Improving livelihoods and livelihood opportunities is a popular thrust of development investments. Gender and other forms of social differentiation influence individual agency to access, participate in, and benefit from existing, new, or improved livelihood opportunities. Recent research illustrates that many initiatives intended to improve livelihoods still proceed as “gender blind,” failing to account for the norms and relations that will influence how women and men experience opportunities and outcomes. To examine gender in livelihoods, we employed empirical case studies in three coastal communities in Solomon Islands; a small island developing state where livelihoods are predominantly based on fisheries and agriculture. Using the GENNOVATE methodology (a series of focus groups) we investigated how gender norms and relations influence agency (i.e., the availability of choice and capacity to exercise choice). We find that men are able to pursue a broader range of livelihood activities than women who tend to be constrained by individual perceptions of risk and socially prescribed physical mobility restraints. We find the livelihood portfolios of women and men are more diverse than in the past. However, livelihood diversity may limit women’s more immediate freedoms to exercise agency because they are simultaneously experiencing intensified time and labor demands. Our findings challenge the broad proposition that livelihood diversification will lead to improvements for agency and overall wellbeing. In community-level decision-making, men’s capacity to exercise choice was perceived to be greater in relation to livelihoods, as well as strategic life decisions more broadly. By contrast, capacity to exercise choice within households involved spousal negotiation, and consensus was considered more important than male or female dominance in decision-making. The prevailing global insight is that livelihood initiatives are more likely to bring about sustained and equitable outcomes if they are designed based on understandings of the distinct ways women and men participate in and experience livelihoods. Our study provides insights to make these improvements in a Solomon Islands setting. We suggest that better accounting for these gendered differences not only improves livelihood outcomes but also presents opportunity to catalyze the re-negotiation of gender norms and relations; thereby promoting greater individual agency.