Work can be more than just a component of most individuals’ daily routines; it can influence how we feel and asses our lives. Moreover, career development is a process that tends to include different phases and transitions. Even individuals with highly stable career paths eventually transition into retirement. This study explores the relationship between work-life transitions and life satisfaction in seven European Union countries from 2011 until 2022, with a sample of individuals over 45. The data source of this analysis is SHARE, which stands for the Survey of Health, Ageing, and Retirement in Europe. The analysis drew upon the logic of Markovian Models (MM) to create a transition variable capturing changes between employment, self- employment, unemployment, and retirement. A panel data analysis is utilized for its advantages in controlling for unobserved heterogeneity and capturing dynamic relationships. The findings provide statistically significant evidence that transitions from unemployment to employment or self-employment, from self-employment to unemployment, and from retirement to self- employment display a positive association with life satisfaction compared to the reference category of transitioning from employment to retirement, which has implications for older adults’ well-being, labor-related and retirement policymaking in Europe.