The Villain Challenge: The Shadow Self as Creative Catalyst
What: Think 75 Hard but for your creativity.
When: Group Prep Aug 27-30; Challenge Sept 1-30
Cost: $299 thru Aug 22 | $349 Aug 23-Sept 1. Enrollment CLOSES Sept 1, no exceptions.
Important Dates: Orientation/prep call Aug 27 7pm ET, Challenge Workshops Every Monday 7pm ET — 9/1, 9/8, 9/15, 9/22, 9/29 — replays sent for those who cannot attend live
all sales are final. no refunds, credits, transfers. full course details, reviews, etc below.
Video IntroThe Villain Challenge: The Shadow Self as Creative Catalyst
Intro to our Villain Challenge container, what to expect, what's included. etc. Please note: Sept 25 has 6 workshops, about 10hrs, updated from this video. the sept 25 offering updated on squarespace page as of August 8
How would it feel to pursue your art like a villain?
What if the missing piece of your best art belongs to your inner villain? You're not stuck because something's wrong with you. You're stuck because you refuse to touch what terrifies you most. On the road to mature artistry, avoiding critical discomfort is ambivalence, adolescence you mistake for defect.
Only a villain can do what you are afraid to do. The Villain Challenge invites you to break the rules that keep you stuck, to color outside your lines in ways you cannot currently access, to play in your own creative landscape like your inner villain does. Do what is currently "off-limits" and discover what is needed for your best art. The catch? The thing you need is likely something you are afraid to embody—it is hidden. Only a villain can see every fear you pretend is virtue.
Rooted in shadow work, mythology, and the wisdom of elder creatives, The Villain Challenge helps you embody your inner villain (the things you are afraid to be) and unleash them into your art.
For 30 days (+ 1 orientation week), I guide you through excavation, confrontation, and integration of your most critical creative block: you. You won’t believe how thrilling and liberating it is to discover what you’ve been unwilling to do for your art.
The Villain Challenge is FUN, entertaining, educational, but it is also rigorous work if you want it to be.
My Objective:
fun, education, community
Get you out of your own way
help you create work with potency and significance
Guide you through your creative coming-of-age
Give you tools that will serve you for life
introduce you to artistry as tradition, and calling, not vocation
Challenge Rules:
Villain Workout: 45 min Workout
Villain Plotting: 45 mins on the creative work
Villain Morning Pages: Journaling in the voice of your villain
Villain Lair: Maintain an impeccable Creative Space
Villain Purification: Pick a vice, abstain for the duration of the challenge.
Villain Meditation: 10 mins/day
Villain Embodiment: Find/Create a scenario in which you can show up as your villain, every day
September 2025 - What’s Included:
6 Live Villain + Creativity Workshops (w/ Vanessa) 10 total hours
NEW: Write your mature artist statement with my help.
additional group accountability + co-working Sessions, too many to count.
community group
weekly creative exercises
Daily structured, progressive journal prompts, meticulously authored by me. Founded in shadow work, all geared toward creativity.
Access to a robust artist collective
PDF Guide: Lessons, Guided Exercises, Journal Prompts, Sources, Resources
Library of Free Villain Workouts
Discounts to 1:1 services to support your work (space limited)
replays of all workshops.
Schedule and Workshop Outline
Aug 27-Aug 31 | Week 0 | The Villain Prepares - Set your Goal! Community group opens, orientation, prep, get organized, make friends!
Sept 1-Sept 6 | Week 1 | Meeting Your Villain - discover your fear, creative the lore for your inner villain that allows you to defeat your inner coward
Sept 7-Sept 14 | Week 2 | Studying Your Villain - Your inner villain exposes the patterns that keep you stuck
Sept 15-Sept 21 | Week 3 | Battling your villain - Harnessing Your Villainous Traits of Creativity - Explore how "villainous" traits can fuel creativity, break outdated creative rules.
Sept 22-Sept 28 | Week 4 | Integrating with your villain - Strategies for long-term integration of your inner villain into your creative practice
Sept 29-Sept 30 | Week 5 | Student Becomes Master. Integrating with the world. closing.
Lots of ways to participate!
LIVE with me every week + daily in the community group. Strict accountability with peers.
Watch and engage at a distance, participating in the live workshops / group occasionally
Live with me, skip the group.
totally at your own pace, workshops and themed journal prompts sent at the start of every week.
Who Should Join?
Not just for “traditional” artists - this is for anyone feeling sick of their own sh*t, blocked, or in their own way
Creators, entrepreneurs, sole-proprietors wishing to go deeper into their process
Anyone craving a robust network of creatives, craftsman, wisdom seekers, and entrepreneurs.
Women Who Run with the Wolves (you know who you are, and you crave to be given permission…)
Nerds: Mythology, Jung, Anime, Joseph Campbell, Star Wars, James Hollis, DC/Marvel, enthusiasts.
Who Should NOT Join?
Not a Substitute for Professional Help
This challenge and community cannot replace therapy, medical treatment, or spiritual guidance. Anyone needing professional support for acute issues should seek help elsewhere.No Real-Life Villains
The Villain Challenge is for goodness, creative expression, and personal growth only. It is not an excuse or encouragement to cause actual harm. Anyone with real vendettas or malicious intent is not welcome.
Reviews
“Ms. Aldrich's depth of knowledge and facility with the component parts of the creative process is nothing short of a tour-de-force. Her ability to navigate and illuminate the creative journey is remarkable.”
- Kevin Mills, industrial designer, artist, educator.
“Life-changing! For me, Vanessa's Villain Challenge was a powerful invitation to confront my shadow—the parts of myself hidden in shame—and discover the missing piece in my creative journey. With confidence, I can say that I am no longer the person I was when I began.
Though the experience is deeply personal, the community we formed tapped into a rare and powerful magic. I cried, shared my vulnerabilities, and healed alongside people I had only just met, and that’s because everyone who enters this challenge is ready to do the deep, meaningful work required for true transformation. The support within the Discord group was unmatched. We journaled, meditated, practiced yoga, co-worked, and held each other accountable as we navigated our personal growth.
Vanessa is the perfect muse and guide for this journey. Her wisdom, leadership, and grace create a safe space where real, soul-level change can truly unfold. The value of this experience goes far beyond the dollar—it’s an investment in yourself that reverberates long after it ends. Worth every penny! This challenge opened a door to my becoming, and I will forever be grateful for stepping through it.”- Chanice Boyd, marketing, copywriter, author.
“To be clear, I didn't jump into the Villain Challenge because it sounded fun - I've been waiting for this crux moment in my journey. The final death knell for a grasping version of work and existing that no longer served me. It was Vanessa's call of maturing my creativity and the beautiful paths and depths she led us on in reading groups that aligned with my own rebirthing - I was ready to let go.
This was not easy. My villain was not easy on me. What made it easier was Vanessa's guidance and my cohort's support, openness, and, above all, their energy. We put our villains forth and rode the currents of the challenge. I broke through into multiple expanses that have only been in my dreams and meditations. When I tell you I have grown up into my Energy Being and now understand the art of my spirituality - it's too much for words. You'll have to join me in the ether. My cohort has held space for me to work and grow - they see my spirit and feel my essence, and I, theirs. We continue to hold this beautiful shared space together while we focus on our new individual journeys. The cost I paid for this challenge was worth it.”
- Aisha J, engineer, reiki master
all sales final, non-refundable, or transferrable.