The Giving Years: Four Answers That Change Everything
At some point, the central question of your financial life quietly changes, from “will we have enough?” to “what do we want it to do?” In our experience, that second question is harder. Not because of the tax code, but because most people have never said the answer out loud.
Two questions, four answers
We ask every family the same pair of questions:
If you died today, how much of your wealth would go to people, and how much to charities or causes you care about?
Of each of those amounts, how much would you like to give now, while you're here to see it, and how much later?
That's it. People and causes, now and later: four answers. Most couples have never been asked, and it's common for spouses to hear each other's answers for the first time in our office. Everything else in a wealth-transfer plan flows from that grid.
Permission to give
The biggest obstacle to giving isn't generosity; it's uncertainty. Before anyone gives comfortably, they need to know it won't compromise their own security. So we model it in planning software: if you gave this amount every year starting now, what does your plan look like at 95? Watching the plan hold up on screen turns “someday” into “this year.” That confidence is often the most valuable thing we provide in this whole process.
Then the math — which often reverses what intuition says
Once the grid is filled in, the question becomes which assets to give, and when. This is where the answers get surprising:
Appreciated stock given to charity (directly or through a donor-advised fund) means nobody ever pays the capital gains tax. But the same stock left to your children gets a step-up in basis at death, and the gain simply disappears. The identical asset has opposite best uses depending on which square of the grid it's funding.
IRA dollars are often the best asset to give to charity and the worst to leave to your kids, who will pay income tax on every dollar within ten years of inheriting. After age 70½, qualified charitable distributions send IRA money directly to charity without it ever touching your tax return. One wrinkle: they can't fund a donor-advised fund, which is exactly the kind of detail that trips up do-it-yourself giving plans.
Cash is the simplest thing to give, and usually the least efficient if you're holding appreciated assets that could do the job better.
The future gift: Roth conversions
There's one more move that belongs in this conversation. Converting IRA dollars to Roth later in life can be the most generous gift you never have to hand over. Your children inherit the most attractive asset on the menu: money that comes to them tax-free, instead of a traditional IRA they'd owe income tax on. And because the money stays yours until the end, it remains your safety net rather than an irrevocable gift.
For Washington families, there's a quieter benefit. A traditional IRA can effectively be taxed twice at death: once under the state estate tax, and again as income to your children, with no deduction at the state level to soften the overlap. Paying the conversion tax during your lifetime shrinks the estate the state can tax and takes that double hit off the table.
Each square of the grid (people now, people later, causes now, causes later) has a best-asset, best-timing answer, and those answers shift as tax law and your life change. Getting them right is the part we love. Saying what you want is the part only you can do.
Walla Walla Wealth Advisors is an investment adviser registered with the State of Washington. This article is for educational purposes only and is not individualized investment, tax, or legal advice. Rules described are current as of July 2026 and may change. Please consult a qualified professional about your specific situation.