In the context of incentivising farm afforestation to provide ecosystem services such as carbon sequestration to mitigate greenhouse gas production, this paper sheds new light on the complexity of the farm afforestation decision and the characteristics of the farms and the farmers who are likely or unlikely to afforest land. Using a panel dataset of farm level micro-data, we observe whether farming intensity changes as a result of planting. We generate forest and agriculture income streams and employ a life-cycle theoretical framework to analyse the relative importance of agricultural and forest financial drivers in the decision-making process at farm level. We find that for many farmers the afforestation decision involves a wider complex of contemporaneous farm decisions. We find that there is a relationship between financial drivers and the likelihood of planting but we also find that there is a cohort of older smaller farmers that will never plant, and for whom negative cultural attitudes are stronger than financial drivers. We also identify a cohort of large, younger farmers who might plant if the forest income is greater than the agricultural income. This paper describes the farm and farmer characteristics of these cohorts and concludes that a “one size fits all” programme based solely on financial incentives may not be the most appropriate means to encourage further farm afforestation.