In my last Thoughts on Money a few weeks ago, I wrote about laying the groundwork for compassionate wealth transfer after we pass. That is still one of the deepest responsibilities and reasons for thoughtful planning.
But since writing that piece, I’ve found myself in a different kind of conversation, and I’m starting to see it everywhere: not just in client meetings, but in the broader financial headlines as well. It keeps resurfacing across families, across circumstances, always anchored in the same emotional place.
The wills are signed. The trust structure is sound. The beneficiaries are clearly defined. And yet, just beneath that well-built plan, there is often a quiet, unexpected tension.
Those blessed to live a life of abundance are not solely focused on what they will leave behind. They want to witness the impact of their generosity while they are still here. They want to see a daughter settle into the home that finally feels right. They want to take pressure off a son navigating the financial weight of raising a family today. They want to contribute to a grandchild’s education as it unfolds, not just as a line item in the future. They want their wealth to do something now, in ways that feel immediate and deeply human.
And so, the question shifts. “We’ve been incredibly fortunate to build this. How do we start sharing it today, carefully, without undermining everything we’ve put in place?”
This becomes even more pointed for families tracking their balance sheet against federal estate tax thresholds. In current 2026 analyses, we are working with a $15 million federal exemption per person, or $30 million for a married couple. For families near that range, gifts begin to carry dual weight. They are expressions of love, but they are also technical decisions with long-term implications.
No one wants to hold back unnecessarily. But no one wants to move carelessly either. That is where the planning becomes nuanced, and where the opportunity sits. Because in most cases, there is more flexibility than many realize, and more deliberate ways to begin helping now without compromising what comes later.
SMALL BUT MIGHTY
A surprising number of people do not know how much can move out of an estate gradually and without fanfare. The 2026 annual gift exclusion is set at $19,000 per person, per beneficiary. What does that mean? Entirely separate from that $15 million lifetime exemption, this is an amount that can be gifted in each calendar year without having to file a gift tax return and reduce the balance sheltered from estate tax at death. And the federal government will very likely continue to increase it in future years.
A parent can make annual gifts to a child. A married couple can split their gifts and double the amount transferred. If the child is married, there may be room to gift to their spouse as well. If there are grandchildren in the picture, the circle can widen again. What looks modest on paper can become meaningful when it is repeated consistently.
I often find that clients underestimate the cumulative effect of this. They imagine a gift as a single dramatic event. It certainly can be, but in reality, some of the smartest wealth transfer happens through repetition. A steady amount each year can begin funding a 529, seed a custodial account, capitalize a trust for a grandchild, or simply move assets into a bucket designated for someone else’s future.
And for families with multiple children and grandchildren, that pattern compounds quickly. In one recent recommendation, the practical advice was that a married couple could write a $38,000 check to each child, each child’s spouse, and each grandchild, assuming the gifts were structured properly between spouses. That generosity moved $456,000 outside of their taxable estate without reducing their lifetime exemption and helped fund a mix of current home renovations, future education costs, and once-in-a-lifetime travel.
I like this category of planning because it does not feel like a stunt. It feels like alignment. The estate plan says, “These people matter.” Annual gifting starts to live that truth now.
BIG BUT SMART
Okay, but what if a larger gift is on the table? The house. The business opportunity. The lifeline.
This is where families often feel stuck. They want to help with something substantial, but they do not love the idea of simply wiring a massive amount and reducing lifetime exemption unnecessarily. Or they want to help a child acquire an asset in a way that feels right sized for their stage of life. So, intrafamily loans often enter the conversation.
The emotional appeal is obvious. Parents may be able to offer better terms, more patience, and more flexibility than a traditional lender. The child gets support. The family keeps the arrangement private. There is structure, but there is also grace.
When done properly, a note can create a middle path between withholding help and giving money away without a framework. The child can make payments over time. The parents retain the right, if they wish, to forgive amounts gradually in later years using that same annual exclusion. The whole arrangement can be more relational and more intentional than a bank loan.
I think this matters because many parents want to create lift without creating dependence. It requires understanding how to set the rate appropriately and paper the arrangement properly with counsel, but it is remarkably efficient and done far more frequently than many may realize.
CARE NOT CASH
There is another category of generosity that families are often drawn to because it feels highly purposeful. I am talking about paying for the thing itself. School. Medical costs. A need that is concrete and visible.
This kind of support often feels emotionally cleaner to parents and grandparents because it is tied to a real burden. It is less abstract than “here is money” and more like, “Let me carry this part for you.”
That distinction matters. The goal is not always simply transfer. It is stewardship. Parents want to help in a way that supports progress rather than excess. Paying for something specific can preserve that tone. It can make the generosity feel less like a windfall and more like reinforcement.
In many cases, payments directly to an institution on behalf of a loved one do not count as gifts, so they can occur above and beyond annual exclusion gifts, provided the payment is made directly to the qualifying education or medical provider. If you write a $50,000 check to a university and pay $10,000 to a hospital, you could still potentially gift $19,000 to the same individuals who benefitted from those direct payments. For this reason, we sometimes recommend not funding 529s, especially if a client lives in a state where the contribution does not generate a deduction, and instead diverting those funds to a custodial or trust account while planning to pay education expenses directly.
I find that these types of solutions can bring surprising relief. A child may hesitate to ask for broad financial help. It can feel exposing. It can feel like failure. But help with tuition, medical costs, or childcare often lands differently. It feels concrete. It feels earned by circumstance. It feels easier to receive.
FEDERAL NOT THE FULL STORY
At this point, some readers may be tempted to tune out. This all sounds nice, but you may not be sitting on a huge federally taxable estate. Fair enough. Still, I would not dismiss the relevance too quickly.
For one thing, no one can say with certainty where federal estate tax thresholds will land over the span of a lifetime. Planning that feels sufficient today can look very different years from now, especially if the rules tighten. And federal law is only part of the story.
Where things become more interesting, and often more consequential, is at the state level. Several states impose their own estate or inheritance taxes, and the thresholds can be lower than what exists federally. In those environments, families who would never consider themselves exposed to federal estate tax may find themselves navigating a very real state-level liability.
At the same time, most of those states do not apply a separate gift tax in the same way. That creates a subtle but important dynamic. Assets transferred during life may reduce the size of a taxable estate without triggering a corresponding state-level tax at the time of the gift. That distinction rarely shows up in headlines, but it has a real influence on how and when families choose to move wealth. It also reinforces a broader point: this is not a one-size-fits-all conversation. The answer changes depending on where you live, how your assets are structured, and what your long-term priorities look like.
Some families operate in a landscape with no state estate tax at all. Others are navigating a much tighter set of constraints. The difference between those two realities shapes behavior and informs timing. It changes the way people think about what to hold, what to shift, and when to act. Which is why it is worth resisting the urge to treat this as a purely federal exercise.
NOW NOT LATER? OR NOW…BUT ALSO LATER?
Many people spend years building a plan that says, “One day, this wealth will bless the people I love.” Then comes the realization that maybe one day is not the only day that matters. Perhaps the better question is whether part of that blessing belongs here, in the middle of life, when support would be felt in real time.
I do not think generosity becomes wiser simply because it is delayed. But I also do not think generosity becomes wiser simply because it is immediate. The sweet spot is giving in a way that aligns with the estate plan rather than fights against it, strengthens the family rather than destabilizes it, and uses the tools available without becoming obsessed with the tools themselves.
Sure, the documents matter. The tax math matters. The structures matter. But beneath all of it is something much older and more human. Parents want to help. Not someday in theory. Now, while they can watch it do some good.
Matt Gregory
Director, Planning
Trevor Cummings
PWA Group Director, Partner
