Kelly-Ann Maddox

Shadow work is wondrous. You already know

that – you wouldn’t be reading this workbook
right now if you didn’t! But damn, it can also be
messy and scary and just plain hard work.

As you move through these slap-in-the-face,

shake-you-by-the-shoulders journal prompts, don’t
forget to celebrate the strength you are showing.
Don’t forget to remember how awesome it is
that you’re showing up in this big, bold way,
shining light into the forgotten corners and
under the bed – looking for monsters at the back
of the wardrobe. You are a warrior of the
psyche and that’s epic! You are at the very
centre of your own story – the hero around
which the narrative collides and unfurls.

You are taking charge. You are seeking out

what you could just as easily hide away from and
ignore. That is worth your recognition.
 You can steal little slices of time to get your
journal prompts done, or you can create a
schedule to complete them in a kind of self-made
rhythm. You can decide on an intense weekend
of shadow work and self-care, resulting in 25
completed prompts which can be revisited as you
move along in your shadow work journey, or you
can just complete a couple and see how you feel
afterwards. It’s up to you – there is no ‘right’
way. Lean into this work and find something
that feels effectual to you, honey.

You might want to dedicate a candle to your

shadow work journey and light it each time you
sit down for a journaling session. You might
choose to do a meditation before beginning or a
little release ritual after wrapping up each time.
You could try chanting a mantra to open and
close your journaling time, or you might want to
time each session to coincide with your favourite
moon phase. The possibilities are deliciously
endless!
Remember that you can always add more paper
if you feel that a lot of words need to come forth,
or take your scribblings onto the back of the page
you’re using– it’s up to you.

If you find that full sentences aren’t coming

easily, try writing in a more fractured, poetic
style or just jotting down key words. You can
always revisit the writing and add some sticky
notes to clarify things. If you want to use the
prompts again in the future, make another print
out. Compare the two journeys and see how
differently you answered the prompts – it’s
amazing how time changes things, especially
when it comes to perception and attitude!

Above all, remember that the time you spend

doing shadow work is a sacred gift to yourself
but also to the people in your life – everyone you
come across benefits from your sincere
dedication to your personal development.
 ‘Every new
beginning comes
from some
other
beginning’s
end.’
Seneca
1 - How judged do you tend to feel on a daily basis? Explore how
much of that perceived judgement is real and how much is
imagined.

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2 - Take a look at the best and most enjoyable aspect of your life
right now. What is your underlying fear in that area and why?

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 When doing shadow work, a big part of the
journey is recognising those sticking points and
‘hot button issues’ which seem to consistently
raise your blood pressure or make you feel
crappy. Identifying those things gives you the
power to begin working at the root of them. You
can work to understand where certain fears,
complexes or negative behaviours originally came
from. Comprehending their genesis leads you to
see why they hold so much sway in your life now
and how they keep making trouble for you!

Some of your shadow material came from your

upbringing. It came from your family dynamics,
the parenting and guidance that you received
from adults or your relationships with siblings.
Some came from key experiences which defined
your response to the world around you – an
accident, some shocking news, a death, an
experience of bullying or abuse. Just as many
seemingly small, uneventful things may have
absorbed into your psyche at a deep level and
ended up influencing your decisions or thoughts
later in life.
 Shadow working helps you to see where your
complexes got their foothold in your psyche. This
makes it easy to see the triggers which tend to
‘prod’ a particular shadow and make it act out.
Arming yourself with information about those
triggers means that you can accompany yourself
into the tough times and understand how to help
yourself cope.

As you’re working through these hard-hitting

journal prompts, see if you can recognise
anything which feels familiar to you.. Maybe
something which feels ‘old’, as though you have
encountered it before. Sometimes situations,
relationships and conversations that we come
across in our lives remind us of difficulties we
encountered in the past. For example, if you felt
belittled by something that your partner said to
you and then your shadow working leads you to
realise that it reminded of the way your parent
used to belittle you when you were growing up,
you begin to recognise a root and a pattern..
This information can then shape the work so
that it is as effective as possible.
3 - Write about the last time you tried to manipulate a situation
to your advantage and examine how you feel about that in
hindsight.

