The Steward's Long View: Planning Generosity Across 30 Years, Not One Tax Year
A couple in their mid-fifties sits down in early December to settle the year's giving. He sold a minority stake in the family business last spring, so income is high, and they want to know how much to give and what it will do to the tax bill. Their CPA runs the numbers. They write the checks, file the receipts, and feel good about it. In January the whole exercise starts over.
That ritual is how most families give, and it works well enough for one year. The trouble is that generosity does not run on a one-year clock. Cerulli Associates projects that $124 trillion will change hands in the United States through 2048, with about $18 trillion of it headed to charity. Money at that scale moves through retirement, through death, and into the next generation's hands. The steward's long view treats giving the same way, as a thirty-year plan rather than a December task.
Why the One-Year View Keeps Families Stuck
The tax code makes a poor planner. In 2026 a new 0.5% floor trims the first slice of an itemizer's giving, a 35% cap reduces what each dollar returns at the top bracket, and the estate exemption has settled at $15 million per person. Families who set their strategy by this year's rules are re-deciding every January, and the rules will move again.
A year-by-year view also hides what is happening across a lifetime of giving. According to PG Calc's reading of the Giving USA 2026 report, Americans gave $617 billion in 2025, and charitable bequests jumped about 17%. A large share of giving happens at the end of a life, which is the one place an annual plan never reaches.
Left alone, the one-year habit tends to produce the same three costs:
- Gifts go out in whatever asset is handy. Cash leaves the account in December when appreciated stock would have done more good for the same gift. - High-income years pass unused. The year of a business sale or a large bonus is the best year to give, and it only arrives with a plan already in place. - The final gift is left to the will. What happens to a donor advised fund, an IRA, or a policy at death gets decided by default instead of by design.
What Scripture Says About Time Horizons
The Bible has no tax code to speak of, but it has a lot to say about planning. Proverbs puts it plainly: "The plans of the diligent lead surely to abundance, but everyone who is hasty comes only to poverty" (Proverbs 21:5, ESV). A December scramble is a hasty plan even when the gift is generous.
Jesus asks a question that every long-range giver should hear: "Which of you, desiring to build a tower, does not first sit down and count the cost, whether he has enough to complete it?" (Luke 14:28, ESV). Counting the cost of a thirty-year commitment is not a lack of faith. It is how a pledge gets finished.
The Psalmist asks for the same posture: "So teach us to number our days that we may get a heart of wisdom" (Psalm 90:12, ESV). And Proverbs reaches past a single lifetime: "A good man leaves an inheritance to his children's children" (Proverbs 13:22, ESV). That is a multi-generation horizon, and stewardship in Scripture has always been about managing what is entrusted to you for longer than you will be around to see it.
Three Decades, Three Jobs
Picture a donor who starts the plan at 55. The thirty years that follow break into three stretches, and each has a different job.
### Years 1–10: Build the Engine
These are usually the highest-income years, and the work is to build the vehicle that will carry giving through the rest of the plan. That means opening and funding a donor advised fund in the years income spikes, giving appreciated stock instead of cash, and stacking several years of gifts into one so the deduction clears the new floor. It is also the decade to write down why the family gives. A family giving mission statement takes an afternoon and saves years of drift.
### Years 11–20: Spend the Engine Well
Income often falls at retirement, which changes what a deduction is worth. This is the stretch where giving shifts toward the tools that do not depend on a deduction at all. After age 70½, a qualified charitable distribution sends money from an IRA straight to a charity, and the floor has no say in it. The donor advised fund keeps making grants on a steady schedule while the family's attention turns to what comes next, including who succeeds you as the fund's advisor.
A thirty-year plan has to be built around your actual assets, your actual income curve, and the kids who will inherit the result. Generic timelines only get you part of the way.
What would this look like for you? A Clarity Call is 30 minutes with a Partner, your numbers in front of us, no pressure to act.
### Years 21–30: Release What Remains
The last stretch is about what the family keeps and what it releases. Pre-tax retirement accounts are often the most expensive asset to leave to children, because heirs owe income tax on them, while a charity owes nothing, and the rules for inherited IRAs make that math worth revisiting. A charitable trust can turn a concentrated asset into income for life and a gift at the end. And what happens to your DAF when you die should be a decision you made, not a default the sponsor applies.
The dollars involved at this stage tend to be the largest of the whole plan, which is why they deserve the most lead time.
What Changes Along the Way
No thirty-year plan survives contact with real life untouched, and it should not have to. Markets rise and fall, a business sells earlier than expected, a child's circumstances change, and a spouse's health shifts what the family wants to do. Congress will rewrite the deduction at least a few more times before the plan is finished.
The long view absorbs all of that because the structure is built for it. A donor advised fund lets you give in a good year and grant in a lean one. A written mission statement tells the next generation which causes the family chose and why. A named successor keeps the money moving when the original donor cannot. Each piece is flexible on purpose, which is what makes a decades-long commitment realistic instead of brittle.
What does not change is the question underneath the plan: what has this family been entrusted with, and what does it want that to do after the people who built it are gone?
A One-Page Plan You Can Draft This Quarter
You do not need a forty-page document to start. One page is enough, and it can be done in a single sitting with your spouse and your advisors.
1. Name the total. Write down what you hope to give over the next thirty years, in a single number, before anyone opens a tax spreadsheet. 2. Split it into three buckets. Estimate what you will give during your high-income years, during retirement, and at death. 3. Match each bucket to an asset. Appreciated stock and a DAF for the early years, IRA distributions for the middle years, retirement accounts, trusts, or a policy for the last. 4. Mark the trigger events. A business sale, a retirement date, the first required distribution, and the day a child becomes a co-advisor are all moments to revisit the plan. 5. Choose a review date. Pick one date each year, ideally in the fall while there is still time to act, and put it on the calendar with your CPA and advisor.
The first draft will be rough. That is fine. A rough plan reviewed every year beats a polished plan nobody opens.
The Gift Behind the Long View
A family that gives by the tax year is always responding to someone else's calendar. The floor changes, the cap changes, the deadline arrives, and the gift is shaped by whatever the year allows.
A family that gives by the decade decides first and then asks the tax code to help. The gifts are timed to the years that suit them, held in the right assets, and finished at the end by design. Their generosity does not rise and fall with Congress.
Start with the page. Put the number on it, sort it into three decades, and let the first review date arrive on its own schedule. Thirty years from now, the plan will have done more good than any single December ever could.
The one-page plan is a starting point. Turning it into a funded, tax-aware structure is where the details matter, and every family's version looks a little different.
Is your current giving structure doing what you think it's doing? Most people find out the answer is "almost, but not quite." A Clarity Call closes that gap — 30 minutes, your real numbers, an honest read.
Luke Lyles is a Partner at Sage & Main who works with business owners, families, and their advisors to turn intentions on paper into plans that are actually funded.
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