An 8 Year Bad Relationship with TurboTax
Feb. 15th, 2021 08:11 pm![[personal profile]](https://www.dreamwidth.org/img/silk/identity/user.png)
When I started filling out my income tax forms yesterday (yes, on Valentine's Day), TurboTax welcomed me back. "You've been using TurboTax for 8 years!" the tax prep software told me. Knowing that TurboTax's business model is to convince people they need its service because they can't handle taxes without it, I took the boast of 8 years not as a sign of deep friendship but as them gloating about how they've got me now.

Yeah, our relationship has been abusive.
My first date with TT was longer ago than 8 years, actually. I got partway through using it sometime in the late 00s when it choked on a special circumstance related to a Health Savings Account. I dumped it and kept filing taxes by hand.
I returned to TT in 2013 when filing my taxes got substantially more complex. New types of income I earned and changes in the tax code tripled the amount of paperwork required. TT automated the grunt work but wasn't helpful at helping me understand the rules, which is part of what I was looking for.
Over the years since then I've stuck with TT but had to keep a watchful eye on how it handles my finances. For example, in 2015 it almost cost me an extra $1,000 by inexplicably duplicating a stock sale. Pretty much every year since then it's made small mistakes in figuring my taxes— mistakes that would cost me several hundred dollars each year if I weren't checking its math so carefully.
Thankfully I do understand my own taxes. I could file them by hand if I wanted to. TT is such a help at automating the laborious work, though, it's worth sticking around in this broken-trust relationship. And hey, this year TT didn't make a mistake that would cause me to overpay my taxes by $300, $500, or $1,000. That improves its record to 1-8!

Yeah, our relationship has been abusive.
My first date with TT was longer ago than 8 years, actually. I got partway through using it sometime in the late 00s when it choked on a special circumstance related to a Health Savings Account. I dumped it and kept filing taxes by hand.
I returned to TT in 2013 when filing my taxes got substantially more complex. New types of income I earned and changes in the tax code tripled the amount of paperwork required. TT automated the grunt work but wasn't helpful at helping me understand the rules, which is part of what I was looking for.
Over the years since then I've stuck with TT but had to keep a watchful eye on how it handles my finances. For example, in 2015 it almost cost me an extra $1,000 by inexplicably duplicating a stock sale. Pretty much every year since then it's made small mistakes in figuring my taxes— mistakes that would cost me several hundred dollars each year if I weren't checking its math so carefully.
Thankfully I do understand my own taxes. I could file them by hand if I wanted to. TT is such a help at automating the laborious work, though, it's worth sticking around in this broken-trust relationship. And hey, this year TT didn't make a mistake that would cause me to overpay my taxes by $300, $500, or $1,000. That improves its record to 1-8!