Return to work remains a central issue for many traumatic brain injury (TBI) patients. The present literature generally ignores the complex work issues involved for high-functioning individuals, in whose hands may lie the fate of many other workers. This case discusses return-to-work challenges facing a 64-year-old high-technology company founder and president. Following a bicycling accident, he sustained intracerebral hemorrhage with an initial Glasgow Coma Scale of score 12. Although postmorbidly he still maintained a relatively high level of cognitive functioning, his case highlights special challenges during workplace rehabilitation of patients with cognitively demanding jobs, including (a) a higher potential for patient frustration given the gap between function and job expectations and (b) confidentiality issues regarding business employees and competitors. Rehabilitation health care providers can benefit from lessons learned here, including tapping into these patients' strong motivation for return to work, accessing the likely higher remaining cognitive level, and drawing upon the likely strong social and professional networks available. Finally, the importance of the role of stress-management techniques in order to cope with high frustration levels is highlighted.