Quickbooks & Small Businesses


For the record, when it comes to Quickbooks, I think I’m cursed. Every time I have to upgrade, it’s a nightmare. This is the part of being an indie author I don’t like: I am CEO, CFO, IT, marketing, everything. And keeping on top of my financial paperwork is a nuisance. It takes me hours every month to complete the paperwork and then when tax season rolls around, I spend even more time scrambling to make sure it’s all done and correct.

I have often considered paying someone to do my monthly financial paperwork, but I am capable so I can’t justify spending the money on it. And then something like this happens and I think “well maybe I should.” I have been using Quickbooks 2016 since 2016. In July it finally died because that’s what Quickbooks does every so many years and you have to upgrade to a new year. At the end of August, I upgraded to 2020. And now all my 2019 financial work has to be redone… while I’m struggling to get my other project done.

An extension had to be filed for our 2019 taxes. In 2017 my business address changed because we bought a house. I had to send in a form to the IRS… but shit happens. As a result, I did not get my Google 1099 in January. In March they were finally able to say “the address we have on file where we sent your 1099 is not the address you are giving me.” Uh what? Okay, so I will resend that form and wait for the IRS to take care of it… 6-8 weeks no problem, but it will probably be after April 15th before it gets done, so an extension until October was granted.

And then the pandemic happened and it was late July before Google and the IRS got their paperwork changed. and I got my 1099 for 2019. And by then, my Quickbooks wasn’t working…

What happened to my 2019 stuff with the upgrade? Good question, even Quickbooks can’t explain it or fix it. I sent them 3 different back-ups to convert to 2020 and spent an entire day chatting with tech support and still nothing. They can’t explain it, I can’t explain it. It even removed all the recurring transactions that had started in 2019 from my completed 2020 paperwork… but only the recurring transactions that began in 2019. I’ve had 2 recurring (Microsoft and Dropbox) for multiple years… They both stayed. But BookFunnel and Canva which both were started in 2019 disappeared completely from 2019 and 2020. It’s as if Quickbooks saw 2019 and went “nope, didn’t happen.”

However, in the decades I have been working with Quickbooks I have found weird shit happens to me with Quickbooks. Weird shit that even Quickbooks can’t explain or fix. Between 2006 and 2008 I worked as a bookkeeper for a non-profit. I completed the monthly report, printed it, saved it, backed it up and when it was opened later all the transactions had been reversed… All the outgoing payments were converted to deposits and vice versa. Quickbooks swore it was impossible… But I had the completed accurate reports printed that showed them correct and then there was the data that was incorrect. Which is why sometimes I wonder if I can afford to pay someone to do my Quickbooks work for me…

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