This chapter outlines four specific challenges that graduates of higher education face as they transition from school to work in the new millennium: (1) The myth of a linear connection between studies and career options; (2) the purported gap between the skills and knowledge learned in school and the skills and knowledge needed in the workplace; (3) the challenge of preparing for multiple careers over a lifetime; (4) the need for lifelong learning. Learning how to transfer skills and knowledge across multiple contexts, and the ability for effective self-direction, are proposed as two important ways that job seekers themselves can effectively respond to these challenges. Higher education institutions are challenged to explicitly incorporate more reflection and other metacognitive practices into their curricula. They are also challenged to provide many (and varied) opportunities for students to transfer what they know and can do across multiple contexts, both in and outside of the classroom. Learners are encouraged to engage in greater self-direction of their academic and career trajectories and more fully understand how to create and find work by mobilizing their transferable skills in a variety of contexts, beyond those that are traditionally affiliated with their studies.

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