Look, I love a good complicated system. I believe in the concept of taxes for the public good, and I genuinely have fun filing ours each year--we always get a refund, so to me, it's a game to see how many points I can win, and the fact that the points translate into money just makes it that much better!

But that's largely because I use a well-designed tax software with a user interface that bypasses any direct reading of the bullshit federal forms and instructions. Last night, I had to delve into the real thing, and it was both infuriating and harrowing to a degree that surprised even me. The triggering sitch is that for the first time this year, I have to file the brand new (technically not brand new, but revived for the first time in decades) form 1099-NEC, not for myself, but for the podcast hosts that I "pay" out of the group funds that are delivered to me by Damn Interesting. Damn Interesting is sending me a 1099-NEC that includes that money as if it were all my income, so I have to deduct it as a contractor expense to them, or else pay taxes on all of it. If it were under $600 each, I could just say "yeah, I spent this money" and be done with it, but since it's more, I need to mail them each their own 1099-NEC, as well as file a copy of each co-host's form with the IRS.

Now, I could pay out the ass for business accounting software that would do that for me. But only the most expensive software--we're talking $300-$400 per year for an income source that barely exceeds that--will actually e-file the form for you. The rest just spit out a downloadable file in the proprietary IRS format, that you then must upload yourself via the government's FIRE system.

And how does one upload to the FIRE system? Why, it's easy! First, you have to file form 4419 (should have filed it last November, if we're being picky, and it goes without saying that it can't be e-filed because that's the whole point) and wait 45 business days for approval to use the system. To signify this approval, they will then send you a five-letter confirmation code. Then you need to create an account on the FIRE system website, with a username that is neither your email address, nor your five-letter code. For that username you must create a password, AND a "Secret Phrase," AND a 10-digit numerical PIN, all three of which will be needed to log in, every time. And just for funzies, the "secret phrase" maxes out at 20 characters and must contain numbers, letters, and special characters, so the use of the word "phrase" here is pretty disingenuous. It's just two damn passwords, plus did I mention the 10-digit numerical PIN on top of that??

But then, you might think, you could enter your three passwords, plus your five-letter confirmation code, and be allowed to upload your obscurely-formatted file. But oh, no. The five-letter confirmation code just sets you up to receive a TIN, which is another identifying number that I can't even remember what it stands for. First you login to your newly-created three-password account, then you enter your special 45-day-old five-letter code into the long digital form that lets you apply for a TIN... and then just as you get to the bottom of the TIN application, you are notified you are not eligible to do any of this without an Employer Identification Number, which as a sole proprietor is usually just your Social Security Number, but in this case that doesn't count, only an EIN will do.

Would you like to apply for an EIN?