Comment by BrandonM | Hacker News Reader

Comment by BrandonM | Hacker News Reader

For anyone who can program (including spreadsheets!), it's not all that hard to file your own taxes the old-fashioned way. To do it digitally, just use https://www.freefilefillableforms.com/ and start with a 1040. Read each line carefully and go from there.

The IRS has tons of great resources, and you can even call them up. Each form has a companion instruction booklet (online PDF), and sometimes those instructions refer to an IRS publication with additional clarification. If you can read a technical blog post and follow a clear procedure, you can file your own taxes.

I've been filing taxes the (new) old-fashioned way for my wife and I for the last 3 years. That includes 330+ days abroad (Federal Earned Income Exclusion), a sole proprietorship, an LLC, an ISO exercise (AMT), 3 separate states, and 5 separate cities.

Each time, it has taken me a full 12-16 hours (a solid day or two on a weekend) for federal, multiple states, and multiple cities. It's not the most fun, but by the end of it, I understand our taxes and finances a lot better. We can arrange our situation better going forward. We can keep more appropriate records to make the next year's filings easier. And most of all, I have the satisfaction of not funding an industry that lobbies against my interests.

> it's not all that hard to file your own taxes the old-fashioned way

> Each time, it has taken me a full 12-16 hours

You have a strange definition of "not that hard".

This is exactly my experience trying to do it the old fashioned way. The IRS's documentation is written in accountant speak so deciphering what each means is an effort and all of the time it takes adds up. Who else uses the word "schedule" to mean "form"? And then there are so many places where it talks about "qualifying" this or that without telling you how you know if something qualifies.

And that's before you get to the nightmare if you own stocks. My wife inherited some telecom stocks from her grandmother. Her grandmother got them as part of her paycheck when she worked at AT&T. Unfortunately she didn't keep any of the original documentation for them (my wife had to track down the stock management companies and get them to reprint the certificates). These stocks were then of course split across all of the baby bells and merged and split a ton of different ways over the years. Then one of the companies merges and we get a payout for a fractional amount of a share and have to calculate the strike price of the stock for the sale.

As an average person this seems like an impossible task. We just enter 0 and pay a ton of extra tax because how in the hell are we supposed to do that calculation? As far as I can tell we can never sell these stocks.

> You have a strange definition of "not that hard".

That's fair, but by-far the hardest thing about filing taxes for us has been prorating our income based on how long we lived in each part-year municipality. Adding to that, some cities/states give you a credit on the taxes, some deduct from the income, and yet others multiply by the number of business days you were a resident. If it was just a matter of filing a 1040, itemizing deductions, and transferring that same info to state/city taxes, it would probably take me 3-4 hours.

I agree that your situation sounds difficult, but I doubt that TurboTax is really making that easier. You likely need to seek out a true tax preparer/accountant. My comment was specifically targeted at those who are using DIY online software... It's just honestly not that much harder to use forms. (I could have been clearer about who my comment applied to.)

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