The article presents the results of research on the factors that determine how certain Czech millennials are about their housing and some other life aspirations. We did not primarily look at the content of life aspirations and instead, we examined how certain, confident and concrete young people are about their plans. Using qualitative interviews and an attitude survey we found that intergenerational housing-related within-family resource transfers had a significant impact on how certain young Czechs are about their housing and (some) work and family aspirations. Therefore, whatever the aspirations of young people are, the ability to form them with certainty and confidence is significantly influenced by a factor that is largely out of their control.