The paper considers the structural and subjective factors shaping patterns of labour market participation of lone parents around the transition to parenthood by adopting a life course perspective and a mixed-method approach. The multiple roles of primary caregiver and breadwinner and the connected responsibilities are handled differently by lone mothers depending on both individual and household characteristics. Drawing on the Swiss Household Panel data on lone parents work trajectories (N=561), we detect five employment pathways around the transition to lone parenthood. Young age and a higher educational level are favourable to arrange engagement in paid work and conciliate the trade-off between care and income need. The analysis of semi-structured interviews (N=38) sheds lights on the rationales beyond differences and the interaction with household characteristics. The interdependencies of life course trajectories together with resources produce role conflicts and daily dilemmas that are crucial for lone mothers’ employment opportunities and choices.