Here’s an uncomfortable question: what if the check you wrote to your church, your alma mater, or your favorite nonprofit last December did nothing for your tax bill? Not because the IRS disallowed it. Because you never cleared the bar required to claim it in the first place.
That’s not a hypothetical for many entrepreneurs right now. It’s the default outcome.
The One Big Beautiful Bill Act (OBBBA), signed on July 4, 2025, permanently locked in the near-doubled standard deduction that the TCJA introduced in 2018 and then raised. For 2026, the standard deduction is $32,200 for married couples filing jointly and $16,100 for single filers. That number isn’t a ceiling you’re allowed to exceed. It’s a floor: every dollar of your itemized deductions- mortgage interest, state and local taxes, and charitable giving combined- has to clear it before any of it starts reducing your taxable income. If your itemizable expenses land under that line, the IRS gives you the standard deduction anyway, and every dollar you gave to charity that year produced exactly $0 in federal tax benefit.
This is where most tax content stops, with a shrug and a “just take the standard deduction, it’s probably better anyway.” That advice is technically true and strategically lazy. There’s a way to keep giving the same amount, spending the same amount on your home, and still clear that bar, just not every single year. It’s called bunching, and 2026’s rules make it more valuable than it’s been since the TCJA first raised the bar in 2018.
What’s below the paywall in this issue:
Exactly which deductions you can legally shift in time, and which ones are stuck wherever they land
How a donor-advised fund lets you claim the deduction now and decide where the money goes later, sometimes years later
The full two-year math: same giving, same spending, $6,300 more in claimed deductions
Why the new 0.5% AGI floor on charitable deductions makes bunching worth more in 2026 than in any year since 2018
The one timing decision that determines whether your bunched deduction is worth 24 cents or 37 cents on the dollar
A six-step checklist to get this set up before December 31
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