Farmer-led irrigation is valued for its resilience and ability to cope with shocks and benefit from opportunities. Yet, typologies of farmer-led irrigation are mostly static categorisations without analysing farmers’ decision-making over time, and without studying ‘failed’ cases. We therefore analysed temporal changes in farmers’ irrigation strategies to expand, downscale or cease practices as part of wider livelihood decisions and aspirations. This longitudinal study presents irrigation trajectories of 32 farmers in the arid lands of two contrasting socioeconomic settings in Kenya and Zimbabwe. Data were collected through multiple rounds of surveys and in-depth interviews. Results show that farmers frequently alternated strategies or ceased or restarted operations over the years, both by force and choice. Although many farmers were able to start, expand or sustain irrigation, not all managed or aspired to remain engaged in irrigated farming, even if the enabling environment was conducive for market-oriented irrigation development. We therefore conclude that farmers’ needs cannot always be expressed in general terms of growth or commercial farming, nor can they always be satisfied by improving the enabling environment, which may be based on static ontologies of diverse types of farmers.