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PurposeThe purpose of this paper is to scrutinize the transition from university to working life through different theoretical approaches. Inspired by Barnett the paper also asks: What is it to learn for an unknown future? According to Bartlett neither knowledge nor skills are sufficient to enable success in the contemporary world. What is needed are certain kinds of human qualities and dispositions. The paper seeks to introduce two examples that help us to analyse the phenomenon from the perspectives of higher education and working life.Design/methodology/approachThe data consists of an interview on pedagogical practices in actor training and of group mentoring discussions in a teacher community.FindingsBased on the observations, the educational process itself with its disturbing factors, the transition to working life, and finding one's place in it are all sites that provide their own challenges for an unknown future. The contradiction between security and the unknown inscribed in them produces uncertainty. Furthermore, the paper maintains that self‐challenge is one of the dispositions needed for living with uncertainty.Originality/valueDialogic mentoring is a tool by which the problems and contradictions raised by daily practices can be challenged. Some of these contradictions may have their roots in unsolved challenges during education, and then have to be shouldered by the work community. The concept of dialogic mentoring is a fruitful pedagogical tool in preventing and reducing work‐based stress and exhaustion experienced by newcomers in work communities.

The article presents practices of distributed pedagogical leadership and generative dialogue as a tool with which management and personnel can better operate in the increasingly turbulent world of education. Distributed pedagogical leadership includes common characteristics of a professional learning community when the educational actors intentionally share a common mission. There, all stakeholders take collective responsibility for students' learning. Generative dialogue is a way to negotiate in this realm in generating new knowledge and understanding. To introduce this process in practice, the article describes two Finnish learning environments where the stakeholders define, first, the critical nodes, paths and contents in students' individual learning paths in vocational education, and, second, presents examples of generative dialogue within distributed pedagogical leadership.

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