Students who choose to enter college in their twenties, thirties, and beyond face the challenges of balancing their academic experiences with busier lives, often with little social capital to guide them through the intricacies of college life. Students may feel overwhelmed, easily discouraged, or overlooked by people within their institution, including their professors. Instructors who, themselves, lack the experience of being first-generation college students may struggle to identify with the behaviors of the students they teach. They may see their roles as evaluators more than as partners or guides. The practice of compassionate grading and teaching can increase opportunities for trusting relationships to form among instructors and students, and for learning to occur.