Uganda's transition toward a knowledge and technology-driven economy demands a critical examination of whether its environmental conditions adequately support the changing nature of work — a shift commonly described as moving from working hard to working smart. This study assessed Uganda's environmental readiness for the changing nature of work, with particular focus on digital infrastructure, workforce skills capacity, and policy frameworks. Employing a cross-sectional survey design, data were collected from 385 workers across six economic sectors in Uganda. Univariate analysis revealed moderate to low readiness across all three environmental dimensions. Bivariate correlations demonstrated statistically significant and strong associations between digital infrastructure, workforce skills, and smart-work readiness (r = 0.641, 0.587, and 0.489 respectively; p < 0.001). Structural Equation Modelling (SEM) confirmed that digital infrastructure was the strongest direct predictor of smart-work readiness (β = 0.421, p < 0.001), followed by workforce skills capacity (β = 0.383) and the policy environment (β = 0.274). Smart-work readiness, in turn, significantly predicted economic productivity (β = 0.512) and labour market transformation (β = 0.441). Sectoral analysis revealed a stark digital divide, with the ICT sector exhibiting the highest readiness (71.2%) and agriculture the lowest (18.4%). The study concludes that Uganda's environmental readiness for smart work remains critically insufficient, and recommends targeted investment in digital infrastructure expansion, skills upgrading programmes, and enabling policy reforms to accelerate an inclusive transition to the future of work.