Jennifer. J. Chow

Top Ten #TaxFails

Even though I know that taxes (and death) are certain, I feel like I’m always ill-prepared. And this year seemed to be full of mishaps. So, without further ado, here’s my Top Ten List of personal #taxfails this season:

10) Procrastinated. Despite having the date automatically labeled in my calendar, my sense of time got muddled around March. Then, all of a sudden, I discovered it was early April and started to panic…

9)  Didn’t organize. Sure, I kept all my receipts. But the fact that they were tossed willy-nilly into a box wasn’t quite as helpful as I’d envisioned.

8) Skipped the in-box. I was great at checking physical mail. But I needed to remind myself to check email as well for important docs.

7) Didn’t verify entries. I’ve got this lovely spreadsheet for writing expenses. I definitely added entries, but at the very end, I still needed to double-check the data (things got missed, double-added, or categorized incorrectly).

6) Forgot about mileage. Since I get to do deductions for my writing business, I need to keep track of mileage. Often I’m spent after driving to different events and fail to log in miles. Thus, I had to go back to my calendar and through all my outings and use maps to calculate everything.

5) Excluded expenses. When I go shopping, sometimes I think of things as household expenses. But how about printer paper? Oops. (Honestly, that’s mostly me because kids these days turn stuff in online.) I needed to add those kinds of expenses to my cost of doing business.  

4) Forgot passwords. Why is it that when I check accounts during tax time, I forget the password? I had to re-verify my identity in a few instances to get back into the portal.

3) Didn’t count the books. Yep, I’ve got inventory. And now that I’ve bought back books (☹ about dying mass market paperbacks), I needed to actually count and keep track of them.

2) Failed to eat. Okay, not technically true. But I found that prepping for taxes takes a lot longer than predicted, so I needed to fuel up on snacks, drinks, patience…

1) Got TurboTax—sorta. And only the TurboTax box. So I went to Costco and got the usual software only to find that I’d purchased the shell—literally, it was only a mock box with no download codes inside. I had to slink back to Costco, receipt in hand, to get the actual item (which by the way comes in a very similar-looking box).

How did tax season go for you?

34 thoughts on “Top Ten #TaxFails”

  2. With everything going on this year. I was disorganized. Yes, you read that right. Me! Disorganized about taxes! Here’s my top 10.

    10 – work travel got in the way at the wrong time for organization

    9 – moving offices at the same time, causing more disorganization

    8 – stock mergers messing with the portfolio details

    7 – looking for my TurboTax account info from last year

    6 – I had to look for all documentation because I don’t have an envelope or a box I keep everything in. Smart move Jenn

    5 – what did I spend to publish my book last year, legal fees, professional services, swag (don’t even remember if I added that), etc.

    4 – supplies I can or can’t deduct because they aren’t exclusively for writing. various softwares are a no. And malice, I can deduct the convention this year, but not the hotel cost, since I’m local.

    3 – scouring bank statements, trying to find payments I received from two different sources and printing them out.

    2 – dealing with daddy’s taxes as well, and having several appts with the Block to get his 2023 and 2024 returns amended

    1 – friends and family contacting me all the time with tax questions instead of trying to answer my own questions

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  3. I feel for you, Jen. Every year, I say I’m going to track my writing expenses and income (what’s that?) throughout the year. And every year, I fail to do so.

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  6. I’m really mad! I’m on the second year with a new accountant and he had to file an extension because he didn’t finish our taxes on time! I turned them in on March 9th! He had to do the same with Eliza’s. I’ve never had an extension in my life. He better guarantee it won’t happen again or I’ll be hunting for yet another accountant.

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    2. It’s so great to hear that an accountant doesn’t like doing their own taxes, either. I’ll have to remember that idea for my next Irish B&B Mystery (since my MC is a very organized accountant in a disorganized family business. I’m sure that wears her out.)

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  8. Thank goodness for Robin, who’s been doing my taxes (and hers, and my parents when they were still alive) for many years. She actually kind of enjoys it.

    Your Turbo-Tax story is hilarious (but a bummer for you, I know). And I don’t think I’ve ever in my life forgotten to eat….

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    1. Yay for Robin!

      Yeah, that TurboTax buying was an adventure. And I’ve never forgotten to eat an entire meal…though I have a few friends who when they get too busy need to be reminded to eat by their significant others.

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  9. This is annual ritual I could do without! I always mean to get super organized and track my expenses as I go, but so far that’s yet to happen! Congratulations, you’re good for another year! Or at least 11 months…

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  10. Jen, this was the best post (with best comments) because now I know I am not alone! (And also, the Top 10, ha/aargh!) I hate even looking at numbers, and even more the idea that, with all those writerly expenses, I am left with…sigh. Even though we have a saintly accountant, who always schedules us on the Sunday afternoon before Tax Day, I dread The Yearly Reckoning with a passion. I also hate spreadsheets, so they’re out. I went digital as much as possible this year, but…how many times does one have to double-verify one’s identity and passwords and codes? That was the worst!!! (Mostly b/c I doubt those steps do any good anyway. I imagined AI cackling in the background.)

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  11. Mock box?!!! Oh my gosh, that is so unfair of the store to put that out there for unsuspecting shoppers. I’m sorry, Jen.

    But thank you for this–a relatable reminder of how hard it can be to put together the submissions.

    I hope all is well now (and your muffins look delicious).

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