Postmark changes, client anxiety, retirement case study, tax time scenarios, and insights about women & philanthropy

Postmarks, rule changes, and clients’ 2026 charitable gifts

If you were surprised to read about the ripple effect of a seemingly small change in the U.S. Postal Service regulations late last year, you were not alone! Here’s what you need to know:

What’s the background with the IRS?
Under long-standing IRS guidance, a charitable contribution is generally considered “made” for tax purposes when the donor irrevocably parts with control of the gift. For contributions made by check and sent through the mail, the IRS has traditionally treated the date of the U.S. Postal Service postmark as the date of the gift, even if the charity receives the check later. This approach is reflected in IRS Publication 526 and generally parallels the broader “mailbox rule” under Internal Revenue Code Section 7502, which treats certain documents and payments as timely based on their postmark date rather than the date of receipt.

Okay, so if this is not an IRS issue, what happened?
In November 2025, the U.S. Postal Service (not the IRS) changed how postmarks are applied. Effective December 24, 2025, the official postmark date is now defined as the date of the first automated processing scan at a USPS processing facility, rather than the date a letter is dropped in a mailbox or handed to a clerk at a local post office. As a result, mail deposited on December 31, 2025, may not have actually received a postmark until several days later, especially around the holidays. This change took many people by surprise and created a lot of confusion, prompting the USPS to issue a “facts and myths” circular.

So, what’s this got to do with the IRS?
Because the IRS’s practices continue to rely on the postmark to establish the date of a mailed charitable gift, this change can cause a contribution a client intended to deduct for a particular year to be treated as a contribution for the following year if the postmark reflects a January processing date.

What should clients do for 2026 and beyond?
Advisors should counsel clients on how to avoid this issue going forward. Electronic giving methods such as online donations, ACH or wire transfers, and completed transfers of publicly traded securities provide clearer and more immediate timestamps for deduction purposes and do not depend on postal processing practices.

How can GiveWell Community Foundation help?
Reach out to our team early in the year! Many clients find themselves rushing around at year-end to make charitable donations. The change in the postal rules is a terrific reason to remind a client that organizing charitable giving through a donor-advised fund allows the client to make a donation for tax purposes to the donor-advised fund well before the end of the year, thereby securing any applicable charitable deduction, and then recommending grants from the donor-advised fund anytime to favorite charities.

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Behind clients’ anxiety: It’s not all because of taxes

It’s not unusual to be on edge during tax season. Research suggests that one in three taxpayers report that the thought of filing taxes makes them want to cry! The dread of owing money, the complexity of reporting requirements, and the anxiety of waiting for a refund can take its toll. What’s more, one survey found that 75% of senior accountants say that tax season is stressful.

This is not particularly surprising. What’s important for professional advisors to recognize is how that stress might appear to spill over into other areas of clients’ financial lives. Charitable giving is one of those areas. For example, it may seem like tax time anxiety makes clients reluctant to discuss their charitable giving plans for the rest of the year, even though you know that it’s best to line up a strategy early.

But it may not be tax season stress that’s causing your clients to procrastinate charitable giving decisions. Not every client who is on the fence about charitable giving is wringing their hands over taxes! In fact, many of the most common obstacles are emotional and behavioral: lack of trust in how nonprofit organizations will use the funds, fear of losing control, uncertainty about family dynamics, anxiety about timing, or decision paralysis in the face of just too many choices.

The Community Foundation can help. For example, if control is the issue, clients may feel more comfortable when they understand they can start with a flexible structure. A donor-advised fund at the Community Foundation allows a client to make a contribution when it makes sense financially, then recommend grants over time. Even clients who are not ready to decide which organizations to support can still take the first step and build momentum.

If the client’s concern is family dynamics, working with the Community Foundation team can help you provide a forum for participation that does not require disclosing sensitive financial information. Many clients want to involve children or grandchildren in giving decisions, but they are hesitant to share the details of their wealth despite the benefits of doing so. Charitable conversations can allow family members to engage with the “why” without focusing on the “how much.” Over time, this can strengthen family unity and reduce conflict around legacy intentions.

If the client is anxious about timing and making too many decisions too soon, charitable planning can be framed as an evolving journey rather than a single, permanent choice. Working with the Community Foundation, a client can start by supporting a small set of organizations or a broad cause area and then refine focus as confidence grows. Clients often feel relief when they realize that generosity does not require perfect certainty to begin.

Finally, if the client is simply overwhelmed by options even for future giving, the Community Foundation’s expertise can help simplify the decision process. We can share information about community needs, provide research on organizations, and help clients understand how different types of funds can match different levels of desired involvement. This reduces the burden on the client and allows you, as the advisor, to keep the conversation moving forward without turning it into a lengthy research project.

The common theme is that proactive charitable planning can address the real barriers—control, family, timing, or overwhelm—while still supporting sound tax and estate planning. The professional staff at the Community Foundation are here for you and your clients—during tax time and anytime!

