Every tax season, Americans ask the same hopeful question: “Can I deduct that?” Sometimes the answer is “no, sorry.” Sometimes the answer is “absolutely not, please stop talking.” But every once in a while, the answer is: Shockingly . . . yes. Welcome to the wild side of the tax code, where deductions roam free, logic occasionally takes a lunch break, and the IRS reluctantly admits, “Fine. We’ll allow it.”
IRS
When “Fair Share” Sounds Like “Find the Exit”
Raising taxes on the rich is usually a party trick politicians pull out when they want applause, not when they actually plan to do it. Lately, though, some of them are dusting it off again, and high earners are reacting the same way people do when the waiter raises an eyebrow and says, “So . […]
Fetch is Not Going to Happen
This time of year, most tax pros are gearing up for yet another season preparing returns. But it looks like Tax Season 2026 might come with a new kind of tail-wagging drama. A New York attorney named Amanda Reynolds has taken a big bite out of the Internal Revenue Service, asking a federal court to […]
The Saddest Little Tax Plan on the Lot
Every December, A Charlie Brown Christmas shows up and reminds us that nothing has really changed since 1965. We’re still stressed. We’re still distracted. We still think the answer to our problems is buying one more shiny thing. (Maybe painted pink!) And we’re still weirdly confident that if we just try harder, this year will finally feel like Christmas.
Rounding Up and Cashing Out
Every so often, Uncle Sam announces something that makes taxpayers stop, blink, and ask, “Wait… we’re still doing that?” Now that conversation has landed squarely on the humble penny. Yes, the little copper-colored coin that costs more to make than it’s worth, that falls between couch cushions like it’s trying to escape the junk drawer, and that we all secretly wonder what to do with when we get it back as change. Last week, Treasury Secretary Scott Bessent personally minted the last five of their kind. And many Americans say this with love: it’s about time. You know inflation is bad when even money is worth less than the metal it’s made from.
When TikTok Becomes TaxTok
Buckle up, buttercups — it’s time to talk about the avalanche of advice flooding Instagram, Facebook, TikTok and beyond. You know the kind: “Just buy a short-term rental and poof — zero tax!” It’s catchy. It’s viral. And it’s mostly hype. Sure, short-term rentals can offer tax advantages, maybe even significant ones. But the idea that you […]