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The Book Nerd’s Guide to Important Tax Questions

Welcome to the Book Nerd’s Guide to Life! Every other week, we convene in this safe place to discuss the unique challenges of life for people whose noses are always wedged in books. For past guides, click here.
Once a year, I swerve abruptly from Team Harry/Hermione territory (yeah, I’ve shipped it all along) to plant my feet firmly in the Team Vernon Dursley camp. What time of year might that be? February, the first week of which is devoted to an onslaught from the post office. Is my mailbox full of letters from old friends or long-lost family, you ask? Has my pen pal been busy? Is it all a bunch of coupons? No, no, and no.
Between late January and early February, my mail is almost exclusively W2s, 1099s, 1098-Ts, CBGBs, 007s, 867-5309s, and other assorted tax documents. I might be exaggerating, but the mind is an organ easily fooled and prone to inflation. Regardless, the overall impression is one of a deluge of important, confusing tax documents that will bring down on me the wrath of the Internal Revenue Service if I so much as fold them the wrong way.
Perhaps these papers end up collecting dust on my kitchen table for a couple months because they don’t employ my brand of parlance. They distill my year into a set of numbers, which almost always seem to indicate a much higher income than I recall earning, quite frankly. The only time I really consider my income is when calculating how much of it goes to rent and how much of it is left to line the pockets of the nearest kindly bookseller.
I calculate the value of my year by how many pieces of prose I managed to cram down my figurative gullet. I calculate the value of my year by noting how many of my book club members haven’t gone screaming into the night. I calculate the value of my year by how many fewer square feet I have accessible in my living space.
I can only assume I’m not alone in this. Given that assumption, I’ve taken the time—while avoiding my tax return—to curate this brief list of FAQs for other book nerds besieged by this barrage of required paperwork. (Disclaimer: I am not an accountant.)
Does my Little Free Library count as a nonprofit or charitable organization?
Probably not, though I suspect there is an argument to be made that you are indeed providing relief to the distressed or underprivileged, speaking purely in a literary sense.
OK. Break it to me. What else doesn’t count as a charitable deduction?
The copy of Beloved you loaned to a friend that has now been out of your possession so long it qualifies as a donation. The two bucks you gave to your niece when she made you a macaroni bookmark. Also, the countless volunteer hours you’ve spent outside of work explaining the intricacies of the plot divergence between Game of Thrones and the A Song of Ice and Fire series.
Sorry.
Do my book recommendations qualify as a consulting business?
Do you mean to tell me your loved ones paying you for foisting books on them? Forget this. Run for president.
Do I have to send all this in? I was using this W-2 as a bookmark.
Life is pain, highness. Pay $2 to your niece.