The growing importance of entrepreneurship and the constrained influence of business environments in most parts of developing countries have necessitated the call for an appropriate institutional framework for explaining entrepreneurial behaviours. Institutional structuralism holds that entrepreneurship development is shaped by prevailing framework and rules that govern the business environment. On the other hand, within the context of institutional individualism embedded in the agency principles, entrepreneurship development is rather viewed as an outcome of individual tendency for profit maximization. By extension, the neo-institutional approach emerges as a framework for explaining the inherent paradox of embedded agency – that is, the entrepreneurs’ inability to undertake institutional transformation even in the presence of constraints. In this chapter, we make use of the three-pillar institutional framework (the regulative, the normative, and the cognitive) developed by Scott (2004) to explain how entrepreneurial development is moderated or promoted by institutional complexities. We draw on the three pillars to illustrate the context dependent nature of entrepreneurship in a developing society such as Nigeria. The key prescription from our analysis is the need to rethink entrepreneurship development not merely driven by individual free choice, but more as an outcome of wider contextual factors that create opportunities and barriers for individual career development.