A measure that could shape the future of the gig economy is on the California ballot. Proposition 22 would allow app-based transportation and delivery companies such as Uber, Lyft and Instacart,to classify drivers as contractors. A no vote would mean companies would have to treat drivers as employees with minimum wages and benefits such as sick time, unemployment insurance, and healthcare as required by California state law. Gig workers are divided over the choice between flexibility and stability. Companies supporting Prop 22 have contributed close to $185 million dollars, helping make it the most expensive ballot proposition in California history. We examine both sides of the debate.