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4 - Describe a scenario in which you feel that competition could
be healthy and productive. Then describe a scenario in which
competition could be toxic and unproductive. Finally, write about
your emotional response to this exercise.

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5 - What does it feel like to have your emotions belittled or
downplayed? Be as descriptive as possible and try writing about
specific examples from your own life too.

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 ‘Our uniqueness, our
individuality, and our life
experience moulds us into
fascinating beings. I hope we
can embrace that. I pray we
may all challenge ourselves to
delve into the deepest resources
of our hearts to cultivate an
atmosphere of understanding,
acceptance, tolerance, and
compassion. We are all in this
life together.’
Linda Thompson
6 - Pinpoint something that's really frustrating/upsetting you at
the moment. Then try writing an uplifting, beautiful poem about
it!

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7 - Write about the last time you ran away from your
responsibilities. Consider why you did that and what the results
were.

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8 - How can you begin to give other people more space and
acceptance to be themselves around you?

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 Shadow work is not about finding excuses to
remain locked inside your stale old attitudes or
to keep repeating negative behaviours. On the
contrary, shadow work helps you to take
ownership of your issues and realise that you
have the power to see and do things differently.

Shadow work is not inherently about changing

yourself; but if you do shadow work, you will
change!

Just through the process of witnessing and

accepting the things that you’ve tried to ignore,
you will unleash an incredibly potent force
within yourself. You will no longer be running
from the stuff which freaks you out or turns you
off.. Instead, you’ll be shaking hands with those
aspects of yourself and getting to know more
about them so that they no longer run wild and
mess things up for you! It’s ok to have a
dynamic, complex personality full of glitches,
quirks and oddities. It’s about owning it and
working with it rather than trying to squeeze it
into an ‘acceptable’ shape.
9 - Whereabouts do you tend to expect other people to conform to
your beliefs? (And what scares you the most about allowing
people to have their own beliefs in that area?)

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10 - What does the term 'superiority complex' bring to mind for
you and why?

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 You shine in your shadow work.

When you dare to put your hands down into

that dark water and touch the bottom and feel
around for objects to pull forth and inspect, you
are showing your true might. Warriors of the
psyche find that they are called to connect to the
incredible fortitude within them. They use that
fortitude to practice a very special kind of
spiritual alchemy. They take what is unwanted,
shunned, feared and apparently worthless, and
they make that stuff into pure indispensable
gold.

Though it’s not always easy, the benefits are

luminous and damn near impossible to deny!
You can’t fix a problem if you don’t know what’s
causing it. You can’t choose a path that you
can’t yet see. You can’t address something that
you’re not even aware of. Hence shadow work.
Shadow work is the business of really inspecting
what is there. Even in seeing it, things begin to
take a different shape.. The science of the
psyche is wondrous!
‘Perhaps the
truth depends
on a walk
around the
lake.’
Wallace Stevens
11 - If you could say one thing to the person who's hurt you the
most right now, what would it be and why?

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12 - Consider yourself at your worst - at a point where all of your
most negative and disruptive traits came to the surface. Capture
that version of you in your mind. Then write a letter of love,
understanding and compassion to that version of you. (For extra
credit: Read the letter aloud to yourself the next time you feel
like you’ve turned into a bit of a monster!)

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 ‘Life will give
you whatever
experience is
most helpful for
the evolution of
your
consciousness.’
Eckhart Tolle
If you come across some strange new content in
your shadow -something which you had literally
no clue was there- you may find that some strong
emotions come forth in response to the discovery.
That’s ok. Witnessing those emotions and
holding space for them is absolutely a part of the
process. Don’t skip over that stuff – allow it to
unfold. Write about it, talk about it with
someone you trust, perform a ritual to represent
your acknowledgement of it, paint a picture to
express how you feel about it..

Know that knowing makes all the difference.

