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You Can Hate the IRS and Still Want it to Work

February 9, 2026 by Bill Bourbonnais

If you ever needed proof the IRS is held together with duct tape and caffeine, here it is. From a recent article in Government Executive magazine: “The Internal Revenue Service is asking seasoned employees without any direct tax experience to perform entry-level tasks of answering phones and processing tax returns, a step impacted staff call unprecedented as the agency scrambles to prepare for filing season.” These include employees from departments like human resources and IT, which means people who normally reset passwords and process onboarding paperwork will be untangling the tax code.

Filed Under: IRS, taxes Tagged With: Audit Risk, Business Owners, IRS Delays, small business taxes, tax compliance, tax planning, Tax Smart, tax strategy

The Weirdest Tax Deductions That Actually Worked (No, Your Dog Is Still Not One of Them)

January 13, 2026 by Bill Bourbonnais

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.”

Filed Under: IRS, taxes Tagged With: business deductions, CPA humor, entrepreneur finance, financial strategy, IRS approved, small business taxes, tax deductions, tax planning, tax strategy, tax tips

A Charlie Brown Tax-Giving

November 25, 2025 by Bill Bourbonnais

For most families, Thanksgiving means gathering around a perfectly roasted turkey, sharing gratitude, and trying to avoid discussing politics or crypto. But in A Charlie Brown Thanksgiving, things are a little more “improvised.” Instead of turkey and stuffing, the Peanuts gang ends up with toast, popcorn, pretzel sticks, and a side of existential confusion. And honestly? That makes it a pretty realistic holiday picture. Because whether you’re cooking a turkey or prepping a tax plan, life serves up whatever’s in the pantry. Charlie Brown’s holiday feast is basically a metaphor for the final weeks of tax-planning season. It’s messy, it’s chaotic, and half the participants assume someone else is doing the hard work. If that isn’t December tax planning, I don’t know what is.

Filed Under: Uncategorized Tagged With: business tax tips, December deductions, financial planning, IRS deadlines, last-minute taxes, small business tax, tax, tax planning, tax pro life, tax reduction, tax savings, tax strategy, taxes, year-end strategy

Bone to Pick: Travelers Howl Over Italy’s Dog Tax

November 12, 2025 by Bill Bourbonnais

If you ever thought vacationing with your dog was a walk in the park, Italy just tossed a new stick into the game. The Province of Bolzano in northern Italy is planning to charge visitors about €1.50 per day, or roughly two bucks, for the privilege of bringing along their pup. That’s right: tourists are choking on a brand-new “dog tax.” Sit. Stay. Pay.

Filed Under: taxes Tagged With: BolzanoNews, DogFriendlyTravel, FurBabiesAbroad, ItalyDogTax, PetTravelTips, tax, tax strategy, TaxHumor, taxpolicy, TouristFees, TravelTaxes

Labor Takes a Holiday. Capital Gets the Breaks.

August 26, 2025 by Bill Bourbonnais

Every September, Americans fire up their grills, crack open a cold one, and celebrate Labor Day. But it didn’t start as an excuse to party, or buy mattresses at 30% off. It was born in the late 1800s, when workers sweated 12-hour days just to keep food on the table. Strikes turned bloody — most famously in Chicago at the Haymarket Riot — and demands for fair pay, safe conditions, and reasonable hours grew too loud to ignore.

Filed Under: Retirement, taxes Tagged With: business tax tips, capital vs labor, financial planning, labor day truth, passive income, real estate tax breaks, smart money moves, tax planning, tax strategy, wage tax burden

The Devil’s in the Deductions-Digging Into the “Big Beautiful Bill”

July 8, 2025 by Bill Bourbonnais

You already know the highlights: the Big Beautiful Bill (BBB) is Congress’s latest effort to stuff 10 pounds of tax cuts into a five-pound bag. It locks in most of the 2017 Tax Cuts and Jobs Act. Marginal rates stay low. The standard deduction stays chunky. The qualified business income deduction lives to fight another day. Cue the confetti (and another round of Roth conversions while you’re at it).

Filed Under: taxes, TCJA Tagged With: 2025 tax law, Big Beautiful Bill, capital gains, gambling deductions, IRS, passive income, professional gambler, QSBS, startup taxes, Tax Cuts and Jobs Act, tax reform, tax savings, tax strategy, taxpolicy, taxrelief

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