<prompt> Human: I know my boss does not pay personal taxes and constantly tries convince me to stop paying too. He talks about signing your name in all caps and really believes in all thats mumbo-jumbo.I work on contract and receive a 1099 he says I wont be receiving anything anymore and it will be up to me to report my earnings.I am worried this is going to bite me in the ass. I am meeting with a lawyer tomorrow, what are some questions should I be asking to not seem like an idiot?  <response>: My first question is what do you do? Obviously you are classified as a 1099. Do you believe you should be an employee? or are you actually a 1099?As a 1099 assuming you are legally one, your boss doesnt withhold any taxes. Further, he doesnt give a crap if you are an S-corp, llc, etc. You do 1000.00 worth of work, he pays you 1,000 bucks. At the end of the year, he sends you a 1099. Also, not sure why he is against sending you a 1099. Other than the labor to produce the form, it cost nothing. Plus if you are going to write off services performed by contractors, you should have the 1099s to balance.Anyway. If you are an employee the employer should be withholding taxes. It sounds like he has you listed as a 1099 probably illegally. If the IRS finds out, they will be giving him a phone call, I promise you that.First question. Should you be an employee, or 1099? Take this test if unsure. 2. How long have you been with them? How much have you made?3. Has any tax been withheld? If not, are you prepared for a large tax bill possibly 30-40 of what you made this year.---Here are your options as I see it. 1. Continue as an independent contractor. Even though your boss doesnt send a 1099, you can still pay your taxes. Downside is your boss is cheating the system, and you have to pay your bosses share of your FICA taxes. Not recommended. 2. File a form SS-8. This will get the IRS to classify you as an employee or independent contractor. File your taxes, you can fill out a form 8919 for uncollected FICA taxes once the IRS agrees that you are an employee. Now the IRS calls up your boss for that money, and not you. you will still owe quite a bit though. This only relieves you of your employers share of FICA taxes. Also note, if he has you listed as a 1099, he is probably not paying workers comp or unemployment insurance, so if you were injured or fired, you would not be eligible for either program.3. Look for another job. Probably a great idea anyway. Once you have the new job, go for option 2, so you are not on the hook for so much.I would make sure to bring him your paycheck stubs. Ask him about withholding, a quick very rough estimate of what you will owe in taxes so you can start saving if needed and what else to do. If you have not paid any taxes this year, it could be wise to make a quarterly payment and avoid penalties for not paying taxes throughout the year. 