The goal of teaching is student success, but defining success can be daunting. A rudimentary description of student success involves academic achievement and students’ attainment of a high level of satisfaction with their educational process. The pinnacle of student success is transformational learning. Transformational learning is ultimately evidenced by knowledge-based, responsible, and autonomous thinking. Student engagement enhances student success. As a result, course design and assignment design are critical. The purpose of this paper is to demonstrate how an online discussion assignment can be used to enhance student engagement and increase student success in a university class. The assignment presented in this paper was used in three sections of Global Environment of Business classes in 2021. We designed it to be more than a simple transactional assignment. For the discussion assignment, students were required to address the following: “Should society adopt capitalism or socialism as an economic system? Why?” Students were presented relevant information and were required to think critically about the topic, write their thoughts on a discussion board, and respond to their peers. Then, the instructors evaluated students’ comments, sought to understand their perspectives on the topic, and followed up with appropriate materials in subsequent classes. The coursework moves students toward transformational learning. The assignment requires students to present new information, reflect critically on their point of view, consider the applications of what they have learned, and, finally, think responsibly and autonomously, which is the goal of transformational learning.