Who is able to overcome adversity and experience upward mobility? Using cumulative inequality theory, which posits that the disadvantage or advantage associated with one’s social location impacts life trajectory and perceptions of such, I propose that level of optimistic outlook in individuals from low-income backgrounds increases their chances of financial success in adulthood. Analyzing data from the 2016 General Social Survey, a nationally representative survey administered to randomly sampled adults in the U.S., I examine a subset of 1,269 individuals from backgrounds of far below average or below average family income levels. In doing so, I determine how optimistic attitudes, regarding matters such as personal agency and success, influence whether the individual may obtain a higher degree of financial success in adulthood compared to those of their families. Findings indicate that higher levels of optimism are associated with greater family income levels, with level of education and marital status as the biggest predictors of adult financial standing. With higher educational attainment, optimistic outlook increases, perhaps due to an increase in career opportunities and pathways to success. These findings show how influential education may be on intergenerational income mobility, however, they also provide insight on how disadvantage, including being a person of color; being divorced, separated or a single-parent; as well as how many children one has, may create limitations on educational attainment and effects on outlook. Such findings call attention to the need for greater financial and educational assistance programs, due to their impact on outlook and subsequent life course.