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Scholars have noted the “rise of the gig economy” (Freidman 2014), described as a surge in digital platform-based flexible work for independent contractors. Studies offer mixed reports on whether this entrepreneurial-style work has benefitted or detracted from contemporary workers’ economic security. However, scholarly conversations often neglect that at-will and highly flexible work already has a long, continuous history among middle class women, particularly mothers with children in the home, in the form of multi-level marketing. Multi-level marketing companies (MLM), a $36 billion industry in the U.S. (Keep and VanderNat 2014), involve approximately 20 million U.S. “consultants”—about 15 million of which are women between 25-45—where an individual typically pays a company for the opportunity to be a licensed distributor of the organizations’ consumer goods, often health and beauty products. How do women fare in this segment of the gig economy? This paper uses 54 in-depth interviews in a panel design, interviewing 30 women within three months of joining one of three focal MLMs, and then again around their one-year anniversary of joining the MLM. I find that while women prioritize gig economy features of flexible place and hours worked, they anticipate stable future earnings that are more commonly found in the formal economy of $4,738.28 per month, or approximately $56,000 annually. Women who joined companies with low start-up costs earned an average of $1.71 per hour, while women who joined an MLM with an average of $6,898 in expenses earned $10.36 per hour. While those that remained in the organization earned more money over time (an average of $12.22 hourly), one-third of respondents left their organizations due to unmet income expectations, especially relative to the work required. These findings highlight the financial vulnerabilities of women, particularly young mothers, who seek work opportunities “on the side” to complement their primary caregiving responsibilities.