The demographics, motivations, rewards, satisfaction, and commitment of Canadian career and later-life older entrepreneurs were examined. The two groups of respondents exhibited noteworthy contrasts. In terms of demographics, later-life older entrepreneurs were significantly less likely than career older entrepreneurs to be in management, and they were more likely to be female, unmarried, working alone, and engaged part-time. In terms of motivations, the career-long pursuit of entrepreneurship is strongly connected with the urge for independence; with a more singular approach to business, as registered by a significantly lower motivation for achieving work-life balance; and with higher values attached to start-up rewards, career success, and overall satisfaction with the business. By comparison, later-life older entrepreneurs focus significantly more on intrinsic rewards like work-life balance and achieving personal fulfillment. However, both groups posted high, statistically indistinguishable satisfaction with their businesses and commitment to self-employment.