Ambition and risk-taking have been heralded as important ways for marginalized communities to get out of cycles of poverty. As a result, educational messaging often encourages individuals to strengthen their personal resolve and develop characteristics such as discipline and grit to succeed in ambitious ends. However, recent work in philosophy and sociology highlights that this messaging often does more harm than good for students in these situations. We study similar questions using a different epistemic approach and in simple theoretical models -- we provide a quantitative model of decision-making between stable and risky choices in the improving multi-armed bandits framework. We use this model to first study how individuals' "strategies" are affected by their level of grittiness and how this affects their accrued rewards. Then, we study the impact of various interventions, such as increasing grit or providing a financial safety net. Our investigation of rational decision making involves two different formal models of rationality, the competitive ratio between the accrued reward and the optimal reward and Bayesian quantification of uncertainty.