The increasing speed of societal, environmental, technological, and workplace changes brings into sharper focus the question of how people shape and learn from transitions, such as so-called 'skilled migration'. Taking a doing transitions and doing migration perspective, I assert that transitions and migration do not simply exist but are constituted relationally through social practices and accompanied by learning processes. This paper reports findings from qualitative research into the question of how people learn and transform their understandings of (life)time when moving to a new country and seeking entry into the labour market. The study used the documentary method to analyse data from 20 biographical-narrative interviews with people who moved to Canada as adults. Findings indicate different modes of dealing with shifts in temporal contexts during migration as decompressing lifetime, losing time, and going with the flow. These modes are associated with positive transformative learning, negative transformative learning, and learning through participation in practices. This study has implications for theorising learning during life course transitions as a socially embedded process. It also points to the need for differentiated support as individuals seek to enter new labour markets or make career changes in the context of migration.