Across career development and academic advising literature, scholars describe a common and unsettling tension between when to challenge and support students' goals. Many programs of study include selective admission or gateway prerequisite courses. Students may also need to modify their goals while pursuing competitive employment or graduate school programs. As career professionals and academic advisors begin to perceive that students may not be able to achieve their aspirations, they may discuss different pathways and alternative careers. Some academic advisors use predictive analytics to identify students who may not progress within their chosen degree program, which further compounds the ethical dilemma. If practitioners do not engage in ethical inquiry and deliver feedback carefully, some students could experience distress or pivot away from their goals unnecessarily. As they discuss career alternatives, practitioners can consider the integrated literature review included in this article. Practitioners can use scholars' different frameworks and thematic recommendations to bring equity and ethical integrity to their career conversations.