Global environmental change is pushing many socio-environmental systems towards critical thresholds, where ecological systems' states are on the precipice of tipping points and interventions are needed to navigate or avert impending transitions. Flickering, where a system vacillates between alternative stable states, is touted as a useful early warning signal of irreversible transitions to undesirable ecological regimes. However, while flickering may presage an ecological tipping point, these dynamics also pose unique challenges for human adaptation. In this work, we link an ecological model that can exhibit flickering to a model of human adaptation to a changing environment. This allows us to explore the impact of flickering on the utility of adaptive agents in a coupled socio-environmental system. We highlight the conditions under which flickering causes wellbeing to decline disproportionately, and explore how these dynamics impact the optimal timing of a transformational change that partially decouples wellbeing from environmental variability. The implications of flickering on nomadic communities in Mongolia, artisanal fisheries, and wildfire systems are explored as possible case studies. Flickering, driven in part by climate change and changes to governance systems, may already be impacting communities. We argue that governance interventions investing in adaptive capacity could blunt the negative impact of flickering that can occur as socio-environmental systems pass through tipping points, and therefore contribute to the sustainability of these systems.