<p>Cropping system diversification is widely promoted to address global challenges. However, its economic performance compared to high-yielding monoculture represents a major knowledge gap. Using a combination of grower focus groups and Monte Carlo simulations, this research assessed the required changes in farm management and profitability of transitioning from continuous rice (<i>Oryza sativa</i> L<i>.</i>) to tomato (<i>Solanum lycopersicum</i> L.), sunflower (<i>Helianthus annuus</i> L.), beans (<i>Phaseolus vulgaris</i> L.), and safflower (<i>Carthamus tinctorius</i> L.) in California. Long-term outcomes of rotation scenarios were explored to provide insights into economic barriers to adoption, including rice rotated with sunflower and tomato and rice rotated with safflower and beans. Two additional scenarios reflected agronomic benefits of rotation and potential for climate risk adaptation. This research provides evidence that crop diversification can increase profitability over the long-term. Yet to achieve this goal, policies and incentives are required to overcome barriers such as additional investment, risk, labor, opportunity costs, and market access.</p>