Negotiating a Second Remote 1099 Role for Overemployment

Published on 10/14/2025 Hiring & Talent Acquisition Insights

This individual has a clear opportunity to secure a second, remote 1099 contract job, leveraging the concept of 'overemployment' to significantly boost their income. The role involves client acquisition/retention and product improvement suggestions for a small tech solutions company. When negotiating, they should focus on defining clear project-based deliverables and milestones rather than hourly rates, given the company's preference. It's crucial to clarify expectations regarding time commitment and communication, especially since they have a full-time W2 job. They must also factor in the 25% self-employment tax (or higher) and the absence of benefits. This role offers diverse experience in a tech setting and substantial potential for additional income, even with a conservative estimate.