In response to the question posed in this special issue of the "Journal of Career Assessment" regarding the next big question in vocational psychology, this article poses that the field is at a critical fork in the road. The choice point for vocational psychology is to continue to create knowledge and services for middle-class populations with some degree of choice in their lives or to expand our inclusiveness to include people without as much volition about education, training, and work. In advocating for the road less traveled, some of the challenges and benefits that may result from examining the work lives of the poor and unemployed are reviewed. Selected contributions that vocational psychology can add to the discourse in unemployment and poverty are outlined.