This paper uses the cultural preparedness approach to analyse the interface between the aspirations of immigrants and their engagement with systems of the host country. It draws upon interviews with 84 immigrants from 35 developing countries living in 9 high-income countries. Based upon Edmund Husserl's hermeneutical phenomenology, two studies are presented to understand the disturbance of equilibrium in cultural preparation status experienced by immigrants as they try to find their way in a host country. Aspiration-Engagement themes and responses to the challenges of integration are discussed. A model of aspiration and engagement based on the cultural preparedness approach is proposed as a framework that guidance and counselling workers could use to help immigrants optimise their engagement with the systems of the host country.