The author demonstrates the art of meaningful engagement with adolescent clients from the outset of one-to-one work, highlighting how to attend to the nuances of contact to establish a trusting and supportive therapeutic alliance. Creativity is discussed, and the reader is introduced to Sandspace, a visual and three-dimensional manner of representing the adolescent’s lifespace, which amplifies the meaning-making process for the adolescent and encourages the development of contact. Impediments to the cultivation of an optimally supportive therapeutic space are discussed, including working in the presence of secrets and common therapeutic responses of urgency and despair. The author’s understanding of the differences between counselling and psychotherapy with adolescents are outlined.