This research aims to investigate how using time management apps with systematic breaks affects the focus and productivity of first-year students during self-studying. It specifically explores their experiences of taking breaks through a self-tracking timer app using the Pomodoro technique. The study also examines how the students’ phone habits impact their studies. A mixed-methods approach was employed, beginning with a questionnaire to understand the participants’ phone habits and time management app experience. They then used a Pomodoro app for a week, with the option to keep a diary. Finally, semi-structured interviews explored their experiences, and the qualitative data was analyzed inductively through a thematic analysis. Participants found mobile phone use distracting while studying and had difficulty reducing it. The Pomodoro app helped some focus and reduced phone use, but others preferred existing methods or started skipping breaks. Breaks spent online were common but offline breaks were generally valued higher. Participants emphasized achieving productivity as a path to well-being, staying on track, reducing stress, and leading to satisfaction. Regarding design implications and time management preferences, participants look for simple self-tracking methods like calendars, drawing an urge to more long-term planning tools rather than timers.