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Retirement

The Saddest Little Tax Plan on the Lot

December 17, 2025 by Bill Bourbonnais

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.

Filed Under: IRS, Limited Liability Company, Retirement, taxes Tagged With: avoid the audit, business strategy, Charlie Brown, December deductions, real talk taxes, small business finance, tax planning, tax season, tax smart moves, year-end taxes

Guy Math: The Drill That Keeps on Giving

September 16, 2025 by Bill Bourbonnais

By now you’ve probably heard of “girl math.” That’s the playful financial logic that turns a return into a profit or makes anything bought with cash “basically free.” Pay for Taylor Swift tickets six months in advance? By the time the concert rolls around, they cost nothing. It’s not necessarily “wrong” math. It’s “emotional” math. It explains how money feels rather than how it flows. Accountants everywhere faint when they hear it, but they faint quietly — back into their spreadsheets where they feel comfortable.

Filed Under: IRS, Retirement, taxes Tagged With: businesstaxes, DIYFinance, EntrepreneurLife, FinancialHumor, GuyMath, IRSReality, SmallBusinessTips, TaxDeductions, TaxSmart, TaxStrategy, WriteOffWisdom

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

Transition Planning

May 29, 2025 by Bill Bourbonnais

Retirement Deserves a Strategy, Not a Guess Life rarely follows a straight path. It’s full of transitions—some expected, others surprising. Career changes, marriage, divorce, inheritance, the birth of a child, or the passing of a loved one—each event has the power to reshape your financial picture in significant ways. Among these transitions, retirement is arguably […]

Filed Under: Retirement Tagged With: RetirementPlanning, RetirementStrategy, RetireSmarter

Retirement Income Security

May 15, 2025 by Bill Bourbonnais

Why Smart Planning Matters Now More Than Ever

The past few years have been a whirlwind for retirees and investors. After nearly two decades of low inflation and relatively calm markets, the post-pandemic world has brought economic surprises that few saw coming: surging inflation, sharp interest rate hikes, and significant market volatility.

Filed Under: Retirement Tagged With: FinancialLiteracy, IncomeStrategy, InflationProtection, MarketVolatility, RetirementPlanning, SmartMoneyMoves

Financial Relativity

June 5, 2024 by Bill Bourbonnais

Time travel is a classic movie staple, to the point where you can hardly venture into your neighborhood metroplex without seeing someone in a rush to get to the past or the future. In The Terminator, Skynet sent a Cyberdine Systems Model 101 (aka the T-800, aka Arnold Schwarzenegger) into the past to kill John Connor’s mother. In Back to the Future Part II, Marty McFly drives his DeLorean 30 years ahead to save his son from sabotaging his family’s future. And in Avengers: Endgame, the gang goes back to 2012 New York to steal the Time Stone, Mind Stone, and Space Stone to keep Thanos from snapping his finger and exterminating half of all life in the universe.

Former Baltimore City prosecutor Marilyn Mosby committed fraud, against her future self. That may sound melodramatic in a movie trailer. But should she really be facing punishment for it?

Filed Under: Retirement, taxes Tagged With: tax, tax savings, tax strategy, taxes, wealth tax

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