Non-professional runners make extensive use of consumer-available wearable devices and smartphone apps to monitor training sessions, health, and physical performance. Despite the popularity of these products, they usually neglect subjective factors, such as psychosocial stress, unexpected daily physical (in)activity, sleep quality perception, and/or previous injuries. Consequently, the implementation of these products may lead to underperformance, reduced motivation, and running-related injuries. This paper investigates how the integration of subjective training, off-training, and contextual factors from a 24/7 perspective might lead to better individual screening and health protection methods for recreational runners. Using an online-based Ecological Momentary Assessment survey, a seven-day cohort study was conducted. Twenty participants answered daily surveys three times a day regarding subjective off-training and contextual data; e.g., health, sleep, stress, training, environment, physiology, and lifestyle factors. The results show that daily habits of people are unstructured, unlikely predictable, and influenced by factors, such as the demands of work, social life, leisure time, or sleep. By merging these factors with sensor-based data, running-related systems would be able to better assess the individual workload of recreational runners and support them to reduce their risk of suffering from running-related injuries