Charitable giving
You already know what you want to support. My job is the mechanics: which asset to give, from which account, in which year, so the same generosity either costs you less or delivers more.
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Nobody gives for the deduction. You give to the people and causes you love: your kids and grandkids, your church, your alma mater, the organization that stood by your family when it counted. I'm not here to talk you into giving to charity. My aim is to help whatever you choose to give land with the most impact and the least waste, and wherever possible, while you are still here to enjoy the difference it makes.
Then comes the part I can help with. The same generosity can cost you very different amounts depending on which asset you give, which account it leaves from, and which year it lands in. Cash is the easiest way to give, and for many givers it's also the most expensive.
Some of the most rewarding giving never reaches a charity at all. It goes to your own family, and when it goes counts as much as how much. By the time many people pass their wealth on, their children are themselves in their sixties and comfortable. It was the younger versions of those children, the ones raising families on a stretched income, who could have felt the help most. Money is meant to be enjoyed, and there is far more enjoyment in giving to family while you are alive to watch it change something than in never seeing the difference it makes.
There are important tax angles to weigh alongside all this, like the step-up in basis your heirs receive on assets you hold until death, so timing a family gift well is its own conversation. What stays constant is the aim: not to move your money toward charity, but to draw the most satisfaction from your own money and legacy, on your terms, while you can still feel it. Sometimes that surfaces a thought exercise. A person might find more total meaning in leaving 99 percent to their children and 1 percent to a cause they love than in leaving that final slice to the kids as well. There is no right answer there, only yours, and those are exactly the conversations I enjoy having.
Because the tax break is doubled. Give shares you've held more than a year and, under longstanding IRS rules, you can generally deduct the full market value while never paying capital-gains tax on the growth. The charity sells the shares tax-free, and if you loved the stock, you can buy it back with the cash you would have donated.
This works with nearly any sizable charity, and a donor-advised fund can bridge to the small ones: the fund accepts your shares, sells them tax-free, and sends the charity a check.
Separating the tax decision from the giving decision. You contribute to the fund in a year when the deduction helps most, take the deduction then, and grant the money to charities on whatever schedule feels right, this year or over the next decade. Bunching several years of giving into one contribution is the classic move.
Bunching exists because of the standard deduction. In years when your itemized deductions fall just short of it, charitable gifts add nothing to your return. Stack a few years of giving into one contribution, itemize that year, take the standard deduction the others, and every charity still receives its usual gift on its usual schedule.
A gift straight from your IRA to charity, available once you're 70 1/2 under IRS rules. The amount never shows up in your income, and once required minimum distributions begin, it counts toward them. For retirees who take the standard deduction, it's often the most tax-efficient giving available, because exclusion beats a deduction you can't use.
The mechanics decide whether it counts. The custodian must pay the charity directly, the money can't pass through your hands first, and year-end transfers need time to clear. I handle those details with you so a generous idea doesn't become a taxable mistake.
High-income years, when you can choose. A business sale, a big bonus, a heavy vesting year, or a large Roth conversion all push you into higher brackets, and a well-timed gift offsets income that would otherwise be taxed at your highest rate. Giving the same amount in a low-income year buys a smaller tax benefit.
This is also where giving meets the rest of the plan: sale years, vesting years, and conversion years are exactly when we look hardest at a larger gift or a donor-advised fund contribution.
Consider how giving, taxes, and family can line up in a single year. Say you gift appreciated stock to an organization you believe in. The deduction that creates can offset the tax on a larger Roth conversion in the same year, so more of your IRA moves to tax-free ground at little net cost. The cash you would have donated stays with you, carrying no capital gain, and you hand it to your daughter, the one with three kids and a single income who could use it far more now than at 65. One year, three moves: a cause you care about is supported, your future taxes shrink, and your family feels the help while you are here to see it. The exact figures turn on your brackets and holdings, which is the part we map together.
Who each door tends to fit. Many families end up using two or three of them in the same year.
| Way to give | Tax effect | Complexity | Often fits when |
|---|---|---|---|
| Cash | Deductible only if you itemize; no other benefit. | None. Write the check or tap the button. | Smaller gifts, or years when you itemize anyway. |
| Appreciated stock | Typically deductible at full market value for shares held over a year, with no capital-gains tax on the growth. | Modest. The charity or a donor-advised fund receives the shares by transfer, which I help arrange. | You hold winners in a taxable account and give meaningful amounts. |
| Donor-advised fund | Deduct in the year you contribute; grant to charities on your own schedule afterward. | Moderate. One account to open, then giving gets simpler every year. | Bunching deductions, a high-income year, or organizing a family's giving. |
| QCD from an IRA | Excluded from income entirely and counts toward required minimum distributions. | Modest, but the paperwork must be exact: the IRA custodian pays the charity directly. | You're 70 1/2 or older, give regularly, and take the standard deduction. |
Jesse Plunkett, CEPA®, CRPC®
Financial advisor in Sanford, FL, serving clients across the country virtually. Meet your advisor, or check my record on 
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A quick, useful starting point
1. Named beneficiaries override your will Beneficiary listings on investment accounts override your will entirely. Named an ex-spouse or a late parent? They still inherit, no matter what your will says…
A short, low-key call. Tell me what you support and how you give today, and we'll see what a tax-smart version could look like.
A charitable account you fund now and give from later. You contribute cash or, better, appreciated investments, take the tax deduction in the year of the contribution, and then recommend grants to charities whenever you choose. The money can stay invested while it waits. Think of it as a giving account with the tax paperwork built in.
A qualified charitable distribution sends money directly from your IRA to a charity. IRS rules make it available from age 70 1/2, and the amount is excluded from your income entirely, which helps even if you never itemize. Once required minimum distributions start, QCDs count toward them, so the giving you already do can also satisfy what the IRS requires.
Usually, if the stock has grown and you've held it more than a year. You generally deduct the full market value, nobody pays capital-gains tax on the growth, and the charity receives the same amount. If you still like the investment, repurchase it with the cash you would have given; you'll own it at a higher cost basis.
Yes, through a qualified charitable distribution. Money sent directly from your IRA to charity counts toward your required minimum distribution but never lands in your income, so it can lower the taxes the RMD would otherwise create. It can also help downstream numbers that key off income, like how much of your Social Security is taxable.
It depends on your numbers, but giving now is underrated. Heirs often inherit in their own sixties, already settled, while the younger version of them, raising kids on a tighter budget, would have felt the help far more. Giving while you're alive also lets you watch it make a difference. The main things to weigh are whether you'll comfortably have enough for your own life first, and the step-up in basis your heirs get on assets held until death, which can favor passing highly appreciated investments at death and gifting cash during life. We map the trade-offs to your situation.
No, and I think that's the right boundary. The causes are yours: your church, your alma mater, the organization that showed up for your family. You bring the who and the why. I organize the how: which assets to give, from which accounts, in which years, so the same generosity costs you less.
Almost always. Everything is handled virtually, so where you live is rarely a barrier. The only exception is a handful of states where I'm not registered yet, and if that's you, I'll tell you on our first call.