The arrival of Generation Z, the next generation of medical learners, has been accompanied by efforts to adapt teaching practices for this new group of students. Many have identified challenges associated with addressing the needs of modern medical learners. One particular trend we have observed is that medical students are increasingly requesting an “answer key” for all aspects of their medical education. Students often expect to have the correct answers readily available to them to ensure they have reached the correct conclusion and to determine the precise knowledge they need to master. Yet, for much of medicine, and particularly in the care of critically ill patients with multisystem disease in intensive care units, answers are uncertain, and the body of knowledge is ever-growing. Students’ regular requests for solutions to be provided to them threaten to undermine their development into critically thinking, self-sufficient physicians. We outline three potential contributors to this multifactorial problem and offer corresponding pedagogical solutions. Specifically, we address how prioritizing outcomes over process, discomfort with uncertainty, and fear of faltering can cause students to seek excessive levels of support that may ultimately do more harm than good. Addressing students’ concerns in these three key areas will not only serve students well during their undergraduate medical training but will also equip them with the skills needed to succeed in the clinical realm. To produce physicians capable of navigating an increasingly uncertain world, medical educators will need to help students appreciate that finding the answer is more complex than being provided an answer key.