Introduction Patients with life-threatening disease should be informed about the diagnosis and prognosis of life-expectancy. Breaking bad news (BBN) by a clinician may be affected not only by their lack of communication skills but also their philosophy of life, beliefs, fear of their own death, their length of tenure, and their exposure to dying and death. Material and methods This questionnaire-based study aimed to investigate the impact of these factors on BBN in internal medicine practitioners (INT) versus palliative care physicians (PCP), and to detect the possible impediments to the proper communication process and the clinicians’ needs regarding their preparation for such a conversation. Results Thirty-eight PCPs and 64 INTs responded. Determination of philosophy of life, but not religiousness, positively correlated with the number of working years in palliative care. Two-thirds of the respondents declared fear of death, and it diminishes along with working years, especially in palliative care. For most physicians, BBN appeared difficult; however, less so for PCPs, persons with a high level of determination of philosophy of life, and men. The most frequent impediment was insufficient communication skills. Consistently, the respondents expressed the need for closing the gap in communication skills, especially by mentoring or training on communication. Conclusions Fear of death may restrain inexperienced medical professionals from BBN to patients and makes it difficult. Working in palliative care augments the determination of philosophy of life and diminishes fear of death. The higher the determination of philosophy of life, the more likely BBN is to be performed. Philosophy of life, spirituality, and communication skills should be addressed in postgraduate education.