3 Shadow Journal Prompts to Explore The Wounded Masculine - Entitlement

I prefer the term Wounded Masculinity over Toxic Masculinity because wounds can be healed.

When we think of something as toxic, our instinct is to avoid it entirely. For men, being labeled "toxic" often leads to shame, which can make them withdraw instead of engaging in self-reflection. But if we recognise these behaviors as wounds, it opens the door to healing, accountability, and transformation. Remember, your wounds may not be your fault but your healing is your responsibility.

The Wounded Masculine’s sense of entitlement has shaped society for generations, manifesting in deeply harmful ways: human trafficking, environmental destruction, and violence against women and children.

At its root, entitlement teaches men that they are the rightful takers—of space, of resources, of people’s bodies, time, and energy—without consequence. This is further reinforced by the way girls are raised to center men in their lives, while men are raised to center themselves. If both men and women are conditioned to prioritise men, who is looking after the rest of the world?

This is not about vilifying men—it is about understanding where these wounds come from and how they can be addressed.

Some argue that entitlement stems from traditional gender roles that have positioned men as providers, creating a false sense of ownership over what they provide for. Others see it as the inevitable result of systemic patriarchy that rewards dominance and extraction.

Regardless of the perspective, the key is to shift from blame to responsibility. These journal prompts will help you examine where entitlement shows up in your life, whether you’ve experienced it, internalised it, or even unknowingly upheld it.

“Where in my life have I felt entitled to someone else’s time, energy, or emotional labour?”

Why This is a Profound Question:

Entitlement can be subtle. It’s not always about grand acts of control—it can show up in expectations, assumptions, and unspoken demands. This question helps uncover where we may have unknowingly expected something from others without considering their autonomy.

What to Notice as You Write:

• Have you ever felt frustrated when someone set a boundary with you?

• Have you assumed emotional support without reciprocating?

• Have you expected access to someone’s time, attention, or body without explicit consent?

• If so, where do you think these expectations came from?

  
  

“What messages did I receive growing up about what men ‘deserve’ and what women ‘owe’?”

Why This is a Profound Question:

From childhood, many of us are fed implicit and explicit messages about power dynamics between men and women. This prompt encourages deep reflection on how these early influences shape our adult relationships and worldview.

What to Notice as You Write:

• Were you taught that men should always be respected, no matter what?

• Were women in your life expected to be self-sacrificing or accommodating?

• Did you hear phrases like “boys will be boys” or “a good woman stands by her man”?

• How do these ingrained beliefs affect your expectations in relationships today?

“How can I unlearn entitlement and embrace mutual respect, consent, and reciprocity?”

Why This is a Profound Question:

Acknowledging entitlement isn’t enough—healing requires action. This question shifts the focus from awareness to change, encouraging self-accountability and new ways of interacting with others.

What to Notice as You Write:

• What practical steps can you take to challenge entitlement in yourself and others?

• How can you hold yourself accountable in relationships, work, and daily interactions?

• Are there habits or beliefs you need to let go of to foster true mutuality?

• What does respect and reciprocity actually look like in practice?

If these prompts resonated with you, imagine the transformation that comes with a fully guided Shadow Work journey.

✨ The Compact Shadow Journal is perfect for beginners who want a structured yet approachable way to start.

If you need to learn more before taking that deep dive, read about our blog posts on both our Compact Journal and Concise Journal to discover the wonderful ways Empowered Solitude can help you take the next step toward self-awareness and healing.

✨ The Concise Shadow Journal dives even deeper, offering more chapters and prompts for those ready to commit to self-discovery.

If you're ready to meet yourself on a deeper level, start your journey today.

Healing the wounded masculine’s sense of entitlement is not just about individual change—it is about dismantling harmful structures and rebuilding healthier ways of relating to one another.

True strength is not found in dominance or control, but in self-awareness, accountability, and the courage to unlearn.

When entitlement is replaced with mutual respect, we create space for a world where power is not about taking—it’s about sharing.

It takes all kinds to make a world!

So remember, I am entitled to my beliefs and you are under no obligation to believe me.

Use your wisdom, take what resonates and treat the parts you disagree with as a fairytale.

Thank you for reading and wherever you are in the world, I wish you a worthy day!