This paper studies how wealth affects workers’ ability to move to higher-paying jobs. Using microdata from the SIPP, I compare equally skilled workers in similar careers and find that those with higher liquid wealth are, on average, 1.15 percentage points more likely to change jobs than workers with no savings, especially at the bottom of the job ladder. To explain these patterns, I develop a job ladder model with incomplete markets, risk-averse workers, and wage posting. If firms learn about workers' quality over time and fire those who turn out to be poor matches, on-the-job search becomes risky: wage increases come at the cost of restarting the learning process and facing a higher risk of job loss. To avoid this risk, workers with no liquidity prioritize job security over job mobility and remain trapped in low-paying jobs. However, higher replacement rates and extended unemployment benefits increase job mobility especially for poor workers at low-paying jobs, offering a potential pathway out of the job trap.