Purpose: This study investigated the distinctiveness of two types of heavy work investment (i.e., workaholism and work engagement) by examining their 2-year longitudinal relationships with employee well-being and job performance. Based on a previous cross-sectional study by Shimazu and Schaufeli (Ind Health 47:495–502, 2009) and a shorter term longitudinal study by Shimazu et al. (Ind Health 50:316–21, 2012; measurement interval = 7 months), we predicted that workaholism predicts long-term future unwell-being (i.e., high ill-health and low life satisfaction) and poor job performance, whereas work engagement predicts future well-being (i.e., low ill-health and high life satisfaction) and superior job performance. Method: A two-wave survey was conducted among employees from one Japanese company, and valid data from 1,196 employees was analyzed using structural equation modeling. T1–T2 changes in ill-health, life satisfaction, and job performance were measured as residual scores, which were included in the structural equation model. Results: Workaholism and work engagement were weakly and positively related to each other. In addition, and as expected, workaholism was related to an increase in ill-health and to a decrease in life satisfaction. In contrast, and also as expected, work engagement was related to increases in both life satisfaction and job performance and to a decrease in ill-health. Conclusion: Although workaholism and work engagement are weakly positively related, they constitute two different concepts. More specifically, workaholism has negative consequences across an extended period of 2 years, whereas work engagement has positive consequences in terms of well-being and performance. Hence, workaholism should be prevented and work engagement should be stimulated.