A pandemic, trade frictions (e.g., tariff escalations), or nationalism can dial back global integration as much as advancements in IT and transportation can spur it. We study a parsimonious general equilibrium model of occupational choice, risk-taking, and income inequality against the backdrop of market (dis)integration and certain services in inelastic supply over the short run. In a decentralized, segmented environment, entrepreneurship and risk-taking are inefficiently low; in an integrated market, they can be socially excessive and entrepreneurship is non-monotone in the service supply. As transportation and information technologies improve, occupational risk-taking and total production increase, with ambiguous welfare consequences. In a dynamic setting with inter-generational inheritance, wealth inequality is exacerbated by income inequality, but faces a long-term reversal when total production helps increase service supply. Our findings are generally robust to endogenous service supply and various levels of scarcity.