Every fall, the asks start arriving.
Galas. Year-end appeals. The school capital campaign. The board seat that quietly comes with an expectation. And for a lot of successful business owners, the response is the same every year: write the checks in December, collect the receipts, and let the return sort it out in April.
That habit used to be merely inefficient.
In 2026, it can be expensive.
This is the first tax year under the charitable deduction changes in the One Big Beautiful Bill Act. The rules for how gifts get counted changed. The giving habits of most owners did not. And December 31 is still the date that decides which year a gift belongs to.
Generous owners deserve better than a holiday routine. They deserve a giving strategy.
Why year-end giving looks different in 2026
For tax years beginning after December 31, 2025, several new layers sit on top of the familiar charitable rules.
Itemizers can generally deduct charitable gifts only to the extent they exceed 0.5% of adjusted gross income. An owner with $800,000 of AGI gives the first $4,000 with no federal deduction at all. Small, scattered gifts are the ones most likely to vanish under that floor.
Owners in the top 37% bracket face a second change: the tax value of itemized deductions, including charitable gifts, is generally capped at 35%. The deduction still matters. It is just worth a little less per dollar than it was last year.
C corporations now face their own floor. Corporate charitable deductions generally apply only to gifts above 1% of taxable income, still subject to the 10% ceiling. A company that gives a modest amount each year may find much of it no longer produces a deduction.
Some things did not change. The 60%-of-AGI limit for cash gifts to public charities was made permanent. Gifts of long-term appreciated property to public charities, including donor-advised funds, are still generally deductible at fair market value up to 30% of AGI, with a five-year carryforward for the excess. And for owners 70½ or older, qualified charitable distributions from IRAs, up to $111,000 per person for 2026, still bypass the new floor entirely because they never enter income in the first place.
There is even a new break for people who take the standard deduction: up to $1,000 of cash gifts directly to public charities, or $2,000 on a joint return. It does not apply to donor-advised funds or non-cash gifts. For most high-earning owners who itemize, it is a footnote, not a strategy.
Put together, the message is simple. The Code still rewards giving. It now rewards intentional giving more than habitual giving.
December 31 is the headline. The real opportunity is the diagnosis.
Most owners treat charitable giving as a calendar event.
The appeals arrive. The checks go out. The receipts go in a folder.
That is generosity. It is not yet a plan.
The better question in October is not “How much should I give this year?” It is “What am I giving, through which vehicle, in which year, and what do I want it to accomplish?” A gift completed before December 31 belongs to 2026. A gift that is still a pledge, a promise, or a stock transfer stuck in processing does not.
October is when that question still has room to breathe.
1. “Will my gifts actually clear the new floor—or am I spreading them too thin?”
Start with the math, not the mailbox.
What is your projected 2026 AGI? What does 0.5% of that number look like? How much of your planned giving is a series of small gifts that, taken together, barely clear the floor?
For many owners, the answer points toward concentration. Bunching several years of intended giving into a single year can push more of it above the floor and make itemizing worthwhile. A donor-advised fund can make that practical: the deduction lands in the year the fund is funded, and grants to charities can follow on whatever schedule your family prefers.
2. “Am I giving cash when I should be giving appreciated assets?”
This is the most common missed opportunity among successful owners.
Writing a check from operating cash while holding highly appreciated stock is often the least efficient way to give. Long-term appreciated securities given directly to a public charity or donor-advised fund generally produce a fair market value deduction and avoid the capital gains tax that a sale would trigger.
For closely held business interests, real estate, or other non-public assets, the opportunity can be larger, but so is the lead time. Qualified appraisals, documentation, and the receiving organization’s willingness to accept the asset all take weeks, not days. That work belongs in October, not the week after Christmas.
3. “Is a liquidity event on the horizon that should change when and how I give?”
Timing around a sale is where charitable planning gets the most leverage—and the least forgiveness.
A year with an unusually large income event can be the right year to fund a meaningful long-term giving vehicle. But the order of operations matters. Gifts of a business interest made after a sale is effectively locked in may not deliver the result owners expect. If a sale, recapitalization, or partial exit is in discussion, charitable planning needs to be part of the deal conversation early—not an afterthought once the LOI is signed.
4. “Does my business’s giving still make sense under the new corporate rules?”
Sponsorships, community gifts, and employee-match programs often run on autopilot.
For C corporations, the new 1% floor means modest annual giving may produce little or no deduction. For pass-through entities, charitable gifts generally flow through to the owners’ personal returns, where the individual floor and limits apply. In both cases, it is worth asking whether the gift is really charitable, really marketing, or some combination—because the tax treatment can differ, and so can the documentation.
What smart business owners are doing right now
The strongest operators treat year-end giving as part of the Q4 plan, not a separate holiday ritual.
They rebuild their AGI projection before they decide how much to give. They look at the 0.5% floor and ask whether bunching makes sense. They give appreciated assets instead of cash where it fits. They open or top up donor-advised funds early enough that transfers settle well before December 31. They start appraisals and documentation for non-cash gifts now. Owners 70½ or older look at qualified charitable distributions before writing checks from taxable accounts. And they make sure every significant gift has the written acknowledgment the IRS expects.
Most of all, they connect giving to the bigger picture: family values, legacy goals, the next liquidity event, and long-term wealth planning.
None of that requires drama. All of it requires October.
The hidden cost of waiting until the last week of December
The holidays are the worst possible time to make careful decisions.
Stock transfers take days to settle, and year-end volume makes them slower. Charities close for the holidays. Appraisers book up. Donor-advised fund sponsors post cutoff dates for gifts of securities that are often well before December 31. Owners who wait end up giving cash because it is the only thing that still moves—and lose the capital gains benefit they could have captured.
Others miss the year entirely. A gift that settles on January 2 is a 2027 gift, no matter when the decision was made.
That is the hidden cost of treating giving as a holiday habit.
You still give. You just give less efficiently than the Code allows—and in a year when the rules already ask more of you.
The Wealthrive view
Charitable giving is one of the few places where tax strategy and personal values point in the same direction.
The goal is not to give less. It is to give on purpose.
The most effective business owners treat philanthropy as part of the same year-round plan as compensation, entity design, retirement, and exit planning. They decide what they want their giving to build, then choose the assets, vehicles, and timing that make every dollar go further—for the causes they care about and for their family’s long-term wealth.
December 31, 2026 is just a deadline.
The bigger opportunity is using the next few weeks to turn generosity into strategy while there is still time to do it well.
Because real tax strategy is not about scrambling to find deductions in December.
It is about building a plan where the things you already care about are working as hard as they can.
Educational only. This article is not tax, legal, or investment advice. Tax rules are fact-specific and change over time, so business owners should review their situation with qualified advisors before acting.
