Background The benefits of mindfulness interventions are well‐known, but their challenges and individual differences in reactions to these challenges are much less clear. Methods The study used a mixed‐methods design to investigate the individual trajectories of daily experiences during meditation in a sample of novice volunteers participating in a 3‐week, distance‐based, guided meditation intervention (N = 175). Results Multilevel modelling revealed individual differences in the change trajectories of the experiences of effort, meaning, and boredom during meditation, indicating that meditation gradually became less effortful, less boring, more interesting, and more important over the 3 weeks. The individual differences in the levels of these experiences and their change trends were associated with baseline differences in well‐being, reflective processes, self‐management, and self‐control skills, as well as autonomous motivation to engage in the course. Conclusions Individuals who are initially more autonomous and mindful find it easier to engage with online mindfulness interventions and draw more benefits from the process, whereas those with lower self‐regulation skills or higher proneness to rumination are more likely to experience mindfulness as effortful and boring, and, eventually, to give it up.