The Complete Enneagram: 27 Paths to Greater Self-Knowledge

by Beatrice Chestnut

Observe the different ways you make boundaries with people. Notice how this happens and if you register any feelings that motivate you when you’re establishing boundaries.

Observe the way you try to control situations and what your thinking is behind your efforts to establish control.

Notice when you distance yourself from others and how you do it. Are there some people you want more distance from than others? What ideas an...

Observe any fears that arise—or thoughts about how to avoid feeling fear—when you think about interacting with specif...

Unlike other Enneagram types, who may actively suffer as a result of their habitual patterns, many Fives feel relatively comfortable with their defensive posture because it allows them to feel safe and in control. It provides them with a way to get away from difficult feelings—both their own and other people’s—and it helps them avoid having to feel fear. But the Five personality is a contracted stance that actively reduces Fives’ connection to themselves and others, and thus constrains their ability to grow.

For all of us, the personality operates to protect us from painful emotions, including what Karen Horney calls our “basic anxiety”—a preoccupation with the emotional stress of not getting basic needs fulfilled.

To know all that they can become, Fives must open themselves up to the fear, sadness, and anger they may not know they have inside.

Through reflecting on how and why the Five patterns operate in the present as a protection in everyday life, Fives can increase their awareness of how they maintain boundaries and avoid engaging with the emotional part of life as a way of staying safe and undisturbed.

Questioning the reasons they habitually protect themselves from a deeper engagement with life can help Fives to develop more self-knowledge about how they hold themselves back in ways that may not serve them.

Rationalizing the desirability of the Five fixation can be part of the fixation, and it will be important for Fives to at least be honest with themselves about that, so they can make the conscious choice about whether they want to change or not.

If you are a Five, the comfort associated with resignation may be distracting you from seeing how much better life might be if you allowed for greater contact with the right people.

If you are a Five, how good might your life be if you were able to take the risk to open up more and challenge the rigidity of your defenses?

While the Five coping strategy of employing “distance machinery” through “availing [yourself] of a good wall”33 can lead to a comfortable sense of isolation, it may also intensify an ongoing fear of violation or intrusion.

What Naranjo calls “the vulnerability and impotence involved in an exaggeratedly passive and unexpressive or unfeeling disposition”34 can leave Fives feeling powerless and insecure.

Fully exploring how their defensive patterns operate can open the door for Fives to reconnect with themselves on a deeper level, and it can lead them out of the trap of having to ...

For all of us who seek to wake up, the next step in working with type-based knowledge of the personality is to begin to inject more conscious effort into everything we do—to begin to actively think, feel, and act with more choice and awareness.

Fives benefit from challenging the false belief that they don’t have enough resources to survive. Recognize that it only seems like you have limited time, space, and energy because of early pivotal and painful experiences. In reality, you have as many abundant resources as you believe you have (or let yourself have). And connecting more with other people actually increases the resources you have available to you because it expands your sources of support.

Reminding yourself to have faith in abundance initiates a positive cycle of access to more and more of what you (falsely) think you don’t have very much of.

When you view the world through a lens that sees everything in terms of the scarce resources that you have to hold on to, you may magnify your experience of scarcity. Focusing on what you have to grasp onto in order to survive only perpetuates the belief in and the reality of insufficiency.

Turn up the volume on any desires you might have to experience more of life, and support yourself in taking the risk to find ways of experiencing the world that feed you and enhance your life.

An important first step in being able to connect more with your feelings and empathize more with others is noticing when you detach from your emotions or otherwise stop yourself from feeling.

Recognize when you may be thinking about feelings rather than actually experiencing emotions. It may be important to think about feelings in the early stages of your self-work, but remember to discern the difference.

Notice when you detect an absence of feeling when you might (logically) be inspired to feel something, and allow yourself to shift your attention to your body, with the intention of being o...

For Fives who feel a longing to connect more fully with others despite their defensive personality tendencies, growth entails making continual efforts to reattach to life—making it a practice to try to engage with and express feelings more regularly.

Start by trying to feel your emotions when you are alone and then expand your efforts to paying attention to your feelings when you are with others. And try to talk more about your feelings with people you trust.

Fives are so good at doing what they do that they can go to sleep to the fact that they may be severely limited by their personality’s fixation. It can seem to Fives who live safely behind carefully constructed barriers that there’s nothing to fix.

