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Changes in employment relationships have diminished the degree to which internal labor markets shape careers. Using comparative field studies, we examine how contract workers try to achieve career progression without the benefit of organizational guidance. Specifically, we examine how contract workers manage the career progression paradox: the problem of finding a job without prior experience. “Stretchwork” bridging from proven competencies to new ones helps reconcile this paradox. We identify four tactics used to acquire stretchwork, explore the conditions affecting the success of those tactics, and offer theoretical implications for career progression in external labor markets.