ‘wounded’.
That is not healing, though – it’s just endlessly looping and running around in circles whilst giving the illusion of going somewhere (because you’re doing all that ‘Shadow Work’).
Thankfully, the way forward here is pretty simple:
What’s missing is a future orientation – a sense of where you want to go, who you want to become, and how you can channel what you uncover down their in the Shadow Territory in service of that direction.
The bottom line is that without this kind of horizon, shadow work remains rootless, murky, and disconnected from life and you’ll spend the rest of your life doing it without getting anywhere.
3. Romanticising pain & attachment to suffering
Another big psychological trap is to romanticise pain and to treat it as a badge of depth or as a signature of being “artistic” or “spiritual” or whatever.
Essentially, you may unconsciously hold on to your pain because it gives you a kind of identity or because you feel it makes you more ‘interesting’ or ‘significant’ in some way.
There’s can also be an unconscious attachment to the one who caused the pain:
What this means is that – in some cases – by not letting go, you maintain a connection, however painful, with people from your past which provides a kind of predictability and familiarity.
When all this is going on, even when a breakthrough wants to emerge, you resist it because letting go signals change, risk, and stepping into unknown territory (which people lost in the ego fear more than anything because their natural capacity to TRUST themselves and life is buried in the Shadow Territory somewhere).
All of this leads to you staying in the ‘comfort’ of your (now) familiar pain – even if it’s hurting you deeply.
How to Move Out of the Shadow Work Stuckness – 7 Practical Steps
Here’s a roadmap for shifting out of the stuck shadow work cycle into a process that’s more dynamic, integrative, and alive.
None of these steps are something that you do just one time and then you’re ‘done’ – instead, they form a spiral you can keep returning to and going deeper into the process of removing layers of fragmentation and becoming more whole.
Here we go:
1. Recognise and name the loop
The first step is always AWARENESS and so you first need to become aware that you’re stuck in your own shadows:
A good step is to jot down how often you cycle through revisiting the same wounds or complaints and then pay attention to naming the narratives (e.g. “I’m unlovable,” “I’ll always be broken,” or “I’m not enough” etc.).
Recognising the pattern is often half the battle because once you’ve recognised it you can start to detach and remove the power it has over you (when you just let it run on autopilot).
You might journal:
“Here’s how I tend to replay childhood abandonment in my relationships…” or “I keep thinking that I’m inadequate because of past rejection”.
Be honest and accept the core facts at this stage:
You’re stuck in a loop which means you’re not progressing or moving forward.
2. Invite curiosity, not judgment
When you turn to the shadow, bring the attitude of a gentle explorer instead of some kind of judge or prosecutor.
You don’t have to ‘prove’ to yourself (or anybody else, for that matter) how wounded you are – instead, you simply ask:
What’s been exiled? What parts of me haven’t had a voice?
Then let these parts speak.
Other useful questions might be:
“What am I hiding from? What’s afraid to be seen? What is this pain trying to tell me?”
Sometimes, when you lean into the fear, a small flicker of a resource or gift might surface.
3. Search for the ‘good‘ parts in the shadow
Like we said, this is often neglected because the common misconception is that the shadow is only the ‘bad’ stuff.
This being the case, it’s essential once you find something painful to ask yourself:
“Could there have been something beautiful or valuable related to this that’s been disowned?”
For example:
- If you found a fear of trusting others, did you also bury your capacity to trust deeply?
- If you found shame about being seen, was there a quality of bravery or authenticity you suppressed?
- If you found guilt or over-responsibility, did you bury your ability to hold responsibility or care deeply?
Begin to reconnect with these gifts and even if they feel faint right now, then attend to them by naming, them, writing them down, and speaking to them.
Start re-anchoring your identity not only in the wounded parts but in the reclaimed seeds of yourself and your realness lost to the Shadow Territory.
4. Cultivate healthy tension with the future
Begin to imagine – or to reimagine – the possibility of your real future:
This doesn’t have to be a grand, fully formed vision – instead, you can start with a seed image, a phrase, or a feeling:
What kinds of life would feel real to you? What is meaningful? What are you longing for?
From that imagined future, relate backward into your shadow work by asking how the ‘parts’ you’ve found can serve this future and carry you towards it.
If I re-integrate this gift, what could it help me build?”
This gives the shadow direction which is what it needs to become ‘unstuck’.
In short, you’re converting raw emotional material into something creatively generative and so the shadow is no longer just wounded memory but becomes fuel for growth (if given an orientation to be channelled into through real action).
5. Take small embodied steps
Shadow work can get overly cerebral and ‘think-y’ if you stay stuck in the mind, memories, or emotions.
This is why, eventually, you’ll need some kind of somatic and embodied practice.
Some examples might be:
- Movement, dance, or bodily awareness (notice where shock, tension, sadness reside in the body).
- Imagery, art, or poetry to give shape to what you cannot express in words and allow the unconscious mind to do most of the work.
- Rituals of release (write a letter you don’t send or bury something symbolically).
- Affirmations or mantras that gradually invite you toward the reclaimed parts (“I am worthy of trust,” “I am worthy of being seen”)
- Micro actions aligned with your future gaze (e.g. a small creative project, a new habit, or a step toward a longed-for direction).
These steps are your way of testing whether your shadow work is working – i.e. whether it leads into life or keeps carrying you away from it.
