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Crowdwork platforms like Amazon Mechanical Turk (AMT) fall short in supporting crowdworkers’ ability to reskill and transition jobs, even when these are valued by the workers themselves. To better understand how crowdwork platforms might address this need, we study how people change careers outside the context of crowdwork, and compare the resources they lean on to what is or is not available in crowdwork environments. We found that close interpersonal relationships, many of which formed out of collaborative projectbased work, were instrumental to successfully learning new skills and landing jobs. Building on these insights, we ideate on two potential workplace organizational structures for fostering relationships in crowdwork: an online environment that emulates the learning benefits of shared physical spaces, and a platform that organizes shared physical interaction around projects that support local communities.