Designers are skilled at creating an ideal experience for idealized users. But what happens when our idealized experience collides with messy, human reality? Designs can frustrate, alienate, or even offend; form options can exclude; on-boarding processes can turn away; interactions can reject or even endanger. The more we build websites and digital products that touch every aspect of our lives, the more critical it becomes for us to start designing for imperfect, distressed, and vulnerable situations—designing interfaces that don’t attempt to make everything seamless, but instead embrace and accommodate the rough edges of the human experience. In this talk, Eric will explore a wide variety of failure modes, from the small to the life-changing, and show how reorienting your perspective and making simple additions to your process can help anticipate and avoid these failures, leading to more humane, and ultimately more compassionate, outcomes.