This correlational research study examined simultaneously the following, with regards to the outcome variable of whether students fulfilled their educational expectations 8 years after graduating high school across a nationally representative sample of participants: (1) the extent to which parents' academic expectations predict students' fulfillment of expectations, (2) how risk factors and academic self-efficacy interact with parents' academic expectations in predicting students' fulfillment of expectations, and (3) how the interactions between parents' expectations and the variables of academic risk factors and academic self-efficacy were moderated by instrumental or extrinsic motivation in predicting expectation fulfillment. Controlled variables included race, gender, and socioeconomic status. The data source was the Educational Longitudinal Study of 2002. Results from binary logistic analyses indicated that when all predictor variables and interactions were included in the model, neither instrumental motivation, academic self-efficacy, number of academic risk factors, nor parental expectations were significant predictors of educational expectation fulfillment. Those most likely to fulfill their expectations had zero risk factors and low parental expectations. The study's contribution to the literature lies mostly with determining predictors of the unique outcome of educational self-actualization rather than the societal expectation of high educational attainment. An implication of the study is for educators, administrators, and parents to help students develop realistic and attainable goals. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]