Now that the capabilities of medicine provide increasingly complex care and technology to keep patients alive in health states they might not desire, the clinician is responsible for anticipating future care needs and guiding treatments as patients become more ill and less functional. Advance care planning is an essential tool in the primary care practitioner’s armamentarium, and this skill set must be honed to ensure that patients receive care consistent with their informed preferences and appropriate to their prognosis. Clinicians must feel comfortable introducing advance care planning, carrying out serial discussions with patients about prognosis, using appropriate tools and practice structures, and coordinating care among the team of clinicians caring for their patients across care venues. Sometimes the process requires setting limits and addressing maladaptive coping. Building strong relationships with patients and families and a consistent focus on goals of care is key to high quality treatment for the complex patient and achieving optimal end of life care.