When in the grip of their personality, Fives typically feel a comforting sense of control. They are good at avoiding people who are needy and overemotional; they excel at maintaining boundaries; and they know how to control life so they can avoid feeling their fear.

Fives specialize in avoiding situations in which they will feel fear.

Fives who seek to grow must move forward into life more, find a deeper energy source inside, and reconnect with feelings, instead of hiding deep inside themselves. If you are a Five, when the automatic defensive impulse to distance yourself arises, as a first step, experiment with just staying still and not automatically disconnecting. Start to notice how and when you withdraw and, practice staying put instead.

Whether in relationships, in conflict situations, or in your work life, play with the possibility of making the choice to move toward people and more into the flow of life. Remind yourself that learning to risk trusting the outside world is a big and wonderful step for you to take toward your own enlivenment.

The direction from the core point along the arrow line is the path of development. The “stress–growth” point ahead represents specific challenges perfectly suited to expanding the narrow focus of our core point personality.

The direction against the arrow from the core point to the “child–heart“ point indicates issues and themes from childhood that must be consciously acknowledged and owned so that we can move forward and not be held back by unfinished business from the past. This “child–heart” point represents qualities of security we unconsciously repressed, occasionally fall back into as a comfort in times of stress, and now must reintegrate consciously.

The Inner Flow growth path for Type Fives brings them into direct contact with the challenges embodied in Type Seven: using levity, sincere intellectual interest, innovative thinking, and creative options as a way of interacting more directly with the outside world.

While Fives can move to the Seven Point in times of stress, causing them to act out their nervousness in social situations through anxious laughter or a manic way of talking, they can work to ease this tension with awareness by consciously embodying aspects of the high side of Seven.

Fives can expand their ability to share more of themselves with others by intentionally using humor, playfulness, and intellectual curiosity to help them to manage any anxiety they might feel when opening up more socially.

The Five working consciously in this way can make ready use of the tools healthy Type Sevens use: creative thinking and an interest in people in support of an engaged...

The path of growth for Type Fives calls for them to reclaim their ability to engage more actively, more fearlessly, and more powerfully in the world.

The Eight Point can be a place of comfort for Fives who allow themselves more freedom to assert themselves and enforce the boundaries they need. The Eight archetype may also represent what didn’t work for Fives in their early environment.

Fives’ early impulses to act in direct ways to get what they needed—the Eight-ish strategy of self-assertion—may not have been seen or supported in childhood, and th...

However, the Eight experience likely continued to be a place Fives moved to after childhood to find comfort in feeling free to act in powerful ways to protect t...

Moving back to Eight with awareness can thus be a way for Fives to re-engage with their lost sense of their power and authority, a way for them to feel more strength in dealing with fear, engaging with their emotions, and interacting with others.

Fives can support themselves in their self-work and expansion by consciously calling on the gifts Eights have in expressing anger in productive ways, making big things happen, and asserting themselves to impact people in positive ways.

By reincorporating Type Eight attributes, Fives can consciously remind themselves that it’s okay to own your authority, express yourself more powerfully, and use strength to both make boundaries and open up to the vulnerability entailed in sharing yourself more with other people.

The developmental path from Vice to Virtue is one of the central contributions of the Enneagram map in highlighting a usable “vertical” path of growth to a higher state of awareness for each type.

In the case of Type Five, the Vice (or passion) of the type is avarice and its opposite, the Virtue, is nonattachment.

The theory of growth communicated by this “Vice to Virtue conversion” is that the more we can be aware of how our passion functions and consciously work toward the embodiment of our higher Virtue, the more we can free ourselves from the unconscious habits and fixated patt...

Nonattachment is a way of being that is oriented toward letting go of the need to grasp what feels necessary to staying safe, and opening up to a deeper experience of the natural flow of life.

Nonattachment requires Fives to explore the ways in which they hold on to and hoard time, space, and energy, and to challenge their beliefs in scarcity.

Working toward embodying nonattachment means recognizing what it means to be attached, seeing what you are attached to, and having the faith to let go of what your acorn-self personality thinks you need to hold on to to survive.

When they can wake up to the ways they cling to their ideas and assumptions about what they need to control to stay safe and supplied, Fives open the door to a deeper acceptance of life as it is. When they can do this, they can release the need for control and withholding and open up to a more enlivening engagement with the world.