The COVID-19 pandemic has radically altered how we learn, work, and live. This qualitative research aimed to study the effects of the COVID-19 pandemic on the educational and occupational aspirations of young Canadian adults. All close to 29 years of age, sixteen participants took part in one-on-one semi-structured interviews conducted through Zoom. Questions probed participants’ hopes, dreams, and perceived obstacles regarding school and work. Coding was completed using the research software Dedoose. Thematic content analysis was performed using both deductive and inductive approaches. Three themes emerged: the benefits and drawbacks of working and learning from home; financial changes and concerns; and hope and optimism despite challenges posed by the pandemic. Working and learning from home were discussed by 88% of participants, making it the most prominent theme. Participants generally agreed that working and learning from home had many benefits, but some expressed concern about the quality of online education. In addition, the pandemic caused financial hardship for a few participants, forcing them to delay educational or occupational plans. However, the majority (75%) expressed positivity and hope for the future. Overall, although the timeline of some participants’ educational or occupational plans changed, their aspirations largely remained the same.