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Retirement and legacy: A case study

Recently, we were asked by a financial advisor to describe in more detail how to actually have conversations with clients integrating charitable planning into retirement planning.

Let’s say your clients, Andy and Nancy, come to your office to check in on their retirement planning.

At 69 and 68, Andy and Nancy want clarity in all areas of their financial plan—income projections, healthcare costs, and portfolio sustainability for the next 25 to 30 years. You walk them through cash-flow models, distribution strategies, and conservative market assumptions.

The numbers hold up but as often happens, once the spreadsheets are settled, the deeper conversation begins.

Andy and Nancy have always been charitable—primarily through year-end gifts to a dozen or so favorite nonprofit organizations and occasional larger contributions to capital campaigns—but they’ve never fully integrated philanthropy into their financial plan. Now, with retirement approaching, they want to be more intentional. At the same time, they are cautious.

You begin by showing them how charitable planning can align with their income strategy rather than compete with it. When Andy turns 70 ½, Qualified Charitable Distributions (QCDs) from his IRAs can help keep those dollars out of taxable income. Nancy can do the same when she reaches 70 ½.

Andy and Nancy can make Qualified Charitable Distributions to public charities, including certain types of funds at the Community Foundation. The limit for 2026 is $111,000 per taxpayer, and that amount will be adjusted each year for inflation. The QCDs will bypass their adjusted gross income altogether and go straight to the charitable organization.

Based on the numbers you showed them, they won’t need any income from their IRAs to cover living expenses. Their other investments will more than cover everything they plan to do in their retirement years.

Next, you move to the subject of Andy and Nancy’s annual charitable giving. They are already doing a lot of charitable giving, so it makes sense for them to consider establishing a donor-advised fund. They’ll be eligible for a charitable deduction this year, and the fund can support their favorite charitable organizations for years to come.

Andy and Nancy hold a total of $2 million in traditional IRAs and $4 million in a non-retirement brokerage account. Their two adult children are in their peak earning years, both in the 35% federal bracket and roughly 5% state tax.

For illustration purposes, if the kids were to inherit the IRAs today, they’d need to withdraw the full balance within ten years. If they pulled it out in the first year, at a combined 40% tax rate, that $2 million could trigger somewhere in the neighborhood of $800,000 in income taxes. Using a rough estimate, hypothetically, they’d net about $1.2 million.

Here’s the alternative.

Instead of naming the children as IRA beneficiaries, Andy and Nancy could designate their donor-advised fund at the Community Foundation as the beneficiary. As a public charity, the fund would receive the full $2 million free of income tax creating a charitable legacy for the family.

In this rough hypothetical situation, the kids would still inherit the $4 million of brokerage assets. Those assets receive a step-up in basis at death. Right now, because Andy and Nancy held many of these positions for a long time, the unrealized capital gain is about $1 million, and that gain ‘disappears’ when they die because of the step-up. If the children were to sell immediately after inheriting the accounts, there may be little or no capital gains tax due.

In this hypothetical scenario, if Andy and Nancy died tomorrow, their kids could inherit nearly the full $4 million in the brokerage account, and their charitable fund receives the full IRA balance.

By connecting Andy and Nancy with the Community Foundation ahead of time, our professional staff can play a complementary role in this plan, administering the donor-advised fund and providing local expertise to help translate charitable intent into lasting impact.

For many clients, it’s not just about the ability to retire, it’s considering how they can still continue to support the organizations and causes they care about well into the future, even when they are gone, creating a family legacy.

As you work with clients like Andy and Nancy, remind them that philanthropy isn’t an afterthought. It’s an important strategy that can be woven strategically into a client’s plans for retirement and leaving a legacy. Our team is here to help!

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Three tax time scenarios, helpful tips, and what you need to know right now

For decades, April 15 has been etched firmly in the minds of both taxpayers and their advisors. As professional advisors, you know that tax season is when many clients start paying closer attention to the rules and how they might have changed since the year before, including rules for charitable deductions.

Especially in light of the tax law changes that took effect on January 1, now is the time to understand clients’ philanthropic intentions for 2026 if you don’t already. Addressing charitable planning at tax time can help ensure that your clients won’t miss out on important opportunities. Here are three ways to do that:

Evaluate QCDs sooner rather than later
Here’s a typical scenario: Your client, who enjoys giving to favorite nonprofit organizations, is 75 years old.

Here’s the tip: Talk with your client as soon as possible about Qualified Charitable Distributions. IRA owners who are 70 ½ and older are eligible to use their IRAs to distribute up to $111,000 in 2026 (indexed for inflation) directly to a qualified public charity, including some types of funds at the Community Foundation. QCDs can satisfy all or part of a client’s RMD.

What’s super important to know right now: Planning QCDs early in the year helps avoid administrative delays and ensures proper coordination with RMD requirements. For clients who do not itemize deductions, especially considering the continued higher standard deduction amounts, QCDs remain one of the most tax-efficient ways to give.

