Freelance work and other non-permanent employment arrangements are becoming increasingly popular ways for people to earn a living. Although these non-traditional activities offer novel, flexible ways to earn income from diverse sources, they also introduce nuanced recordkeeping, reporting, and attestation issues. We investigate characteristics of the gig economy, employee-versus-contractor considerations, bookkeeping, regulatory compliance, and external reporting considerations. We also explore best practices for CPAs who fulfill the role of trusted advisor for gig economy clients.