The reasons for success and well-being, and therefore of inequality, are numerous. A large number of systemic factors influence who succeeds or fails, who is healthy or sick. These factors, many of which are hard to understand or measure, interact in important and surprising ways. In contrast, humans tend to choose simple explanations of the world. Early humans evolved heuristics to help them effectively navigate a highly social, low-data world. Researchers choose intuitive, low-dimensional models of complex problems. While these approaches have provided humanity with tremendous benefits, they can sometimes fall short when faced with the systemic problems of the modern day. Technology plays a central role here, since tech can drive economic growth & improvements in health, as well as online polarization. This dissertation takes an interdisciplinary approach to examine the multifaceted nature of inequality in four studies. The first study presents a conceptual framework for the total effect of these factors on education, develops a novel statistical method, and uses administrative data to show universal patterns in community college students' ability to be successful. The second study is an experiment involving racially charged language that shows how individuals' tendencies toward simple explanations for inequality can combine with technology to create polarization and decrease open democratic discussion. The third study uses mathematics and statistics to develop a causal network model of multifactor cumulative (dis)advantage. The fourth study develops a conceptual framework for systemic inequality, and then uses models to explore the relationship between the causes of inequality and principles for designing effective interventions. [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.]