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Self-esteem plays a significant role in an individual’s healthy development. However, it is not uncommon for Chinese people to suffer from lower self-esteem. The cultural expectation of respect for and obedience to authorities often increases the challenges for Chinese people to achieve individuation. Subjectivity of being and the authenticity of a true self is ignored and even must be renounced in order to fit oneself into the cultural and societal system. What can psychotherapy do to enhance self-esteem? Psychoanalytic psychotherapy provides a way for individuation through enhancing realistic self-esteem. In the psychoanalytic and psychodynamic situation, patients’ individuality is encouraged. Moreover, it provides a new relationship where ruptures can be dealt with for the purpose of personal growth. Self psychology will be the theoretical foundation for this paper to illustrate that enhancing realistic self-esteem can a be a maturational step for individuation in working with Chinese patients. Two cases are presented to illustrate how psychoanalytic psychotherapy can help with self-esteem. Both cases involve young Chinese people struggling with damaged self-esteem. In the first case, I will focus on how interpretations can help the patient gain insights and to encourage further exploration. In the second case, I will write about how realistic self-esteem can be gradually gained through working primarily in the transference.