The goal of this paper is to determine whether or not multiple economic and societal changes have or have not made retirement in America, an easier, or harder goal to achieve. My hypothesis is that these changes have created an environment in which retiring and preparing for retirement is much, much more difficult. The analysis considers multiple economic and social changes between May, 1985 and May, 2019, a 34-year span. <br/><br/>In this paper, I will be comparing the average 1985 college graduate to the average 2019 college graduate. The 8 major factors I look at are, annual salary, average student debt (assuming a 120-month repayment period), average housing cost (assuming a 360-month payment period), average car expenses (assuming a 60-month payment period), and average annual food, clothing, taxes and medical insurance costs. All of these figures look at the end points, looking at figures for the average 1985 graduate, and the figures for the average 2019 graduate. The 1985 figures are then put into 2019 dollars, and subtracted from the original salary figure. This will give us an objective way to compare savings, and therefore ability to save for retirement. <br/><br/>My analysis demonstrates that it is actually easier for people today to prepare for retirement than it was 34 years ago. The average 2019 graduate had $4,178.96 remaining at the end of a year. Comparatively, the 1985 graduate had a debt of $12,837.94. This is an effective difference of $17,016.91, benefiting the 2019 graduate by far.