Freelancers are professional, skilled, self-employed workers who are dependent on intermittent projects from various clients to generate income. The growing popularity of freelancing has raised several organisational and sociological issues.

First, the exemption from managerial authority distinguishing freelancers from permanent organisational employees is associated with autonomy and flexibility, which in principle should be conducive to meaningful work experience. While the work meaningfulness literature shows how employees craft jobs and change work boundaries to make work meaningful, this thesis investigates how freelancing leads to meaningful experience in the absence of those work boundaries.

The narrative of autonomy has been contested by the argument that freelance work is subject to market imbalances making it exploitative. Labour process analysis regards freelancers as exploited workers, but this analysis risks neglecting the subjective level of experience. From the perspective of moral economists, exploitation is subjective, which raises the second question: do freelancers perceive their work to be exploitative or non-exploitative?

The third question addresses differences in cultural norms. Freelance relations are contractual; without collective representation, freelancers are responsible for negotiating terms of work with clients. Because interactions between contracting parties occur in a cultural context, these interactions may differ.

To explore the three questions above, interviews with freelancers from various professions in England and Taiwan were conducted and analysed. The findings demonstrate that 1) despite the constraint of stabilising income, freelancing affords the freedom of exploring and maintaining meaningful experience; 2) freelancers refer to clients’ bargaining power and other moral considerations to assess whether they feel exploited; 3) England and Taiwan differ in contract negotiation and freelancers’ reactions to contract violations. Collectively, this thesis contributes to the understanding of freelancing as a means to achieving meaningful experience, and of freelance relations as socially embedded interactions influenced by cultural norms.