September 24

The Best Shadow Work Questions For Beginners


My favourite time is the morning.

As I sip coffee and reflect on my life, the deepest insights come to me.

And the other day I realised something…

There’s one personal development practice that changed my life the most.

And that’s shadow work.

  • If you procrastinate.
  • If you have social anxiety.
  • If you’re stuck in a rut of bad habits.

This is your best shot at fixing it all.

Whereas most other practices focus on the symptoms.

Shadow work (an inner work practice pioneered by Swiss Psychoanalyst Carl Jung) aims to tackle the root cause of our issues.

But there’s a problem.

Getting started can be confusing as hell.

That’s why, this week I’m giving you the absolute best shadow work questions you can ask as a beginner.

Now hang onto your ass with both hands because this first question is a mind-blower.

#1 - What am I avoiding?

The cave you dare not enter holds the treasure you seek.

The first question is the most basic but it’s still something few people ever ask themselves.

Because it’s uncomfortable.

But this is a mistake.

Because when you ask yourself what you’re avoiding, you invite insights to come to you from new places.

Those insights have the power to radically shift your reality.

For example, you may be procrastinating on work because you’re avoiding having a vulnerable conversation with your boss about something bothering you.

And when you dive into this you might learn that you avoid confrontation altogether which severely limits you in life.

By exposing your avoidance patterns and reversing them, you breathe new energy and potential into your life.

#2 - What don’t I want other people to know about me?

When you’re a child you learn to play a role to get approval from people.

Role-playing is necessary and even useful if you know you’re doing it.

But when you’re playing a role without knowing it - you become inauthentic.

And the more inauthentic you are, the less of a fulfilling life you will live.

Asking this question helps you understand the parts of yourself you hide from others.

And bringing these parts into the open will help you live authentically.

#3 - What traits or characteristics do I dislike about other people?

What we dislike about other people can lead us to an understanding of ourselves.

Because what we really dislike about others is actually a reflection of the parts of us that we reject.

This is called projection.

When you can recognise your own projections instead of identifying with them.

This will improve your relationships dramatically.

#4 - Who are my role models and what traits or characteristics do I admire about them?

Your shadow isn’t all dark and destructive.

In your shadow also lies your potential for creation, light and regeneration.

They call this the golden shadow.

And it’s speaking to you right now.


Through those you admire.

There’s a reason you admire certain people.

They embody the traits and characteristics that exist in you as potential.

And this admiration is a calling from within giving you guidance on who you really are.

For example, I always respected Jordan Peterson for speaking his mind even under intense pressure. This is because I was a timid people-pleaser at the time.

I was a strong-spoken kid. Unapologetic. But I lost it along the way.

But deep down, that’s who I really am.

Now since speaking my mind more, my admiration has faded a little because it isn’t needed anymore.

So ask who you admire and why.

It gives you a road map for what you need to become in order to become your most authentic and powerful version.

With these 4 questions, you have a solid framework for building deep self-understanding. Good luck and as always...

Stay courageous.



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