The whole idea of Separation-Individuation already begins from our childhood and keeps happening throughout our life in different stages. In the very early stage the child begins to discover that he or she is different from the mother and begins to separate and begins to assert its individuality. Once in school, the child begins to experience connecting with other individuals recognizing the differences in each other. In teenage years one begins to individuate further from the family ties while still retaining them in spite of conflicts in many cases. But because there has not been enough preparation and healthy learning in the process, we see that many adults face chaos and challenges in their lives and feel that they are incapable of coping with stresses and experience a certain level of helplessness and loneliness. All my clients in the case analyses presented in this paper manifest a deprivation of healthy individuation process and as a result the inability to build healthy relationships or make the right choices and bear responsibility for those choices. Although every client is unique in their own situation, all of them struggle to untie their emotional bond with their parents or caregivers either because of overprotection or through lack of secured attachment that led them to wander with an emotional breakdown. In Case 1 there is a struggle in the development of emotional autonomy. In Case 2 there is a struggle in the development of both cognitive and functional autonomy. In Case 3 there is a struggle in the development of emotional autonomy. In case 4 there is a struggle in the development of emotional and cognitive autonomy in the process of individuating. Similar separation process happens even among friends when they have to leave each other due to situations of life or because of conflicts and negative experiences in their life. Further individuating takes place when couples decide to divorce and have to go through hard times of separating from long years of relationship. And it takes boldness and courage to move on in life finding separate ways to live and find meaning in their lives. In order to accomplish this, one needs to have a strong ego and inner self that possesses self-esteem and self-regulating mechanism.