Research indicates that entrepreneurs are relying on digital technology for their entrepreneurial endeavours, yet there is little knowledge on how to balance technology usage and wellbeing. Drawing on the concept of technostress and 643 observations of nascent South African entrepreneurs’ interactions with digital technology, we advance knowledge at the technostress–entrepreneurship nexus. Partial least squares structural equation modelling (PLS-SEM) results reveal how digital self-efficacy moderates their behaviour and inability to balance digital technology usage with wellbeing. These results confirm entrepreneurship passion and perceived behavioural control as predictors of technostress amongst these entrepreneurs. They also suggest that the benefits of digital technology are not a predictor of technostress in African entrepreneurship; thus, extending a conceptual overlay of digital technology, digital self-efficacy, entrepreneurial passion (EP), and behaviour to define the mechanisms underlying a technostress–entrepreneurship nexus. The results show social, policy, and research implications in today’s technology-driven environments characterised by a mixture of midrange to complete digital transformations.