Intro to the Enneagram Program (Retreat 12/13-15; first call 11/12)

An Invitation: Discover The Enneagram

Please join up to 12 participants for a 6-week Enneagram discovery program that includes:

  • A 3-day retreat
  • 3 group video calls spaced over 6 weeks
  • 2 coaching calls with me
  • An optional listening partnership with another participant

This program will help you understand why people do what they do and why they have certain “buttons.” 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:

  • Identify what drives your personality that you’re not aware of
  • See the blindspots that are holding you back in your relationships, career, and personal development
  • Develop your emotional intelligence (EQ)
  • Become a better listener
  • Become more empathetic
  • 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
  • Feel more powerful and grounded in your body
  • Experience your essential goodness
  • Take practical steps down your unique path to inner peace

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 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:

By the time of our retreat, you will be acquainted with the other participants and with Enneagram basics, so we will dive right into a guided exploration of the Enneagram through lecture, handouts, exercises, writing, quiet reflection, and personal sharing. I also introduce art, music, poetry, pop culture, politics, and history to enrich our understanding of each type and the other aspects of the Enneagram. Participation in all exercises is voluntary.

You can to arrive to the retreat location anytime between Thursday 7:00pm and Friday morning before 9:00am. “Class” will be Friday – Sunday from 9:00am – 7:00pm.

The evenings are free. You can spend the time however you want. Usually, we hang out, take alone time, or go into town. There will be ingredients for simple meals available at all times. Dietary preferences and restrictions will be accommodated.

A Note on Lodging

One of the most valuable parts of the retreat is the fact that it’s basically a sleep over party. Of course, that sounds fun for some folks and nightmarish for others. There is a reason I do it.

Many retreats invite us to be in solitude. But not many retreats invite us to live communally in the spirit of self-observation.

Our personalities are always “on.” If we are open and ready, we can receive some of our most powerful insights when we observe ourselves interact with the group outside of class.

Of course, you can take as much space and solitude as you need, when you need it. All outside of class time is self-regulated, and there is no pressure at any time to interact with anyone or anything. The point is that we are co-creating a container for self-reflection, which is reinforced by temporary, respectful, communal living.

If you identify as an introvert, don’t like groups, or think that living in this communal way for a weekend might overwhelm you — I invite you simply to notice that, breathe, and determine whether it’s truly preventative for you or if you might gain something valuable by leaning out of your comfort zone.

After the Retreat:

  • 3 weeks after the retreat, we meet for a final group video call. You’ll get to share and hear from others how they 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

  • Group Video Call 1: “Intros & Rules of Engagement” — 7:30-9:30pm EST Tuesday, 11/12
  • Optional Listening Partnerships begin (1x/week hour-long calls with another participants)
  • Individual Call 1: “What’s My Type?” (with me, anytime pre-workshop)
  • Group Video Call 2: “First Insights” — 7:30-9:30pm EST Monday, 11/25
  • 3-day In-Person Retreat– Friday, 12/13 – Sunday, 12/15 (9:00am – 7:00pm every day)
  • Group Video Call 3: “Integration” – 7:30pm-9:30pm EST Monday, 12/23
  • Individual Call 2: “What do I do now?” (with me, anytime before 3/15/2020)


  • Online Test: The RHETI (Riso-Hudson Enneagram Type Indicator) ($12, ~30min)
  • 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 which I will 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 incredible, life-changing tool ($1000 value)
  • A curated binder of Enneagram materials (original handouts, poetry, art, music, & quotes) ($300 value)
  • Lodging in a comfortable AirBnB for up to 4 nights (Thursday – Sunday nights) ($400 value)
  • Breakfast, Lunch, Dinner, and snacks for the entire event (all dietary restrictions accommodated) ($150 value)

Total value: $2650.

I am offering the class on a sliding scale from $895 – $1795. This fee is “all-in” and includes all individual calls, group calls, the retreat, materials, food, and lodging.

Each participant may pay any amount in that range. Scholarships may be available and are evaluated on a request basis.


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

The Retreat will be in an AirBnB close to NYC. The exact venue will depend on the number of participants. Once enough participants confirm, I will book the venue and provide location and travel details.

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’ve spent 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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