This is a theoretical consideration of a dilemma posed in 2016 by Richard Brouillette: How should psychotherapy approach the issue of clients whose distress originates with difficult life conditions? After the problem is introduced and research area charted, Chapter 2 assesses what can be gleaned from psychotherapeutic discussions of psychopathology relating to the DSM and psychoanalytic diagnostics. Brouillette’s dilemma also raises questions of “normality” (is Brouillette’s client “normal” in the sense of mentally healthy? Are her working conditions normal?), thus this notion is interrogated in Chapter 3, referring to the Rosenhan Experiment, Allen Frances and Erich Fromm. Chapter 4 provides psychosocial perspectives, like the potential for the vulnerability-stress hypothesis to conceptualise psychotherapeutic challenges, and David Smail’s social materialist psychopathology. The conclusion plots future research trajectories.