Purpose: To determine working distance, pupil diameter and illumination in real life conditions in a sample of presbyopic participants performing habitual tasks. Methods: A total of 59 presbyopic subjects (aged between 45 and 63 years) with different occupational backgrounds participated in the study. Participants were first interviewed regarding their habitual tasks with the aid of an ad hoc questionnaire, following which in-office photopic and mesopic pupil diameter was determined. Pupil diameter was also evaluated while participants conducted each of the self-reported habitual tasks by taking a photograph, which was later submitted to image analysis. In addition, working distance was determined with a measuring tape and the illumination that reached the pupil during each of the different tasks was measured, in lux, with a light meter. Results: The four most common habitual tasks were computer use, reading, sewing and sports. A high intersubject variability was found in pupil diameter, working distance and illumination conditions while conducting the same task. Statistically significant differences were found between the in-office measured photopic and mesopic pupil diameters and those obtained while participants were conducting their habitual tasks in real life conditions (all p < 0.001). Conclusions: Potential multifocal contact lens users may present with different ages, different jobs or hobbies and different preferences regarding lighting conditions and working distances. This results in different pupil size, even within the same task. This information may be critical when selecting a particular lens design and add power. Eye care practitioners are therefore advised to assess pupil diameter in real life conditions.