Personality can play a large role in dispersal decisions, influencing how each individual estimates and values expected costs versus benefits of venturing out to explore the unknown. We contrast the impact of persistence on fitness using decision theory models to examine the relative success of prospecting movement (which is a widespread behavior used by animals to explore available breeding habitat before determining where to settle) in different landscapes among individuals with different personalities. While evaluating trends in the costs and benefits of movement we provide a quantifiable measure of the impacts of relative tenacity in prospecting behavior on fitness gains/losses. Our model results predict that, regardless of landscape composition, individuals with greater tenacity in prospecting strategy have reduced fitness gains relative to individuals who are more willing to both initiate novel strategies, but then also abandon the new strategy rapidly if initial search does not seem fruitful. We show that fitness gains from choosing an appropriate prospecting strategy (i.e. abandoning poor habitat or staying in rich habitat) can be very high, indicating a potentially large influence from personality on fitness. Importantly, the model predicts that relative fitness gains are highly dependent on the availability of high quality habitat in the landscape, even if the difference under varying fitness outcomes between poor and rich habitat was substantial.