The paper presents dilemmas and difficulties that a psychotherapist may encounter when faced with his or her own illness, which makes it more difficult or even impossible for him or her to carry on psychotherapeutic processes in the way they were carried up to that moment. It pertains to situations which often require modification in usual practices and arrangements made with patients. Sometimes it requires innovation and breaching of some conventions. Ailing of a psychotherapist makes itself present not only in the therapist’s mind but reveals itself in the therapeutic relation with a patient and affects patient’s experiencing of psychotherapy and of him/herself in relation with therapist. Psychotherapist’s illness and its possible consequences for the treatment are related to the question of therapist’s self-disclosure. The psychotherapist is responsible for deciding when, how, and to what extent disclose these circumstances and its potential impact on the course of psychotherapy to the patient. Drawing on our own experiences and literature of the subject, we are aiming in this work to delineate and underscore some conditions that may take place during psychotherapy, including the external reality domain, subjective world of experience and the intersubjective relational domain. We suggest to conceive of these moments as possibly critical ones, that embrace some risks and chances for facilitating a change altogether. Therefore, our ultimate aim in this paper is to put in motion thoughts and second thoughts based on these conditions. The work contains some literature review and ideas from our own psychotherapeutic and supervisory work.