Millions of people around the world survive critical illness each year only to realize that they and their loved ones are grappling with a new "normal" after hospital discharge for which their medical team may not have adequately prepared them. Up to half of all intensive care unit (ICU) survivors suffer from new or worsening impairments in physical, cognitive, and psychological domains of health that are often not realized until they attempt to re-enter their previous lives. These devastating long-term sequelae of critical illness, collectively described as the Post Intensive Care Syndrome (PICS), can carry enormous consequences for an ICU survivor's ability to care for their family, return to work, and regain their previous quality of life for months to years after their inciting illness. Despite mounting research on PICS and survivorship, a knowledge gap exists whereby ICU team members may not always be aware of PICS and may not counsel their patients on the challenges awaiting them after discharge. Understanding how best to communicate these challenges to patients and families is crucial in preparing for survivorship beyond the ICU. In this review, we summarize PICS and possible recovery trajectories of ICU survivors. We then discuss communication strategies, emphasizing the role of empathy. Finally, we provide a suggested framework to handle these crucial conversations. We aim to equip clinicians with the knowledge and framework to care for a patient who has survived critical illness but now faces the possibility of struggles inadequately addressed by our health care system.