Drawing on literature highlighting persistent gender gaps across various stages of political careers, this study examines career dynamics within youth party organizations—the entry point for many politicians. Prior research indicates that women in youth parties are equally likely to aspire to non-electoral party positions but less likely to have the ambition to run for public office. This article investigates whether encouragement can close the gender gap in electoral ambition, whether women are equally likely to act on this ambition, and whether the source of encouragement influences outcomes. Using a broad-based self-collected survey of youth party members in Germany (2017-2018, n = 1293), the findings show that when actively encouraged to run for public office, women show the same electoral political ambition as men, and the gender gap in ambition disappears. Still, in some parties, women are still less likely to act on their ambition even after being encouraged. Lastly, encouragement by peers rather than parent party members seems helpful in increasing electoral political ambition. Examining these career dynamics is crucial for understanding and addressing the barriers to women's political participation within traditionally male-dominated (youth) party structures.