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The Jungian Self as an archetypal force compensating chaos is explored through the author's personal experience with premonitory dreams and synchronicities at a time of loss, and is illustrated by two clinical cases and a tribute to Jung. The author sees this as an ultimate experience of the archetypal Self when, through an experience of darkness, loss, or death, we can comprehend the creative and the destructive as archetypal forces together. This was Jung's personal experience: born after his parents mourned the death of three siblings, his life force was overshadowed, as his early nightmares and thoughts centred on death and non-existence attest, leading him to his lifelong search for self and soul. His vision that “death is not the end but a coming together of two worlds. We are the bridge” invites us to apprehend the presence of the Self and the light of the soul in the midst of chaos, in our life and work. Even in cases of overwhelming trauma, as we witness now in violent conflicts raging at present, there is hope that a member of a future generation may work through transgenerational trauma to comprehend the creative and the destructive together in an experience of the Self: individuation can be seen as a wave spanning generations.