A workshop at the 2008 ASPHO Annual Meeting functioned as the first step in a systematic needs assessment of the particular challenges to satisfaction and success in the middle and senior phases of career development for pediatric hematologist/oncologists (PHOs). The 61 ASPHO members who attended were randomly distributed to small discussion groups based on self-identified career stage. Groups completed challenge forms for each issue identified as pertinent to their own stage of professional development. A total of 71 forms with useable data were generated by the groups. The largest number of challenges described (26) clustered around themes of Work-Life Balance followed by Transition and Succession (18), Management and Finances (15), and Keeping up to Date (13). Mid-career groups were more likely to identify Work-Life Balance challenges while senior stage groups were more likely to articulate Succession and Management challenges. The article describes the demographics of the workshop participants, summarizes the content of challenge themes and the associated suggestions for management. It is hoped that this effort will assist educational and career planning efforts by individuals, institutions, and ASPHO as a professional society.