Many Five children grew up in a family where personal boundaries barely existed or where one or both caregivers consistently overstepped the child's physical, emotional, or psychic boundaries. Their mother, or primary caregiver, may have been possessive, controlling, or smothering. As quiet, private souls, Five children experienced this behavior as an intrusion and guarded themselves against it by retreating into the safe, private world of their imagination.

Other Five children felt abandoned by both parental figures, or failed to bond with their mother and learned to cope with their despair by detaching from or compartmentalizing their feelings. Sandra Maitri, author of The Spiritual Dimension of the Enneagram, described a Five's memory of the early relationships as “tinged with the sense of not being fully related to, deeply loved, wanted, or fully nourished…a sense of having futilely sucked at a dry tit.”

Five children adapted to feeling rejected or to feeling smothered by skirting intimacy, by hiding themselves from the sight of others and observing others from safe distances. Five children became calm, cool observers who retreated from life and felt safer dealing with mental concepts than messy feelings. If they experienced their mother — or mother figure — as devouring, they probably developed a belief that intimacy was draining and that they were better off conserving their energy than feeding into someone else's emotions. Suffering from early disappointment, Five children lose their faith in hope, preferring predictability to surprise.

Five children learned to retreat to their own rooms or to a compartmentalized psychic space that permitted them time to mull over their emotional reaction. They learned to like their time alone and often resorted to hiding even when in public. Eventually, they became observers of life more than fully engaged participants and often would not know what they felt about an interaction until they had time to think about it later.

Five children needed order and strongly preferred to know ahead of time what was on their agenda. They developed an affinity for mental preoccupations and would rather fade into the background than be singled out or put on the spot. They would often feel drained when around others and resisted authority at every turn. They spent a lot of time alone and liked working on projects on their own. They often say they felt like aliens in their family, as if plopped down from the sky into a family that was nothing like them.