We explore the outsourcing strategies of freelancers in Online Labor Platforms. Prior literature has focused on how buyer attributes, freelancer attributes, and gig attributes can efficiently match freelancers and buyers. They have considered freelancers and buyers as two separate entities, where only buyers are considered as the firms who outsource labor. We analyze the buying activities and freelancing activities of the same freelancer in the online labor platform to explore their buying motivations. Our initial results show that freelancers develop outsourcing strategies for both core activities and peripheral activities to other freelancers. We conduct text analysis using NLP methods to analyze the text content of a freelancer’s buying and freelancing tasks to explore the strategies for outsourcing.