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From just getting by at the end of each month to getting ahead is a hard climb for low-wage workers, often requiring several steps, and the key to making sustained progress is to reach high enough to make sure that each step actually leads to financial gain. But because of the complex ways in which earnings interact with taxes and the phase-out of work supports (what economists refer to as “high marginal tax rates”), it is difficult for workers to anticipate whether a given advancement step pays. This report analyzes the interaction between earnings and the full package of work supports for different types of families and explores how career coaches in two of the sites — Dayton and San Diego — help low-wage workers understand and negotiate these complex interactions and guide them to make the best advancement decisions possible.