This qualitative study involved 54 individuals who were self-employed in a variety of solo businesses. All participants were administered a semistructured interview that inquired into various aspects of their work experience with the data subject to reliability and validity checks. The study identified stressful incidents, coping strategies, and emotional strains arising from those stressful incidents. Uncertainty about income was a common background stressor. Recent specific stressors included dramatic slowdowns in business, reputational threat, betrayal, unreasonable customers, and medical problems. Commonly occurring strains included apprehension/anxiety, frustration, anger, and sadness/depression. The self-employed used problem-focused coping much more often than emotion-focused coping. We also identified a third kind of coping that we labeled humanitarian coping. A number of questions/hypotheses for future research emerged, including identifying (a) a tipping point bearing on when the psychological benefits of self-employment (e.g., autonomy) are overtaken by business losses outside the individual’s control and (b) the coping strategies that are most useful in managing work-related stressors.