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American workers have witnessed striking changes in their jobs and wages during the last three decades. It is no longer simply a matter of growing income inequality, but increasingly deeper changes that go to the root of what it means to have a job and to build a career. Young workers are pessimistic about their chances for upward mobility and education no longer seems a guarantee of success. Workplaces are being restructured, creating anxiety about being laid-off and downsized. The recovery of the 1990s did not prove the cure-all that other recoveries have in the past, and disadvantaged groups in particular are being left behind. There is a growing sense that Americans are working under new rules. The very character of the American employment relationship appears to be changing - in how the workplace is organized, in how workers are matched with jobs, and in how wages and the terms of employment are set. This paper reports on a subset of findings from a larger study of the changes in job and wage mobility over the past 30 years. In this study, we compare two cohorts of young white men, from the National Longitudinal Surveys. The original cohort entered the labor market in the late 1960s at the tail of the economic boom, and was followed through the 70s decade. The recent cohort entered the labor market in the early 1980s after the onset of economic restructuring, and was followed through the early 90s. We observe both cohorts for a full 16 years, at exactly the same ages - respondents are in their late teens and early 20s at the start of the survey, and are in their mid-30s by the end. We can therefore compare the progress of the two cohorts during the initial stages of their careers, but under different economic conditions. It is during this period that workers make the transition from school to work, and lay the groundwork for an eventual long-term relationship wi th an employer. The key finding reported in this paper is that the transition to the labor market has become longer and more volatile. Young workers who do not go on to college are more likely to be intermittently unemployed and to rely on part-time jobs for a greater number of years. This is especially marked among high school dropouts. Those who do go on to college are more likely to work while enrolled and to significantly draw out the period of enrollment. For both groups, it takes longer to find a full-year job than it has in the past. The recent cohort is also less likely to make a single, clean transition to the labor market. Instead, these young workers are more likely to move back and forth between work, unemployment, enrollment, and non-participation. Workers at all levels of education have experienced this greater volatility, but it has been most pronounced among those with less education. There is noticeably more shifting between industries in the recent cohort, at all ages. Some of this is driven by deindustrialization and the shift to service industries, but not all of it. The greater volatility on these dimensions has taken its toll on the work experience that young workers accumulate. Average work experience is similar across the two cohorts. But there is considerably more variability in the amount of work experience that the recent cohort has accumulated, and this holds true across all education groups. Findings from the larger study indicate that this contributes to greater inequality in wages and wage growth for this cohort, trends that are likely to persist over their life course.