Intro to the Enneagram Program at Casey and Amanda’s Place

An Invitation: Discover The Enneagram

Please join up to 12 participants to attend a 6-week Enneagram discovery program, which includes:

  • A 3-day retreat
  • 3 group video calls
  • 2 coaching calls with me
  • An optional listening partnership with another participant

This program will help you understand the structure of your psyche, or “why you have certain ‘buttons’ and why some people habitually push them.” After an Enneagram program, it is not uncommon for people to say things like, “I’ve never gotten my husband until now,” or, “This whole time I thought my boss was a jerk… but now that I understand him, it’s so much easier to work with him.” 

Josh’s Enneagram class blew my mind. I want everyone I work with to know this tool. If you are a start up founder, a leader of any organization, or a human in any other context, you should know this tool. And you should learn it from Josh.

~ Dan Teran, Founder & CEO, Managed by Q

While many self awareness tools help you identify your buttons, the Enneagram’s power is that it shows you how to transcend them. Transcendence requires time and community, and the 6-week program structure provides both.

Sarah Adler, Co-Founder of Spoon University

This program will help you…

  • Feel more powerful and grounded in your body
  • Experience your essential goodness
  • Identify what drives your personality that you’re not aware of
  • Take practical steps down your unique path to inner peace
  • See the blindspots that are holding you back in your relationships, career, and personal development
  • Develop your emotional intelligence (EQ)
  • Become a better listener
  • Develop your empathy
  • Locate where you are in the spectrum of psychological health, and see how to grow
  • Identify the gifts and liabilities of your personality structure
  • Understand what motivates people different from you
  • Communicate with others more skillfully, in a way that makes for mutually satisfying relationships
  • Learn how to support others in ways that actually help
  • See the beauty in other people, even those whom you find difficult to deal with

I took this class with my wife. It saved our marriage.

~ Brian Rook, Father, Husband, Director of Information Technology (Quanta)

Josh’s way of instructing a down to earth spiritual growth class blew me away. Josh has a practical way of teaching the hard stuff in an open, safe environment, and his class helped me identify parts of my personality that have been dormant for a long time.

Rachel Neidich-Rook

The program is designed for beginner and intermediate Enneagram students, but advanced students are encouraged.

What’s the Enneagram?

It’s a diagram of personality types that’s precise enough to be a little intense. If you’re brave enough to look under the hood of your psyche… it can be world-altering.

A Community Focus

Since the Enneagram is about people, it is best to learn it with others. The group calls before the retreat help participants “settle in” with each other and form an intentional community for honest exploration.

Josh is a gentle, yet firm teacher. He fosters mutual respect and rigorous honesty, which enables deeper learning. Within our group, individuals had varying degrees of experience with introspection. Josh seamlessly brought the group together and met each member at his/her level. I highly recommend taking the Enneagram and Josh as a facilitator.

~ Carolyn Kelly, Stanford Graduate School of Business ’17

The Program Structure

Before the Retreat:

  • 2 group video calls bring the group together and set the tone for authentic sharing and listening
  • You take an Enneagram Test online and share your results with me
  • I assign reading from our textbook, The Wisdom of the Enneagram
  • You talk with me to help identify your type and unpack first insights
  • I pair you with another participant, who becomes your listening partner (optional). The two of you have weekly calls to explore the enneagram together.

The Retreat:

At the retreat, I guide you through an exploration of the Enneagram via lecture, handouts, exercises, writing, quiet reflection, and personal sharing. I also introduce art, music, poetry, pop culture, politics, and history to enrich your understanding of each type and the other aspects of the Enneagram. Participation in all exercises is voluntary.

“Class” is Friday – Sunday from 9:00am – 7:00pm.

After the Retreat:

  • 3 weeks after the retreat, we meet for a final group video call. You’ll get to share and hear how others are integrating their new awareness into their lives
  • You can schedule an individual call with me within 3 months after the program. The time is yours to open up anything you like: ask me questions, discuss next steps on your journey, etc.
Catherine Clark, Columbia Business School ’20

I have studied and applied the Enneagram for over ten years. During this time I have attended several extended, in-depth classes on understanding and applying the Enneagram. After attending Josh’s three day retreat I gained a deeper understanding in this timeframe than all my previous training combined. The material was clearly presented, the content was rich, but overwhelmingly the value of the class – and what stood apart from all my other training – was Josh’s thorough ability to clearly and concisely distill complex information into easily digestible pieces. It was remarkable. The class was extremely well structured and facilitated deep, meaningful dialogue amongst everyone.

