In response to survival challenges, small farms in the United States undertake decisions to minimize downside risk or maximize gross revenue. Using primary survey data of small farms in Tennessee, we examined farmers’ strategic decisions on specialization or other forms of diversification and estimated the impacts of these decisions on farm financial performance. We found that farmer’s age, farmland holdings, use of a smartphone in farm-related activities, and off-farm work significantly influenced these strategic decisions. Our multinomial endogenous switching regression estimates suggested that small farms could attain significantly higher performance, around 45% higher gross farm income and a 30% higher return on assets, by adding alternative on-farm enterprises.