In 1996, Nippert-Eng defined segmentation and integration as opposite while introducing the segmentation-integration continuum in the work- life research. This view affected largely how the relationships between work and non-work have so far been addressed in organisations. On the one side HR policies may favour ”segmentation” between work and non-work and on the side policies may favour ”integration”. Looking at the development of HR policies, it becomes evident that the industrial time favoured the first and that post-industrialisation favoured the second. Nowadays however HR policies combined with the organisational as well as societal discourses jeopardise this simplistic-two-alternative view. On the one hand, general media, political discourse but also in several research (see; Kossek, 2003, Wilson, et al. , 2004; Kylin, 2008) insist on the necessity for employees to ”find” energy while leaving their work behind and not be always in ”work” mode. On the other hand, organisations create flexibility and used IT devices so that work concretely becomes portable (Valcour & Hunter, 2010) and so that “working from home” becomes one organisational norm. The Shakespearian question is thus “to integrate or to segment” and the answer may be for individual: “how do I know, I get both signals”. As a matter of fact, the quality of work/non-work management and its consequences for individual’s well-being is depends foremost on individuals’ perception and interpretation of their contexts. Contexts matter as underlined by Kossek and Lambert (2006), Poelmans (2005), Ollier-Malaterre (2009) as well Languilaire (2009). Three levels of context are generally described in the work-life literature. First, the individual context, where individual’s characteristics as well as family and personal contexts are discussed. Research on the "couple" is an illustration of the individual context research (see Denker & Dougherty, 2013). Second, the organisational context, where the roles of organisational policy and culture are in focused (Ollier-Malaterre, 2009). Third, the societal context where the role of national (den Dulk et al., 2013) as well as international context are discussed (see Poelmans 2005). Hence a fit between the individuals’ work/non-work preferences for segmentation or integration and their individual, organisational and societal contexts should ease boundary management. In work-life domains, this refers to the person-environment fit framework (see Edwards & Rothbard, 1999) where a fit should result in a higher degree of satisfaction and well-being. For Edwards and Rothbard (1999), Kossek et al. (1999), Desrochers and Sargent (2003) a misfit implies that individuals are dissatisfied and are perpetually searching for ways to make things better. Such ongoing quest process can be stressful and thus have negative effects on individual’s wellbeing. As today’s working life de facto is composed of a ”dual” work-life discourse at diverse levels, individuals’ understanding and sense-making is central for their well-being This paper ought thus to discuss how individuals are coping with the complexity and duality of the “work-life discourse” that is de facto part of working life.