In our modern society, self-reflection is valued as an important tool to work on a positive and lasting self-identity and to find and define our own path in life. Self-reflection can be seen as the fruit of the scientific approach, which has taught us to divide reality into subject and object. The reflecting person looks at him- or herself as an object that can be observed and analysed in order to reach a conclusion. However, this division between human and nature, and between the person and him- or herself, can also be a source of alienation and depression, because it fractures a more primitive connection between the self and nature. The article documents a coaching workshop that seeks to restore, to an extent, the undivided self in unity with nature. To do so, it uses the fairy tale of Little Red Riding Hood, a story that stems from a time long before the rise of objective thinking and cognitive reasoning. It presents a method that combines the telling of the fairy tale, walking in a forest with old oaks, and talking about life events. Twelve participants, all career counsellors, take part. Their reflections demonstrate that through connecting the walk in nature with our absorption into the fairy tale, we are able to accomplish a state of second primitivity where cognitive control and reflective observation temporarily give way to sensitivity, vulnerability, and susceptibility to the symbolism that is linked to pre-reflexive experience. The interplay between the symbolism of the fairy tale, the lived story of the walking experience in the woods, and the mutual storytelling between the participants enhances the emergence of new insights and new (self-)acceptance.