The Enneagram Guide to Waking Up Makes the Hard Journey a Little Easier

We have a small library of books on the Enneagram, and many to recommend among them. But a recent release that we think is particularly noteworthy is The Enneagram Guide to Waking Up: Find Your Path, Face Your Shadow, Discover Your True Self. Having already written two compendiums on the Enneagram, Beatrice Chestnut collaborates with her Enneagram business partner of the CP Enneagram Academy, Uranio Paes. The result is a book that hits the exact target that only the best Enneagram books aspire to. 

The Enneagram Guide to Waking Up can be used as an entry point even for beginners. Thus, it qualifies as the vast majority of Enneagram books do, as a primer. Yet it also works as a practical guide, giving research and wisdom, as well as meditation and reflection space, to even the most advanced practitioners.

To that end, I signed up for a 21-hour course based on walking through the book as a community, type by type. It was a profound experience and demonstrates first-hand the power and efficacy of the book (as well as the CP Enneagram community). Part of the book’s appeal is the way that Chestnut and Paes have distilled their mastery.

The fundamental idea of The Enneagram Guide to Waking Up is to use the Enneagram as it was originally intended, as a system for self-understanding in order to grow. This is a lifetime’s work, but the goal is ultimately to “transform” or awaken to our “zombie-like,” autopilot habits and unconscious patterns. In a standard 5X8 format, the guide is just over 250 pages, and yet in that space, we cover all Nine types touching on what we view as critical points of self-inquiry and the areas to use for growth.

Each chapter begins with an allegorical one-page story about this type’s personality formation at an early age, followed by five “key patterns,” or what we also call definable characteristics. Then, for each type, we discuss the “passion,” or the emotional motivation – and ultimate cause of suffering – for each given type.

The next step discusses how any given type can move into their corresponding Wings in order to grow through the gentler stretches out of our personality’s patterns. This is followed by what we think is a pretty unique Enneagram contribution unto itself, and that is to face the shadow. As Carl Jung, the famous 20th-century psychologist who brought the shadow into our common vernacular once wrote: 

“There is no light without shadow and no psychic wholeness without imperfection.”

Springboarding from the shadow work, we touch on blind spots, as well as personal pain that our types suffer through and with. While Claudio Naranjo is attributed as pioneering the instincts and subtypes, with early contributions from David Daniels and Helen Palmer, Chestnut and Paes are making their own innovations in the field with their own continued learning, documenting, and emphasis on the subtypes, among other things. For each type, we get succinct but clear summaries of the subtypes, which is broadly overlooked and misunderstood in the general Enneagram literature.

Finally, we discuss the theory of making the more challenging moves out of our personality’s unconscious sleepwalking using Arrows. Arrow work as a theory is often discussed, but not always clearly, and with many contradictory and unvalidated hypotheses. We particularly love the idea that when it comes to the Arrow work, you should aim for the “high side” of the Arrows you move toward, and that you should recognize that solid work in self-observation and deliberate approaches and applications to the Wings, should come first. 

Finally, the way through the Passion (where we began) is through the Virtue, to which we aspire. The Virtue for each type (and the peculiarities of arriving there through the subtype) is also discussed. 

While any one of these methods, theories, and applications could be the content for an entire book, the focus here is understanding the touch points for growth and self-development far more than laying out theory. As they say at the beginning, this is a “good news bad news good news story.” The good news is that you can come to a deeper understanding of who you are and are not. The bad news is that it takes work and the experience is not easy and not always pleasant. The rest of the good news is that through the work there are real results to experience, and ultimately, you can wake up to yourself.

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