Land degradation poses a major threat to agricultural production and food security in Ethiopia, and sustainable land management (SLM) is key in dealing with its adverse impacts. This paper examines the covariates that shape rural livelihood diversification and examines their effects on the intensity of adoption of SLM practices. Household-level data were collected in 2017 from 270 households in three drought-prone watersheds located in northwestern Ethiopia. We used the Herfindahl–Simpson diversity index to explore the extent of livelihood diversification. A stochastic dominance ordering was also employed to identify remunerative livelihood activities. A multivariate probit model was employed to estimate the probability of choosing simultaneous livelihood strategies, and an ordered probit model was estimated to examine the effect of livelihood diversification on the adoption intensity of SLM practices. In addition to mixed cropping and livestock production, the production of emerging cash crops (e.g., Acacia decurrens for charcoal, and khat) dominated the overall income generation of the majority of farmers. Stress/shock experience, extent of agricultural intensification, and agro-ecology significantly affected the probability of choosing certain livelihood strategies. Livelihood diversification at the household level was significantly associated with the dependency ratio, market distance, credit access, extension services, membership in community organizations, level of income, and livestock ownership. A greater extent of livelihood diversification had a significant negative effect on adopting a greater number of SLM practices, whereas it had a positive effect on lower SLM adoption intensity. Overall, we found evidence that having greater livelihood diversification could prompt households not to adopt more SLM practices. Livelihood initiatives that focus on increasing shock resilience, access to financial support mechanisms, improving livestock production, and providing quality extension services, while also considering agro-ecological differences, are needed. In addition, development planners should take into account the livelihood portfolios of rural households when trying to implement SLM policies and programs.