You can only work with the things you are

aware of. Shadow work is the process of
reaching down deep and pulling out what lies
hidden, so when you discover something in the
depths, you know you’re doing your work well!
But it can take time to process the intense
emotions associated with the discovery of new
content which may be jarring or overwhelming.
So, take your time. Shadow work is not a race!
Something might take weeks or months. It’s ok.
13 - What does the word 'punishment' make you think of right
now and why?

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14 - Write about the different ways in which people have
expressed their anger or resentment in front of you over the last
few months. What do you notice about their different modes of
expression for these emotions?

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15 - What's the one thing you know you need to do but keep
avoiding? Write it down. Then write a step-by-step description of
actually doing it. Include every action which would need to be
involved in order to get it done. At the end of the exercise,
explore how you feel.

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 ‘There is nothing like
returning to a place that
remains unchanged to
find the ways in which
you yourself have
altered.’

Nelson Mandela
16 - When was the last time you witnessed distinctly self-
destructive behaviour, either in yourself or in someone else?
Describe it and the emotions you had at the time.

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17 - What was the last cruel thing you wanted to say to someone
in order to make them feel bad about themselves or their actions?
Write it down and then explore your feelings about it.

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 Quite a lot of the things you have shoved into
your shadowscape were put there because they
are the kind of things which may potentially
cause others to reject or judge you. When
growing up for instance, you learned that you
needed to adapt your words, behaviours and
beliefs so that they were satisfactory in the eyes
of the family/adult carers. The shadow is
therefore connected to the instinct of survival –
it’s about retaining group membership. This can
happen at work, in social groups and in wider
society.

Acknowledging your shadowy stuff can

therefore feel intensely risky. There are often
setbacks in one’s shadow work and this is because
it’s scary as hell to finally own something about
yourself which seems as though it might get you
into trouble. The truth is that owning the stuff
you try to suppress means that it’s way less likely
to get out of control and cause you to do things
which you feel as though you are powerless to
stop.
For example, if you constantly try to suppress or
deny your anger because you see it as an
undesirable thing which might alienate you from
others, your anger does not simply dissolve into a
shower of fairy dust! On the contrary, the anger
just goes underground. It starts causing trouble
in all kinds of ways which you struggle to control
and consistently fail to understand. It might
materialise as passive aggression, bullying,
violent rages, drunken fights or nasty
judgements. It might cause you to isolate
yourself from others or try to sabotage other
people’s happiness. All kinds of weird things
start happening when you don’t acknowledge
those ‘undesirable’ parts of yourself and give
them some form of expression.

As you go through the prompts, be honest with

yourself about which traits, tendencies or
emotions are perceived as undesirable by your
conscious mind and are therefore denied or
suppressed. It’s those things which could be
making the most trouble for you! It’s time to get
them out in the light be honest about them.
18 - Whereabouts do you currently feel isolated and how are you
dealing with that emotion?

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19 - Write about the biggest experience of loss for you so far this
year.

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20 - What do you currently envy in someone else's life and why?
(For extra credit: What kinds of emotions come up when you
imagine yourself having access to the thing you envy?)

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‘You might say
that we use
ourselves to
discover
ourselves.’
Judith Hanson Lasater
21 – On the first line, write out the words, ‘Insecurity is my
teacher.' Then fill the rest of the page up with your responses to
this sentence - whatever comes to mind, honey!

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22 - What does it feel like to be completely discouraged by
someone's words? Be descriptive and consider writing about
personal experiences of this in your own life.

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23 - Why is it sometimes difficult to tell the difference between
someone saying something intentionally mean and someone just
saying something accidentally thoughtless?

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‘The thing that is really
hard, and really
amazing, is giving up on
becoming perfect and
beginning the work of
becoming yourself.’
Anna Quindlen
24 - What does the term 'constructive criticism' make you think
of and why?

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25 - Which emotion do you tend to deal with in
unhelpful/destructive ways? Write about the way you usually
deal with this troublesome emotion. Then write about what your
life might be like if you dealt with it differently.

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‘I may not have
gone where I
intended to go,
but I think I
have ended up
where I
intended to be.’
Douglas Adams
 kelly-annmaddox.com
mail@kelly-annmaddox.com