The social entrepreneurship literature largely focuses on internal practices for managing social and commercial goals, implicitly assuming a relatively stable external environment. Considering the struggles of many social enterprises in economic downturns, we investigate how social enterprises manage to survive and grow in the long run, or fail to do so, in changing macroeconomic conditions. Through a qualitative study of a fair trade social enterprise that operated for 55 years (1965–2020) in Canada, we identified two distinct approaches to growth: relation-based and expansion-focused approaches. While expansion-focused approaches enabled the social enterprise to generate greater impact in favorable macroeconomic conditions, they aggravated financial challenges in economic downturns. In contrast, relation-based approaches led to only modest growth yet provided a source of long-term endurance through community-based assets and relationships, even in the aftermath of major economic recessions. By conceptualizing different approaches to the growth of social enterprises and their far-reaching implications, we contribute a novel understanding of the long-term survival and growth of social enterprises in evolving macroeconomic contexts.