Watch for charitable opportunities in business succession planning
Here’s a typical scenario: Your client is beginning to explore exit strategies for a family business.

Here’s the tip: Contact the Community Foundation early in the planning process. Gifting closely-held business interests to a donor-advised fund at the Community Foundation prior to a sale can be a powerful planning strategy. The client may receive a charitable income tax deduction (generally equal to the fair market value of the gifted interest if it is long-term capital gain property, subject to AGI limitations). The gifted portion of the business may avoid capital gains tax when a sale occurs, maximizing proceeds flowing into the donor-advised fund to support the client’s philanthropic goals.

What’s super important to know right now: Timing is critical. If a sale is already effectively in motion—or if there is a binding agreement in place—the IRS may challenge the charitable deduction under the assignment of income doctrine. Early coordination among legal, tax, and philanthropic advisors is essential.

Consider gifts of appreciated assets early in the year
Here’s a typical scenario: A client who itemizes income tax deductions experienced significant portfolio gains in 2025 and anticipates continued market strength in 2026.

Here’s the tip: Consider recommending that your client make a gift of appreciated stock to a donor-advised fund at the Community Foundation. Gifts of long-term appreciated assets to a donor-advised fund are generally deductible at fair market value (subject to 30% of AGI limitations for appreciated assets, as well as the new floor and cap that took effect on January 1, 2026). The donor-advised fund can sell the asset without incurring capital gains tax.

What’s super important to know right now: Pay particular attention to the rules that apply to clients who itemize their deductions versus those who don’t. Beginning with the 2026 tax year, non-itemizers are eligible to deduct cash gifts (not gifts of stock or other assets) to public charities (excluding donor-advised funds) up to $1000 for single filers and $2000 for joint filers.

As always, our goal at the Community Foundation is to serve as your go-to sounding board on all matters related to charitable giving as you structure clients’ tax, estate, retirement, or business planning strategies. We look forward to working together during tax season and beyond!

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Women and philanthropy: Four insights to inform your practice

At GiveWell Community Foundation, we’re honored to work with hundreds of individuals, families, and businesses who support a wide range of charitable causes. Generosity and commitment across generations and demographics inspire us every single day.

Increasingly, women are leading charitable decisions in their families, with two scenarios driving this change:

  • In many families, a leadership shift happens gradually. For example, a daughter becomes more engaged over the years in conversations about the family’s charitable giving. Or a spouse who traditionally deferred philanthropic decisions begins to shape priorities more directly.
  • In other cases, the transition is sudden and deeply personal—often following the death of a spouse or parent—when a woman assumes sole responsibility for stewarding both financial assets and charitable intent.

Here are four examples of how your awareness of these trends can play out in your day-to-day practice:

Help your clients give through thick and thin.
According to the Women Give 2024 study, over the past two decades, single women experienced a smaller decline in charitable participation than single men, and their average giving amounts held steadier or increased in certain contexts (e.g., secular causes during COVID-19). Be aware of this trend as you represent single women; it may be a priority for them to continue giving even when times are tough. The Community Foundation can help you develop a charitable giving plan to enable women-led philanthropy to continue through life’s ups and downs.

Discuss national trends and local needs.
According to the Women’s Philanthropy Institute at Indiana University’s Lilly Family School of Philanthropy, for the first time, between 2022 and 2023, giving to women’s and girls’ organizations surpassed 2% of overall charitable giving. This represents over $11 billion going to women’s and girls’ organizations in each of these years. This trend is worth mentioning to clients, especially with the help of the Community Foundation team to share parallel local trends and opportunities to make an impact.

Ask about all forms of philanthropy.
According to the 2025 Bank of America Study of Philanthropy: Charitable Giving by Affluent Households, 43% of affluent households volunteered in 2024, up from 37% in 2022—volunteers tend to give more and support causes more deeply, a pattern often stronger among women. Be sure to ask your female clients about causes they support both financially and through volunteerism.

Tailor advice for single women.
Research shows that participation trends vary by household type, with single women maintaining more consistent giving patterns over long periods. Pay particular attention to building thoughtful charitable giving plans for single women households. The Community Foundation can help maximize both impact and financial planning goals as you serve these clients.

As is the case when you are working with any charitable client, our team is honored to be your partner. Whether your client is establishing a new structure, building a comprehensive strategy around an existing donor-advised or other type of fund, or navigating inherited philanthropic responsibilities, we are here to help ensure their giving reflects both enduring legacy and evolving purpose.

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The professional staff at GiveWell Community Foundation is a resource and sounding board as you serve your philanthropic clients. We understand the charitable side of the equation and are happy to serve as a secondary and trusted source as you manage the primary relationship with your clients. This newsletter is provided for informational purposes only. It is not intended as legal, accounting, or financial planning advice.  

Ready to get started?

You know your clients. We know philanthropy. Together we can ensure your clients make the best decisions for making a difference in the community.

Lori Martini

Lori Martini

Vice President/CPO
863-683-3131
lmartini@givecf.org

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