Recently economists have shown that people who graduate during recessions earn less money (e.g., Kahn, 2010) and hold less prestigious jobs (Oyer, 2006) even decades after entering the workforce. This dissertation argues that despite these suboptimal outcomes, these graduates are likely to be happier with their jobs, even long after these economic conditions have changed. Four studies found that people who entered the workforce when the economy was sputtering and jobs were difficult to secure were more satisfied with their jobs than their peers who entered during better economic times, even decades after these early workforce experiences. Study 1 utilized a large cross-sectional national survey of working adults in the United States and found that college graduates who first looked for work during difficult economic times were more satisfied with their jobs well into their careers. Study 2 found that people who graduated from both college and graduate school during times of higher unemployment were happier with their jobs both early in their careers and years later, even when they earned less money. Study 3 replicated this effect in a different country, the United Kingdom, and among a more diverse educational population. Study 3 found that economic conditions at workforce entry predicted life satisfaction as well. Finally, Study 4 explored potential mediators of this effect and suggested that people who entered the workforce during economic downturns were less likely to entertain upward counterfactual thoughts about how they might have done better. This tendency fully mediated the relationship between workforce economic conditions and job satisfaction. While past research on job satisfaction has focused on dispositional and situational antecedents, these findings suggest that strong experiential factors also may have an enduring effect on how satisfied people are with their jobs.