~ Brian Rook, Father, Husband, Director of Information Technology for Quanta

The Schedule

TBD6:30 PM – 8:30 PM PSTGroup Video Call 1: “Intro & Rules of Engagement”
TBDTBDBegin Listening Partnerships (optional)
TBD6:30 PM – 8:30 PM PSTGroup Video Call 2: “First Insights”
TBDTBDIndividual Call with Josh 1: “What’s My Type?”
TBD9:00 AM – 7:00 PM PST3-day Retreat
TBD6:30 PM – 8:30 PM PSTGroup Video Call 3: “Integration” – 7:30pm-9:30pm EST Monday, 11/11
TBDTBDIndividual Call with Josh 2: “What now?”


  • Online Test: The RHETI (Riso-Hudson Enneagram Type Indicator) (~35min)
  • Textbook: The Wisdom of the Enneagram by Don Riso and Russ Hudson, from which I will ask you to read selections (~60 pages) before the class (<$20)
  • Binder with handouts (I provide at the workshop)

Workshop Size

8 – 12 participants.


To recap, by signing up, you get the following:

  • Two individual coaching calls with me ($500 value)
  • Three facilitated video calls with the group ($300 value)
  • A 3-day thorough, intimate deep-dive seminar on this life-changing tool ($1000 value)
  • A curated binder of Enneagram materials (original handouts, poetry, art, music, & quotes) ($300 value)

Total value: $2100

I am offering the class on a sliding scale from $695 – $1595. Each participant may pay any amount in that range. This fee is “all-in” and includes all individual calls, group calls, the retreat, materials, & snacks.


Group Video Calls will be held via Zoom. You’ll get a calendar invite with a link. Same for Individual calls.

The Retreat will be at Casey and Amanda’s house in LA.

The program runs with a minimum of 8 people. To reserve a spot, please email and pay a $100 refundable deposit to me via venmo, paypal, or check. When enough participants confirm, I will notify the group, and you can complete the rest of your payment.

Questions? Please reach out!

The Facilitator

I have been studying the Enneagram in depth for over 5 years in workshops with the Enneagram Institute, New York Enneagram, and the Educare Unlearning Institute. I have over 500 hours in coaching and listening training in programs through the Educare Unlearning Institute and am currently enrolled in New Ventures West’s Professional Coaching Certification Program. I also do executive coaching and holistic life coaching.

I draw inspiration from many teachers including Parker Palmer, Ken Wilber, Peter Senge, Frederic Laloux, Wendy Palmer, Byron Katie, Russ Hudson, Krista Tippet, David Whyte, Mary Oliver, and Adyashanti.

Anna Murphy, Kellogg School of Management ’20

In all honestly, I went into Josh’s retreat weekend somewhat skeptical. I’d already explored a lot of different approaches to self development and wasn’t sure what else was to be gained. And all I can say is WOW, thank god I embarked on such a life-changing weekend. It’s scary to imagine a world where I didn’t attend. Why? I’m still processing, but here are some thoughts: In general I feel like I have more awareness and compassion for myself and others. It may sound trite, but since the retreat I’ve noticed myself observing random strangers with more curiosity and compassion where previously I would have been more likely to get annoyed or pass judgment.

My interactions with colleagues have also been easier and more enjoyable. It’s been harder to get triggered. I also learned to appreciate certain things about myself that I wasn’t aware of before e.g. my connection to my body, and the value of doubling down on that versus taking it for granted. Since the weekend I’ve been working out more and generally feeling more settled and grounded in my body. 

I’ve also gained significant clarity regarding important life decisions in front of me–clarity I didn’t realize I needed ahead of the weekend. Scary to think I may have just continued down the default path unaware of the major fork looming ahead. 

Finally, I’d say that one of the best things about the weekend was going deep with the incredible group that Josh put together. A lot of the benefits come not just from individual teaching by Josh, but the way he orchestrates the group so that people share and open up to each other with such depth. That’s the magic. I feel grateful for having witnessed such beautiful and heartfelt human interactions. And excited to feel more alive, heart open, and connected to others moving forward.

~ Carter Cleveland, Artsy, Founder & Executive Chairman

Josh is an incredible teacher, and it is clear that he has spent years acquiring deep knowledge. Every teaching moment came with stories from his own life that really brought the Enneagram to life. Josh managed to create a safe space in which I felt encouraged to dive beyond the surface and reflect and share who I am and who I might want to become. I highly recommend Josh as a teacher and the Enneagram as a framework to anyone looking to explore on a deep level who they are.

~Malte Kramer, Founder of Luxury Presence and author of Play for Something

I absolutely loved my first deep dive into the Enneagram, and Josh was a fantastic facilitator. Our group had a few first timers (like myself) and others with a lot of experience with the Enneagram, and Josh handled the dynamic expertly. Josh had a way of making everybody feel safe in sharing their true thoughts and feelings, but at the same time he was able to challenge people to ensure that our sessions together were maximized. I will use what I learnt on our retreat in my daily interactions for the rest of my life, and I recommend the class to anyone looking to deepen their understanding of human behavior/interactions.

~ Michael Hobbs, Stanford Graduate School of Business ’17, Former New Zealand Professional Rugby Player
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