Interview with an Enneagram Life Coach
Having spent a few years studying the enneagram and working with it in my own life, I often wondered what having a mentor, coach, or partner to journey with me in an established framework would be like. Would it help me to face the ugly - or dark - parts of myself with more courage? Would it provide the motivation to keep going, even in the hard times? Would I respond from the responcibility of facing up to someone about my direction?
These questions lingered until recently when I decided I’d like to ask an Enneagram coach first-hand a few questions about the process. Olivia and Douglas Rosestone of Relationship Renaissance were kind enough to take the time to answer these questions. I’d like to extend my most sincere gratitude of their time and energy.
What follows is the most thorough examination of Enneagram Life Coaching that I know of anywhere. My hope is that you’ll actively read this and engage in some conversation about it at the bottom of this page. I love to hear about agreement or dissenting views.
Without further ado…
Interview with an Enneagram Life Coach
1. First, please introduce yourself, your professional title, and your
enneagram type.
We are Douglas Rosestone (One), and Olivia Rosestone (Four), Enneagram Life Coaches.
2. In your practice, do you find that there is a most common enneagram
type that comes to you for coaching? Is there a least common type? Do
you have any inference as to why this may be so?
Over the years we have typed 100’s of people, and worked with both individuals and couples. In our experience, a person’s willingness to reflect upon their Enneagram issues has more to do with how much pain he/she is in, and not what particular number he/she may be. All types can chose to reflect, and all types can choose not to. Every type has a way of avoiding self-reflection, and every type is capable of considerable self-reflection. In this regard, a person’s Enneagram pattern is not so much the issue, as how motivated he/she is to face and take responsibility for his/her part in the suffering that he/she is experiencing. Usually, he/she has to be going through some kind of crisis, however big or small. People of every type experience difficulty in both their personal and professional lives. People of every type can successfully use the Enneagram to resolve difficult life issues, if they are willing to delve deeply into themselves, with self-honesty and compassion.
3. Do you believe that one’s enneagram type is from their nature (set
at birth) or from their nurturing (formed during early years)? Is it
possible to change types during the course of your life? Can you change
wings?
In his edifying book, The Soul’s Code, James Hillman reveals what he considers to be truly innate about the form and unfolding of our individual selves. In chapter six, Neither Nature nor Nurture – Something Else, he points out the fallacy of polarized Western thinking that assumes our behavior can only be the result of either genetic inheritance or environmental influences. Although both play an important role in our psychological development, there is according to Hillman, much more to this story. To prove his point, he cites emerging data that supports the theory that identical twins are not actually that identical. Although they share a deep affinity for each other, twins often develop psychologically into distinctly different personalities. According to Hillman, there is obviously “something else” that determines this distinction. In our work, we have identified the relational styles of identical twins and found each set of twins to be comprised of two different styles. This clearly corroborates James Hillman’s theory that “something else” is at work within the formation and expression of the human psyche. Our experience in typing identical twins has proven to us that these nine relational styles are neither the product of nature, nor nurture, but “something else,” which is best identified as archetypal or “prior” to our genetic make-up or environmental conditioning.
4. Have you ever had to stop working with a client because they “hit
their wall” or encounter so much mental or emotion resistance within
themselves that they can’t go on? Do people sometimes shut down when
you approach the end of their comfort zone?
Sometimes, and then we let them go because we only can work with people who are truly committed to facing and knowing themselves. We meet people all the time, who upon realizing that they have a readily observable pattern within them called their Enneagram style, “hit the wall”. The Enneagram is both intimate and confrontational. For this reason, when we take on clients, we ask them to commit themselves to a minimum of four months work, preferably six. During this time, we present them with a way to “recognize,” then “own,” and then “practice” with their particular pattern in order to achieve their desired goals. Most people don’t have that much trouble recognizing their pattern, because we have an easy way of showing them how they operate. In this regard, Enneagram information runs a kind of psycho/spiritual gamut from “parlor game” to “spiritual practice.” At the low-end, people just want to know something about themselves because it is fun and interesting, and at the high end, they want to be able to use what they learn in order change themselves for the better. In the beginning, most people are quite interested to learn about themselves, and we are very “non-invasive” about how we present the information. However, once we begin the “owning” part of the work, they often get resistive. Then, we are asking that they get real about where they are at, and what they are up to. If we can get people through this phase, the “practicing” stage becomes a real possibility. People see that their negative reactions have consequences. If they want to lead happier, more fulfilling lives, they need to take greater responsibility for themselves.
5. What are some techniques you use to work with a difficult client?
Do you have any methods you use to help people see themselves more
clearly or open up when the defenses go up?
