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When scholars talk about pregnancy planning, a major national health goal in the United States, conversations often focus on proximate causes of unintended pregnancy – factors like reproductive health care interventions, birth control access and use, and sexual risk-taking. Less often studied is the broader, highly social phenomenon of what it means for couples, and women in particular, to plan a pregnancy. In this paper, I use 48 in-depth interviews to explore the incredibly common confusion, frustration, and uncertainty among women of reproductive age over how to 1) have the careers, relationships, and families they seek, 2) in the order they feel is best for themselves and their families, but 3) before they anticipate the decline of their biological fertility. I use their narratives to illuminate how factors like financial and relationship (in)stability create contextual barriers to family planning. Throughout, I highlight how inequality makes women’s ideal plans increasingly unattainable. For many, especially those facing socioeconomic hardship, figuring out a suitable life path, including when to have children, can seem insurmountable.