The business environment in Nigeria is characterised by significant systemic challenges, yet many enterprises demonstrate notable resilience. Existing literature often quantifies these obstacles but lacks in-depth qualitative analysis of the lived experiences and adaptive strategies of business leaders navigating this complex landscape over an extended period. This study aims to qualitatively explore the key systemic challenges perceived by Nigerian business leaders and to analyse the strategic resilience mechanisms they employ to sustain operations and achieve growth. A qualitative, multi-case study design was employed, using purposive sampling to select 32 senior executives from diverse sectors. Data were collected via in-depth, semi-structured interviews and analysed using a thematic analysis approach to identify core patterns and strategic themes. Analysis revealed three dominant, interlinked systemic challenges: infrastructural deficiencies, regulatory unpredictability, and pervasive informal rent-seeking. A key theme was that over 80% of participants framed regulatory unpredictability, not corruption per se, as the primary constraint on strategic planning. Resilience strategies were predominantly relational, relying on embedded informal networks for information and resource mobilisation. The findings illustrate that strategic resilience in this context is less about formal contingency planning and more about the dynamic cultivation and leverage of socio-political capital to mitigate systemic volatility. Policymakers should prioritise regulatory clarity and consistency over anti-corruption campaigns alone. Business support programmes should facilitate formalised peer-networking platforms to help firms institutionalise effective informal resilience practices. Business environment, strategic resilience, qualitative study, systemic challenges, institutional voids, Nigeria This paper provides a novel, empirically-grounded framework of 'relational resilience', demonstrating how firms strategically navigate institutional voids by converting social capital into operational buffers, thereby advancing behavioural finance literature on decision-making under non-market constraints.