There are loads more Shadow Work exercises on this page: 100 Shadow Work Exercises: Making the Unconscious Conscious & Growing Real
6. Cultivate capacity for paradox
A huge cause behind staying ‘stuck’ is demanding clarity or purity too quickly:
You may want to say things to yourself like “I need to heal this completely before moving on” or “I have to be totally safe before initiating a new direction” but, actually, shadow work and growth often require living with paradox:
- You can feel pain and still move toward joy.
- You can integrate dark aspects while stepping into light.
- You can hold uncertainty as you lean into what you long for.
Let the tension between your present wounds and your future possibility be a womb for transformation instead of a barrier.
You don’t need to solve everything perfectly or completely – you just need to stay engaged with integrity and curiosity and keep moving forward (towards that vision).
7. Seek transformative support & structure
Because it’s easy to get lost, many people benefit from external support and structure:
- A coach or other type of guide familiar with shadow integration.
- Group work or community where you can share safely.
- Accountability systems (journaling, weekly check-ins, shadow practice routines).
- A curriculum or container that helps you move in strategic steps instead of just free roaming through the Shadow Territory with no direction.
This kind of structure helps prevent the drift into endless rumination and ensures that your shadow work is anchored in transformation.
What It Looks Like When You’re Moving Through the Shadow Territory, Not Stuck and Living in It
Here are a few clues that your shadow work is serving you rather than keeping you captive in your own Shadow Territory:
- You feel a gradual strengthening of self-acceptance instead of further diminishment.
- You start to use insights in your life and take real action: relationships shift, boundaries shift, and you take tangible steps toward your real dreams (not your ego’s dreams but those of your own realness).
- You begin to experience a sense of coherence – your past pain, your present truth, and your vision begin speaking to one another and feeding into the same path forwards.
- You make choices from deep responsiveness in the moment – not from reactivity or wound reflex.
- You feel a greater sense of freedom and so you’re so longer beholden to despair, guilt, shame, or past identity and even though they may visit from time-to-time, they don’t rule you.
In short, the shadow becomes resource and not something keeping you jailed within yourself.
An Example (Composite, for Illustration)
Let’s imagine “Maya” – somebody who has been doing shadow work for years but feels stagnant:
She keeps journaling about her abandonment by her father, about her anger, and about how loyalty got twisted into co-dependency.
Despite all this ‘work’, she doesn’t feel any freer and so she still self-sabotages, still doubts her gifts, and still hesitates to bring her creative ideas into the world.
Here are some things that Maya might do to shift from unreal to real:
- Recognise the loop: She notices her favourite journaling prompt leads to the same narrative: “I was never enough” and reinforces her ego ‘stuff’.
- Invite curiosity: She asks, “What if there was something else buried here instead of just pain?”
- Search for the gift: She realizes that beneath her abandonment wound lies a disowned capacity for deep loyalty, for steadfastness, and for emotional sensitivity.
- Cultivate future orientation: She allows herself to imagine a future where she uses her sensitivity as an asset – maybe to write, to counsel, or to help others feel felt so they can become free in their own relationships with themselves.
- Embodied step: She begins a small creative project – a piece of writing or a painting, let’s say – and starts to allow whatever emotion she’s feeling and direct the energy into building something real.
- Hold paradox: She lets emotions arise without needing them to fully dispatch; she doesn’t demand perfect healing before she writes.
- Structure and support: She joins a small group of other artists, shares pieces of her work, asks for feedback, and signs up for coaching to help her stay accountable as she keeps growing forward.
Over time, Maya begins to feel that her pain has not disappeared completely but she has noticed that it’s no longer the driver of her life as a whole; her gifts begin to emerge through the cracks and she starts offering them to the world in small ways that make her more real and integrated over time.
Check out my book Trust: A Manual in Becoming the Void, Building Flow, and Finding Peace if you’re ready to face your shadow once and for all and start living your real life.
Obstacles You’ll Likely Face (And How to Meet Them) as You Become UNSTUCK
- Fear of losing your identity: You may resist integration because your identity as “the wounded one” (or whatever) feels deeply familiar. Practice saying to yourself: I can hold my suffering without making it the whole of me.
- Overwhelm: Diving into shadow deepens intensity so use boundaries to protect yourself: time limits, grounding practices, breaks, and self-care rituals, etc.
- Comparisons or spiritual one-upmanship: Don’t measure your shadow work against others. You’re growing your path and they’re growing theirs.
- Perfectionism or demand for total clarity: Accept that clarity comes in increments and trust in the unfolding without thinking it will ever reach a perfect state of completion.
Final Thoughts: From Shadow Work to Realness
Shadow work needn’t be a life sentence:
The people who remain stuck are those mistaking stagnation for process, those focusing only on the negative, those filtering the present through ego stories, and those lacking a vision of what’s possible.
On the other hand, hen you reclaim both the painful and the precious from your shadow, when you bring your longing and direction into the mix, and when you take small embodied steps, you begin to transcend stuckness once and for all.
This is not about rejecting the shadow or pretending it’s gone:
It’s about welcoming it into your lived reality and uniting it with present awareness and future possibility. In doing so, you become more real, more capable, and more free to act from a place of realness.
If you’re ready to move past playing in your wounds and instead begin to build from the raw materials of your inner world, you’re in the right place.
The work is beautiful, yes, but it is meant to take you places – not keep you in the same ones.
The shadows are calling – not to trap you, but to guide you home to your realest self.
Stay real out there,
P.S. If you’re tired of being ‘stuck’ in your own shadows and not getting anywhere then book a free coaching session with me and I’ll help you start taking real action.
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