This article accounts for a renovation by enriching the existent literature regarding two major nowadays phenomena and their labor implications, which might require a rethinking regarding new career-development approaches: the overeducation phenomenon (academic graduates whose educational level exceeds the educational level required in their jobs) and the horizontal-mismatch phenomenon (the individuals’ fit between their educational and occupational fields). The article clarifies the difference between those two phenomena’s career repercussions—on three major individuals’ career outcomes: wage gaps, job mobility, and demand for further higher education. Two hundred and twenty-one participants took part to reveal that the more the individuals experience horizontal mismatch throughout their career, the less their earning level is, and the horizontally mismatched individuals have lower probability for pursuing further higher education compared to the horizontally matched individuals. These findings’ implications suggest individuals to try and modify their career planning, based on the ongoing technological and structural changes in Western-developed countries labor market.