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The Box that Wouldn’t Check
Much ado about taxes, tech trouble, and kindness
Every year, for the past twelve, I’ve filed our taxes myself. It saves money, gives me a clearer sense of our finances, and — though I rarely say it aloud — gives me a quiet sense of accomplishment. I like knowing I can do it. That I’ve learned the system well enough to find my way through it. I’ve been using the same online tax prep platform for years. It’s familiar. I know where things are, and if something weird comes up, which it usually does, they’ve got folks who can help sort it out.
This year, when I logged in, it estimated I’d be done in two hours.
I had to laugh.
Most years, it takes me four, sometimes six hours. Still, I sat down with a cup of coffee, hopeful.
The income section was mostly fine. No surprises. The same sources we always report. I itemized our deductions. For a moment, I thought we were in good shape this year.
The platform showed we were due a refund. It would be a few thousand dollars between federal and state.
Woo hoo.
But the moment didn’t last.
Little errors began to pop up. Things I hadn’t expected. I found myself reaching out to the support team — first once, then daily — for help…
