Profession-based freelancing platforms use algorithmic reputation systems to match labor supply and demand by signaling a worker’s competence through a platform-specific reputation. Freelancers new to a platform encounter the cold start problem; they lack platform-specific reputations and the interactions used by the platform’s algorithms to build one. Studies on workers who overcome the cold start problem assume they are motivated to gradually build platform-specific reputations because they have a committed and long-term orientation to their work. Yet, these assumptions overlook groups with other motivations and how they can be successful. Older workers are one of the fastest-growing demographics of freelancers, which research suggests violates the assumptions of long-term and committed orientation. Because it is unknown how older workers can successfully overcome the cold start problem, we conducted a qualitative study of older workers who transitioned from conventional employment to online freelancing through Upwork. We found that older workers realized that building platform-specific reputations required accepting jobs misaligned with their initial motivations for pursuing platform work. This misalignment was particularly pronounced for older workers tethered to their career occupations who often decided to stop using the platform. In contrast, those who persisted in building reputations were less tethered to their prior occupations. Ironically, as these occupationally untethered older workers established platform-specific reputations, they found that the platform funneled them into taking jobs related to the occupations they intended to leave behind. We elaborate on how this ironic dynamic occurs and its implications for theories of platform work and the aging workforce.