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For Understanding Yourself, Your Patterns, and Your Relationships

Gain powerful insight into your patterns, emotions, relationships, and inner wiring through Jennifer’s in-depth trainings featuring special guest experts.

Each masterclass is designed to deliver practical clarity, meaningful self-awareness, and real-world application.
Choose the topic that speaks to where you are right now.

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Enneagram Masterclasses

with the Enneagram

Our Enneagram Masterclasses offer deep insight into the Enneagram, emotional patterns, and personal growth, taught in a way that’s practical, clear, and immediately applicable.

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These masterclasses are not surface-level lessons or generic personal development advice.

Understand the hidden patterns behind tension, miscommunication, and relational friction while navigating interactions with greater clarity and ease.

with Special Guest Roz Harris

EVERYDAY RELATIONSHIPS

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$27

Immediate Access  • Watch Anytime

Explore the deeper causes of disconnection in your closest relationships and uncover the patterns shaping how you relate to those you love most.

with Special Guest David Bell

WAY OF CONNECTION

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$27

Immediate Access  • Watch Anytime

Powerful coping strategies, plus expert-led healing exercises to guide you through emotional pain, allowing you to rebuild your life with strength and resilience. 

with Special Guest Jenni Engel

GRIEF & LOSS

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$27

Immediate Access  • Watch Anytime

Examine the patterns that fuel self-doubt and insecurity while developing a more grounded, authentic sense of confidence and personal style.

with Special Guest Angie Q

DAILY CONFIDENCE

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$27

Immediate Access  • Watch Anytime

A deep dive into the 27 Enneagram subtypes, revealing how instinctual patterns and stacking influence behavior, reactions, and growth.

with Jennifer Stanley

ENNEAGRAM INSTINCTS & SUBTYPES

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$27

Immediate Access  • Watch Anytime

Meet jennifer stanley, enneagram expert and life coach

Jennifer Stanley is known for her depth, clarity, and ability to make complex psychological and Enneagram concepts feel surprisingly practical and relatable.

Her teaching blends insight, lived experience, and real-world application — helping students better understand their patterns, relationships, and personal growth.

Through her masterclasses, Jennifer creates the kind of “lightbulb moments” that don’t just inform, but genuinely shift how you see yourself.

The voice behind the Enneagram Masterclasses

lisa ashton - commonway church

Jennifer has a creative and interactive teaching style that makes learning fun!

More importantly, she values people and has a gift in helping them move forward.

I loved watching the class experience “aha moments” as she made the material come alive. Her enneagram workshop was not only insightful but inspiring. I highly recommend.

KRISTIN PRUIS, ENNEAGRAM STUDENT

JENNIFER'S GRACEFUL STYLE AND POSITIVE PERSONALITY IS SO REfreSHING.

I have loved learning from Jen and seeing how she is able to easily translate our personal experiences and struggles into actionable advice that we can start applying immediately to our daily lives.

Jennifer is passionate about her students and always shows up 110% for anything that she does.

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frequently asked questions

You've got questions and I want to make sure they get answered. Here's what a lot of people ask me.

+  Who are these masterclasses for?

The Enneagram Masterclasses are perfect for anyone looking to enhance their self-awareness, improve their relationships, and achieve personal growth. Whether you’re fresh from our Enneagram 101 course or have other outside experience with the Enneagram, our content is designed to meet you where you are and help you grow.

+ How do I access the content?

You can instantly watch any masterclass and get access to the accompanying resource guide. You’ll have everything you need to learn how to apply the Enneagram to all of our topics like relationships, parenting, marriage, trauma, health, etc.

+ How much time do I need to watch the masterclass?

Each masterclass is roughly 1 hour long, but you can easily break it up and watch it in shorter sittings if needed.

+ How do I enroll? 

Getting started is easy! Just choose a classes and then click the enroll button to checkout and access the content instantly. Begin your journey to a more self-aware, connected, and fulfilling life today.

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Not Sure Where to Start?

Different seasons bring different questions and challenges. If you’re wondering where to begin, start with what feels most relevant right now:

choose my masterclass

Feeling tension or frustration in everyday interactions?
→ Everyday Relationships

Want deeper connection in your closest relationships?
→ Way of Connection

Navigating grief, loss, or emotional pain?
→ Grief & Loss

Struggling with self-trust or confidence?
→ Daily Confidence

Curious about your Enneagram wiring and behavioral patterns?
→ Enneagram Instincts & Subtypes