This recommendation comes from Josh Plattner. Check out his website and follow him on twitter @JoshPlattner.
The Empathy Exams (2014) by Leslie Jamison
Here Jamison offers us the chance to think more deeply about what it means to empathize with other people. Drawing on her work as a medical actor and personal experience of illness and injury, Jamison considers profound questions like "How should we care about one another?" and "How can we feel
another’s pain, especially when pain can be assumed, distorted, or
performed?" Her essays have appeared in Believer, Harper’s, Oxford American, A Public Space, and Tin House. The Gin Closet, Jamison's novel, came out in 2010.