A good life coach can usually figure out how to “set the client up” to look into the mirror at the parts of him/herself that are dark or difficult to see. However, this does not mean that the client will always be willing or able to accept the reflection, and then do what is required. Many times when we block the escapes of a client, we find ourselves wondering whether or not he or she will actually go there and face what needs to be faced. In this regard, life coaching with the Enneagram is part psycho/spiritual drama, and part soap opera. The main techniques that we consistently use in various ways are to:
1) always begin by emphasizing the high side of a person’s Enneagram pattern; that the client already has within him/her what it takes to deal with a particular issue.
2) ask him/her to honestly acknowledge the problem he/she is having, which includes and how and why he/she is reacting.
3) ask him/her to admit whether or not his/her reaction is “working” for him/her; in other words own the consequences.
4) show him/her from an Ennegramatic perspective according to his/her particular pattern how to stop being reactive and start being proactive.
So, you support them to acknowledge the high or light side about themselves first, in order to help them face and deal with the low or dark side later.
6. In Enneagram language, how does therapy or coaching further you down
your path? IE: Does it help move you on the path of integration, does
it loosen your enneagram fixation, etc.
Wow, we could write pages to answer this question! In a nutshell, we are completely different people, not only as a result of working on ourselves with the Enneagram, but also working with other people. Douglas, the One, has learned how to let go of his tendency to be judgmental and controlling, and be more just, serene and accepting of himself and others. Olivia, the Four has learned how to let go her tendency to be and overly sensitive and disenchanted, and be more self-affirming, inspired and realistic.
This being said, we are at odds with mainstream Enneagram thinking that refers to these nine archetypal character styles as “fixations.” This is more than a semantic disagreement. Rather than looking at the Enneagram as a psychological system that describes nine fixations, we view this amazing body of wisdom as an archetypal discovery that describes the workings of human character in all of its variations. Archetypes are composed of light, dark, and gray, as are each of the nine Enneagram styles. Referring to as them “fixations” reduces them to the low end of the spectrum, and implies that our psychological knots are real, and that there is little or nothing that we can do to transform them because they exist as persistent illusions within ourselves. We are already fallen, sinful or “bad.” Referring to them as archetypes reveals that we already have a prior or enlightened Self that is transcendent, without sin, and inherently good, and that all we must do to realize this prior Self is to assume responsibility for our lower self, or the self-defeating side of our Enneagram pattern. Although we agree with the basic Enneagram information that is out there, we take a very different approach when we work with our clients. For example, obsessive-compulsive disorder is frequently associated with the One archetype. If you tell a One that he/she has such tendencies, the label often becomes more of an obstacle than a path to personal growth. While labeling the down side of One behavior may be accurate from a clinical perspective, such labels prevent a person from being able to transcend his/her behavior, because in labeling, we make the behavior, “real.” More often than not, the person feels “put in a box” or stereotyped for having certain traits, qualities and other tendencies. So, the best thing is to acknowledge the high side or what is true within the person, and then get to work helping him/her to face the low side of his/her archetype. Otherwise, you end up pathologising the person, which unfortunately has been already built into the Judeo-Christian way of viewing human nature. In the East, human nature, while being in need of integration and healing, is viewed as inherently good or whole.
7. In closing, can you offer any advice to someone studying the
enneagram for personal development and spiritual deepening who practice
by themselves?
Before you begin to use the Enneagram in order to work on yourself, you must understand that the Enneagram is not a “psychology” system, but an “archetypal” discovery about human nature in general, and human character in particular. You may not be able to “fix” your psychology, but you can definitely work on your character! If you learn to reflect upon the Enneagram as an archetypal system, you won’t get into the trap of “stereotyping” who you are, which will put you in a box. Rather, you will be able to get out the box that you are already in, which is the low or self-defeating side of your character, and hold on to the self-fulfilling or high side. Knowing exactly what you want to get out of your Enneagram work is essential. The Enneagram is the premiere tool for self-knowledge, which can lead to Gnosis, or the ability to commune with the Divine reality as it manifests in your life. This higher level of practice cannot occur without a deep commitment to the Truth. What this means for the average practitioner is that the Enneagram both strengthens our sense of self, and reduces our ego. So, there is both a boon and an implied threat to our self-concept as we go deeper within ourselves, and examine the shadow elements, while at the same time affirming the Light. To truly confront our shadows requires tremendous self-honesty, courage and compassion. If what you want is simply to adjust more successfully to the status quo, the Enneagram can be of some help. But, if what you want is to discover what is truly within you, the Enneagram becomes a Godsend. In the words of Jesus in the Gospel of Thomas, “If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you.” In our way of thinking, bringing forth the high side of your archetypal nature will “save” you, and maintaining the low side will undoubtedly destroy you.
Thanks for coming by. Make sure to check out Douglas and Olivia’s website and to make any comments, suggestions, or just a “hello” in the comments section below!

