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Kellie Jo Art

52 Dark Journaling Prompts: A Shadow Companion for Deep Self-Work

Cover of “52 Weeks with the Dark: Indelicate Prompts from Your Shadow” featuring a gothic window looking out onto a stark blue sky, evoking introspection, isolation, and inner reckoning.
Preview of seasonal title pages from “52 Weeks with the Dark,” a printable shadow work companion featuring 52 dark journaling prompts divided into Spring, Summer, Autumn, and Winter.
Five-page Spring section from “52 Weeks with the Dark,” featuring a seasonal introduction, 13 dark journaling prompts and commentary from the Shadow.
Redacted two-page opening letter from the Shadow in “52 Weeks with the Dark,” inviting the Seeker into a year of dark journaling prompts and emotional reckoning.
Sample Spring page from “52 Weeks with the Dark,” showing the redacted intro and one dark journaling prompt centered on fear and repetition.
Summer sample page from “52 Weeks with the Dark,” featuring a redacted page setup and showing one dark journaling prompt focused on illusions and emotional heat.
Autumn page preview from “52 Weeks with the Dark,” highlighting a single dark journaling prompt about haunting memories and spiritual connection.
Winter prompt sample from “52 Weeks with the Dark,” showing a 2 redacted prompts and redacted message from Shadow, giving one dark journal prompt about ignoring things you don't want to see.

52 dark journaling prompts crafted in the haunting voice of your Shadow. A seasonal, printable guide designed to uncover what still hurts, haunts, and holds power.

$14.99

This isn’t a gentle guide.
It won’t hold your hand.
Healing may follow—but honesty comes first.

52 Weeks with the Dark: Indelicate Prompts from Your Shadow is a downloadable, seasonally-structured journaling companion built from discomfort—not affirmation. It’s raw, poetic, and intentionally unpolished. Inside, you’ll confront the parts of yourself that polite healing work often avoids.

This is not your average collection of journal prompts. These are dark journaling prompts written in the voice of the Shadow—unapologetic, unnerving, and painfully honest. Each one opens a door to the parts of you you’ve tried to forget:

  • The memories you avoid
  • The patterns you justify
  • The truths that hurt too much to name

The Shadow doesn’t want your gratitude. It wants your attention. And it’s been waiting.

What’s Included:

  • A beautifully designed, printable PDF
  • 52 original prompts arranged by season
  • Shadow-written letters to open and close your journey
  • Four themed sections: Spring, Summer, Autumn, and Winter
  • Each prompt paired with a haunting poetic stanza
  • Font-embedded for clean printing and journaling ease
  • Undated—start any time, repeat when needed

This isn’t about healing. It’s about reckoning.

Let this be your ritual.
Your reminder that what still hurts… may still have something to teach you.

You don’t need to be ready.
You just need to begin.

Pick up the guide. Open to page one.
See what crawls out.

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