Intro to the Enneagram 10-Week Program (Pilot)

An Invitation: Discover The Enneagram

Dear friends. I am inviting you to join up to 12 participants to attend my pilot 10-week Enneagram discovery program.

The program centers on a 3-day retreat outside of New York City framed on either side by group meetings, coaching calls with me, and a listening partnership with another participant.

This program will help you understand 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.” 

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 10-week program structure provides both.

This program will also help you:

  • Identify what drives your personality that you might not be aware of
  • See blindspots that may be holding you back in your relationships and career
  • 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 patterns
  • Understand what motivates people different from you
  • See the beauty in other people, even those who you find difficult to deal with
  • Interact with others more effectively at home and work
  • Experience your essential goodness
  • Take practical steps down your unique path to inner peace

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

What’s the Enneagram?

The Enneagram is a personality typing system that combines psychology and spirituality for insight into yourself and others. It’s like a map of the human inner world.

A Community Focus

Since the Enneagram is about people, it is best explored with others with whom you feel comfortable asking and answering honest questions. The group work before and after the retreat will nurture meaningful connections between participants and allow everyone to settle into a sense of intentional community.

The Program Structure

Before the Retreat:

  • 2 in-person group meetings set the tone for authentic sharing and listening (out of town participants can join by conference call)
  • You will take an online Enneagram Test and share your results with me
  • I will assign reading from our textbook, The Wisdom of the Enneagram
  • 1 individual coaching call with me will help you identify your type and unpack first insights
  • I will pair you with a listening partner — another participant with whom you will co-explore your Enneagram journey on weekly 1-hr calls

The Retreat:

By the time of our retreat, participants will be well acquainted with each other and with Enneagram basics. We will dive right into a guided exploration of the Enneagram through lecture, handouts, exercises, writing, quiet reflection, and personal sharing. Participation in all exercises is voluntary.

The retreat is divided into 3 sections:

  1. Don Riso’s Levels of Development – the revolutionary framework that describes the spectrum of psychological health from psychosis to enlightenment — available to all humans
  2. The 3 Instincts – the mammalian biological drives that influence us powerfully without our conscious awareness
  3. The 9 Types – the personality types themselves

We will spend the majority of our time on the 9 types; the Levels of Development and the Instincts will provide a foundation for our type exploration. I will introduce art, music, poetry, pop culture, politics, and history to enrich our understanding of each type and the other aspects of the Enneagram.

Participants are welcome 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 (with plenty of breaks). Sunday will end at 5:00pm.

The evenings will be free, and participants can spend the time in whatever way they feel moved. There will be ingredients for simple meals available at all times. Dietary preferences and restrictions will be accommodated.

After the Retreat:

  • 4 weeks post-retreat, the group will meet a final time, and you will have an opportunity to share and hear from others about how they are integrating their new awareness into their lives
  • A final coaching call with me will help you help you discern next steps to deepen and sustain this integration

The Schedule

  • Meeting 1: “Intros & Rules of Engagement” — 7:30-9:30pm EST Sunday, March 31
  • Listening Partnerships begin (1x/week hour-long calls with another participants)
  • Coaching Call 1 with me: “What’s My Type?” (anytime pre-workshop)
  • Meeting 2: “First Insights” — 7:30-9:30pm EST Sunday, April 21
  • 3-day In-Person Retreat– Friday, May 3 – Sunday, May 5 (Fri 9:00am – 7:00pm, Sat 9:00am – 7:00pm, Sun 9:00am – 5:00pm)
  • Meeting 3: “Integration into Real Life” – 7:30pm-9:30pm EST Sunday, June 9
  • Coaching Call 2 with me: “What do I do now?” (anytime within 3 months post-workshop)


  • 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


Because this is a pilot workshop for friends, I am offering it on a sliding scale with the lower end being the cost of food, lodging, and materials. (Likely ~$500)

Sliding scale: ~$500 (exact $ TBD) – $1495. Each participant may pay any amount in that range.

Workshop Size

8 – 12 participants.


The Meetings will be held in Manhattan (location TBD), and there will a conference line for those who can’t make it in person.

The Retreat will be held in a graceful AirBnB outside of the city. The exact venue will depend on the number of participants. Once I confirm enough participants, I will book the venue and provide location and travel details.

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

Questions? Please reach out!

The Facilitator

Josh has been studying the Enneagram in depth for 5 years in workshops with the Enneagram Institute, New York Enneagram, and the Educare Unlearning Institute. He has also spent over 500 hours in listening and coaching training in programs through the Educare Unlearning Institute and is currently enrolled in New Ventures West’s Professional Coaching Certification Program. In his personal life, Josh draws inspiration from many spiritual teachers, including Byron Katie, Eckhart Tolle, Adyashanti, educator Parker Palmer, and poet Mary Oliver.


Josh’s Enneagram retreat invites you to step into the black box of others’ minds and rethink how you approach the diverse personalities in your life. Josh is the ideal guide for this journey – empathetic, charismatic, inquisitive, and charmingly self-reflective about how his own typology textures the experience. Whether you’re looking to engage in some much-needed self discovery or explore the dynamics of your most intimate and complicated relationships, I can’t recommend this retreat enough.

~ Jaclyn “Jax” Harris, Yale Law School ‘16

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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