
I’m excited to share my fourth newsletter featuring a 2025 Giving Guide on Aligning Your Time, Money & Impact.
If you find this valuable and would like to explore how charitable giving can be integrated into your financial picture, please reach out to schedule a time to speak!
Intro

I lost my job at Lehman Brothers in January 2009 during the depths of the Global Financial Crisis. Yet what stands out from the months that followed was not networking or job hunting, but the time I spent volunteering at a soup kitchen near Times Square in NYC.
Giving has been one of the most personally meaningful experiences in my life. With year-end approaching, I wanted to share reflections on giving, how I think about giving time versus money and several tax-aware ways to structure financial gifts based on current rules.
Scroll down to expand on the following:
- Why give?
- Giving time versus giving money?
- A personal reflection after Lehman Brothers
- Tax-aware ways to give financially
- Bringing it all together
Giving started as something I learned from my parents and at church to help others and pay it forward. Over time, I realized I was benefiting just as much from the perspective, fulfillment and sense of purpose it created.
As my daughter says, it “fills up my bucket” in a way few other things do. As I get older, I value that more.
While tax-aware planning may help make giving more efficient, the true return is often not financial. I’ve found that it’s the meaning, connection and purpose the gift creates.
Giving time allows you to see impact firsthand and gain perspective through the people you meet.
Giving money can be equally meaningful, and for charities it is often a more scalableresource. Financial gifts may help sustain programs, expand services and support long-term stability. Depending on your situation, there may also be tax-aware ways to structure charitable giving under the current IRS framework.
Both forms create value. I’ve found that time may build increased connection while money may help scale impact.
After losing my job at Lehman Brothers, I spent several mornings each week volunteering at a soup kitchen near Times Square.
As the Global Financial Crisis was unfolding in the summer of 2008, I remember a friend telling me that if he ever lost his job, he planned to volunteer at a particular soup kitchen near Times Square. He ultimately did not lose his job — but I did in January 2009, so I decided I would volunteer there myself.
At the time, my career prospects were uncertain, but that perspective only made the experience of giving my time feel more meaningful. I served meals, cleaned up afterward and got to know the staff, volunteers and guests. The friendships that grew from that experience became some of the most enduring relationships from my 20 years in New York City.
That season reinforced for me that giving time can create a sense of connection, grounding and purpose in a way that financial giving alone may not.
Paying by credit card is not the only way to give financially. Depending on your circumstances, there are several tax-aware approaches that may help increase the impact of your giving while aligning with your financial plan under the rules in effect today.
Donate Appreciated Stock Instead of Cash?
Donating appreciated stock directly to a charity (instead of cash) may be a more tax-aware way to give because of how the IRS currently treats gifts of long-term appreciated assets:
- Potential to avoid capital gains tax: A direct gift of long-term appreciated stock may allow you to avoid realizing gains that would occur if the asset were sold first.
- Possible fair-market-value deduction: If you itemize and meet IRS requirements, you may be eligible for a deduction based on the asset’s fair market value, subject to AGI-based limits.
- More of your gift may reach the charity: Qualifying charities generally do not pay capital gains tax when selling donated securities.
- Streamlined giving through a DAF: A Donor-Advised Fund may centralize giving, simplify record keeping and accept appreciated securities.
Employer Matching
- If your employer offers matching contributions, using the full match may increase your gift’s impact. Review your employer’s guidelines for eligibility and timing.
Donor-Advised Funds (DAFs)
- A DAF may allow you to contribute cash or appreciated securities, potentially receive an immediate deduction if you itemize, recommend grants to qualified charities over time and simplify charitable recordkeeping. Some households also bunch multiple years of giving into one tax year to increase potential itemized deductions depending on their situation.
Qualified Charitable Distributions (QCDs)
- For individuals age 70½ or older, QCDs allow direct gifts from a traditional IRA to a qualified charity. QCDs may count toward a Required Minimum Distribution (RMD), are excluded from taxable income and are subject to IRS rules, annual caps and documentation requirements.
Gifts of Real Estate, Business Interests and Legacy Approaches
- Depending on your goals, charitable giving may also involve real estate, closely held business interests, private investments, charitable trusts, bequests or beneficiary designations. These strategies come with specific IRS valuation and substantiation requirements and may support philanthropic goals while aligning with estate or transition planning under the rules currently in place.
A thoughtful giving approach blends:
- Why you give
- How you give – whether time, money or both
- What you give – whether cash, appreciated assets or legacy strategies
- How giving fits within your broader financial plan
If you would like to explore how giving might be aligned with your goals, I would be glad to connect!
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