This paper presents reflections on an international field trip for Indigenous students enrolled in an Education degree at a university in Australia. The field trip was co-developed with staff, students, and community partners of a Canadian university, as a pilot project to prepare Indigenous students for work in various cultural contexts. This paper outlines considerations for planning and coordinating an international career development opportunity, from inception to completion. Successes and failures of the program are discussed, recognizing the pitfalls that plague many well-intentioned program developments. The paper then argues for an intentional and generative approach in co-developing and co-delivering international learning experiences. Finally, it offers reflections on the need for more explicit alignment between academic outcomes and career aspirations, supporting students to articulate knowledge and skills acquired to translate them into the world of work.