Tax season debrief: Three common regrets

A message from the CICF Collaborative, including Central Indiana Community Foundation, Hamilton County Community Foundation, IMPACT Central Indiana, the Indianapolis Foundation, and Women’s Foundation of Indiana

By Robin Elmerick, Sr. Director of Effective Philanthropy

If you’re like many donors, the weeks leading up to tax deadlines bring your charitable giving into sharper focus. You may have finalized contributions, gathered documentation, or talked with your CPA about how philanthropy fits into your financial plan.

Once you file your return, it’s easy to move on. But the weeks right after tax season offer one of the best opportunities to reflect—while the details are still fresh. That reflection matters even more this year, as recent tax law changes continue to affect charitable strategies.

If anything surprised you this tax season, now is the time to take a closer look. Small adjustments made early in the year can lead to better outcomes—both financially and philanthropically.

Here are three common regrets we hear, along with ways to plan differently moving forward.

Giving cash instead of appreciated assets
Many donors use cash or credit cards for larger gifts when they could give appreciated assets such as stocks, mutual funds, or real estate held for more than one year.

The regret: Selling assets first can trigger capital gains tax on the appreciation.
The better move: Donating the asset directly to a fund within the CICF Collaborative or another qualified charity may allow you to avoid capital gains tax and deduct the full fair market value if you itemize.

Missing the opportunity to “bunch” contributions
Higher standard deductions have made it harder for some donors to benefit from charitable deductions each year.

The regret: Spreading donations evenly across multiple years and not exceeding the standard deduction threshold.
The better move: Take a “bundling approach”. Combine several years of giving into one year by contributing to a donor-advised fund within the CICF Collaborative. This approach can help you exceed the standard deduction and take a larger deduction in that year, while still supporting charities over time.

Pro tip: Planning early is especially important right now. In addition to a higher standard deduction, charitable deductions now include a 0.5% “floor” and a 35% cap. Work with your tax advisor early in the year to build the right plan.

Overlooking documentation requirements
Even well-intentioned giving can run into issues without proper records.

The regret: Missing written acknowledgment for gifts over $250 or failing to keep bank records for smaller donations.
The problem: Without documentation, the IRS may disallow deductions—even for legitimate gifts.

The value of a fund: Using a donor-advised fund simplifies recordkeeping by consolidating your charitable giving into a single, year-end tax acknowledgment. Instead of tracking receipts for every individual donation, you receive one comprehensive document—helping ensure you meet IRS requirements while reducing the risk of missing or incomplete documentation.

Other common missteps to avoid

• Missing opportunities to use Qualified Charitable Distributions (QCDs) for those age 70½ or older
• Donating to organizations that are not qualified 501(c)(3) nonprofits (Note: this is not a worry if you’re giving through a fund held with the CICF Collaborative – we do this due diligence on your behalf)
• Overvaluing non-cash donations instead of using fair market value

Looking ahead to next tax season, early planning makes all the difference. The CICF Collaborative can help you think through charitable strategies, avoid common pitfalls, and align your giving with both your values and your financial goals.

If you’d like to talk through your approach for the year ahead, we’re here to help.

About the author

Robin Elmerick, senior director of effective philanthropy has been with CICF since 2019. A certified Impact Philanthropy Advisor, she works closely with fundholders across all entities of the CICF Collaborative to help them define their philanthropic strategies and maximize their impact. With a background in nonprofit leadership and consulting, she is passionate about bridging the needs of the community with the missions of nonprofits and the passions of our fundholders, aligning all three to create meaningful change in Central Indiana and beyond.

About the CICF Collaborative

CICF Collaborative is a partnership of philanthropic organizations working together to strengthen communities across the region. Each entity within the CICF Collaborative (including the cornerstone entities, Central Indiana Community Foundation, Hamilton County Community Foundation, IMPACT Central Indiana, the Indianapolis Foundation, and Women’s Foundation of Indiana) brings deep knowledge, strong relationships, and its own individual, focused mission. The CICF Collaborative unites the entities by providing shared services, allowing the entities to operate more efficiently and effectively. By leveraging what we each do best, we’re able to better serve our communities and create more lasting impact, together. Learn more »