This research utilizes the National Financial Capability Study (NFCS) funded by the FINRA Investor Education Foundation. The national and state-level data are extracted from the 2015, 2012 and 2009 NFCS State-by-State Surveys, each of which employed nationwide online surveys of over 25,000 American adults. This survey solicits information from individual investors on retirement and non-retirement account investments, actual level of investment sophistication, and self-perceived level of investment sophistication, along with many demographic variables. This study investigates the relationship between actual and perceived investor sophistication to determine retirement preparedness of investors, as well as whether investors understand their level of financial preparedness. It is hypothesized that most investors are not as prepared for retirement nor as sophisticated investors as they believe. Additionally, it is hypothesized that there will be a difference in results related to age, education, and gender.