In 2017, the authors began research for a book that would suggest training needs for the U.S. and Canadian workforce in the coming decades. Early in the research process they realized there was much more to understand in an evolving workplace than the call for reskilling workers. Workers would face many decisions influencing their careers while the structure of work changed and the social contract with workers weakened. A review of literature with a special focus on 2017-2020 revealed several broad categories of change that have begun across most industries and affect middle-skilled and highly skilled workers. Among trends identified from this research, this article discusses three topics to consider including in education and training (E&T) program content: (1) understanding automated job search and selection processes, (2) evaluating workers' responsibility to continually upgrade job skills, and (3) achieving financial wellness.