One of the most difficult parts of working with students that are struggling with mental illness, income instability, and racism is balancing empathy for the challenges they face with high expectations. Questions such as, “Is it fair to expect students who lack basic essentials to have completed their research paper?” or “Should I require homework, if many of my students don’t have a place to do their homework?” are asked by the reflective educator. Finding a balance between high expectations and empathy can be especially difficult. It can be easy to blindly hold all students to the same standards, but, on the other hand, in the name of empathy, we may be inclined to “give the kid a break.” However, in the long run, these “breaks” can become learning gaps. Finding this balance requires much trial and error, plus a deep knowledge of and connection with each student.