The problem of resolving the conflict between professional and familial responsibilities—or more broadly, striking a balance between work and private life—has remained one of the most pressing concerns of labour law for an extended period. Due to rising female labour market participation, population aging, and changes in archetypal employment and family structures, work-life balance has gained prominence in public discourse—primarily affecting workers, with significant implications for employers and governments. Against this backdrop, the concept of work-life balance has evolved gradually within the EU, taking shape through both soft and hard law instruments. While it was once perceived—under the influence of prevailing cultural norms, reinforced by specific policies, measures, and even Court of Justice rulings—as a concern primarily affecting working mothers as default caregivers, it now encompasses working fathers as well as all workers providing personal care for dependent family members. Yet, despite decades of legislative progress, a persistent dilemma remains: Have reconciliation measures truly accomplished their aim of fostering substantive gender equality—not merely in employment, but also in the distribution of unpaid caregiving duties within households? Accordingly, the introductory section of this paper examines the broader societal context of work-life conflict, analyzing both the dissolution of the traditional ‘breadwinner/caregiver’ model and persistent barriers to gender equality in employment and caregiving distribution. The first section provides a brief overview of the EU legislative framework governing reconciliation of professional with family and private life, through three analytical prisms: regulatory approaches, feminist social theories, and equality models. The paper subsequently examines the 2019 EU Work-Life Balance Directive, assessing through a gender-critical lens both its novel provisions—such as paternity leave and carers’ leave—and preexisting measures such as parental leave and flexible working arrangements. Finally, it scrutinizes the current legal framework in North Macedonia, evaluating the extent to which the law of this EU candidate country is in conformity with the EU law on work-life balance.