How does one file their taxes when working for Bossman?

Good question.

It was initially agreed upon that I would be paid as an independent contractor and therefore receive a 1099 form, not the traditional W-2. Although it's pretty much illegal since I'm a permanent employee and he just wants to avoid paying payroll taxes, I went ahead with the plan since I was really excited about the job when I first started. I think we all know by now that my sentiments have since changed...

This past Sunday, I went home with my file-a-fax full of receipts and bills I had saved over the course of my employ as an independent contractor, ready to write off business expenses to my heart's content. However, a small snag was reached when diligent TurboTax asked me to enter the information from box 3b of my 1099. Box 3b? I suddenly realized that I couldn't fulfill the request since I didn't have a 1099 form from my employer (Bossman) and therefore had no idea what would be in box 3b.

Keeping my cool, I dial up Bossman. The conversation (somewhat abbreviated) went as follows:

Faithful Assistant: "Hi Bossman, I'm sitting here trying to do my taxes and realized that I haven't received a 1099 form from you yet. Do you know when I should be expecting it?"
Bossman: (somewhat dreamily) "Um....No. I don't have any idea."

Awkward silence...

FA: "Oh. Ok. Umm..."
BM: "Well what goes into that?"
FA: (trying to hide frustration) "Well, you or your accountant are supposed to fill out a 1099 form and submit it to me and the IRS so I can report my earnings and file my taxes."
BM: "Oh."
FA: "Should I talk to your accountant about it?"
BM: "Well, why don't you just figure out the steps that go into it and we'll go from there?"
FA: "Ok. I guess I can do that but I'd really need to speak to an accountant to make sure it's all correct."
BM: "Well...if you can figure out what needs to go into that then we can work it out."
FA: (getting audibly more frustrated) "Alright. I do need to get this taken care of really soon since the deadline is coming up. Do you have an accountant that handles your taxes?"
BM: (Still dreamy, I now think he's watching tv while talking to me) "There is an accountant but I don't think he'd handle this kind of thing..."

Awkward silence #2...

FA: "Um. You also have to file a 1099 as a part of your taxes. Your accountant should know about this if he's filing for you."
BM: "(audibly reaching his limit for how long he feels like talking to me) Ok. If you can just look into what information you need, you and I can go from there on Monday."
FA: (awash in defeat) "Sounds good. I'll see you Monday."

endnote: He told me to take the day off on Monday.