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The purpose of this study was to examine the challenges semi-professional VFL footballers experienced managing a dual career and the factors in the club environment that facilitated and impeded their dual career development.A case study of a semi-professional Australian Rules Football Club competing in the VFL (an elite second-tier Australian Football competition).Data collected over a three-month period comprised interviews, participant observations, and casual conversations with players and staff. A non-linear process of description, analysis, and interpretation framed the analysis, which focussed on the interaction between personal and environmental variables related to the management of footballers' career development.Time management, the demanding nature of non-athletic occupations and inconsistent training schedules were the most common challenges faced by footballers when combining their athletic careers with their non-athletic employment and/or educational/vocational pathway. The ability to negotiate flexible arrangements with the football club, and opportunities for mentoring by senior players were identified as facilitating factors that needed to be developed.Analysis of the findings suggests that in addition to the development of personal skills such as time management, developing an approach to dual career development that is: player driven; uses existing sources for mentorship and support and; recognises the specific challenges facing semi-professional footballers and their portfolios of work has the potential to support athletes in the development of their dual careers. Such an approach has the potential to attenuate the financial and logistical barriers to providing athlete support that can be observed in semi-professional sports.Time management and non-athletic demands were challenges to ‘semi-pro’ dual careers.Inconsistent training schedules were barriers to semi-professional dual careers.Flexible arrangements in meeting training demands important to dual careers.Utilising and formalising player to player mentoring could facilitate dual careers.