This is not true. As a Millennial, I know many people in my parents' generation who did well starting with a high school degree. They may have obtained further education later, but not at the beginning. This is borne out by statistics on post-secondary degree attainment by Boomers. The only exceptions were people who wanted to jump directly into professional work, like law or medicine, or, frankly, black people, who have always seemed to have to have an extra level of education to compete in the marketplace.