Retirement tax questions

He’s not issuing himself a W2. He’s receiving a W2 via the staffing company for work contracted through other businesses. The worksite business calculates his time, sends it to the staffing company, then the staffing company does the payroll taxes and sends out his income each week based on the number of hours he works. I should also clarify that each worksite is a different contract agreement between the staffing company and himself that they negotiate prior to work starting. I understand what you’re saying, but this is a bit different than your typical independent contracting, for say construction, where you find the work yourself, negotiate directly with the business you’re working at, and receive untaxed income directly from the worksite business and have to pay taxes at the end of the year. Now I work directly for a company at a single location, thus not making me an independent contractor even though I’m doing the same work. So I can’t be a sole proprietor under these circumstances.