This study developed a typology of eight heterogeneous types of baby boomer entrepreneurs and extended the occupational choice model regarding driving factors for entrepreneurialism in this population. The study relied on monthly USA Current Population Survey data across 11 years (2006-2016), and using 2-sample t-tests and multilevel mixed-effects logistic regression models that incorporated both individual- and metropolitan-level effects, found that "new" and "unincorporated" baby boomer entrepreneurs were more likely than their "continuing" and "incorporated" counterparts, respectively, to come from central cities, and that "continuing," "new opportunity," "full-time," and "incorporated" baby boomer entrepreneurs were more likely than "new," "new necessity," "part-time," and "unincorporated" baby boomer entrepreneurs, respectively, to be physically healthier and better educated. The typology and findings on USA baby boomers have global implications for career progression in older workers.