Most estate plans answer the question of who will receive your wealth, but far fewer address an equally important one: when might that wealth be most useful?

In this Well Spent feature article, we explore the concept of "giving while living" and why timing may be one of the most overlooked aspects of wealth transfer.

From helping fund education or a first home purchase to creating meaningful family experiences, a gift can have a very different impact depending on when it arrives. As trillions of dollars move between generations over the coming decades, many families are beginning to ask not just what they want to leave behind, but what they might make possible while they're still here to see it.

Giving While Living: What if You Didn't Wait?

Chuck Feeney, co-founder of Duty Free Shoppers, spent much of his life doing something that seemed counterintuitive to many of his peers: he gave away his fortune. By the time of his death in 2023, Feeney had donated more than $8 billion to universities, hospitals, scientific research, and humanitarian causes around the world, subscribing to a philosophy he called “giving while living.”

Chuck’s story is often told as an extraordinary act of philanthropy. But the idea at its center applies to any family, and it starts with a simple question.

When does wealth make the greatest difference?

Wealth Has a Timing Dimension

While few families will ever match Feeney's scale of giving, any family doing estate planning has the same choice: leave your wealth after you're gone, or share some of it while you're still here to see the impact. That choice is a powerful tool.

Traditional estate planning is built around a future event. Trusts, wills, beneficiary designations, and charitable bequests all help ensure a family's wealth is eventually distributed according to their wishes. These tools answer one question: who will receive it?

Giving while living answers a second question: when? A gift that arrives at the right moment can change the entire direction of a life. The same gift, received decades later, may enhance a life that’s already settled. Timing gives something back to the giver, too. Dollars bestowed to a loved one can fund a moment that matters after you're gone, or while you are there to see it firsthand. That is what the giver receives from giving while living: not just the satisfaction of generosity, but enjoyment of the moment, itself.

Consider a father who leaves a stable job in his forties to start his own consulting practice. A parental financial gift during the months it takes to build a steady client base could be invaluable to him and his dependents. Received ten years earlier, the same money might have gone toward a vacation – enjoyable, but not the life-changing outcome his parents hoped for. Ten years later, the gift could arrive after the business has either succeeded or failed, again missing the opportunity to shape an entire life trajectory. Given at just the right time, however, that gift lets his parents watch what it builds for their next generation.

This approach to gifting is becoming more common as the United States enters what economists call the Great Wealth Transfer, an estimated $124 trillion expected to move between generations over the next two decades. For many families, the question is no longer whether that transfer will happen, but whether part of it might matter more if it happened sooner.

When Life Doesn't Go as Planned

Not every giving moment looks like a milestone worth celebrating. Picture a woman in her late thirties whose marriage ends the same year her younger sister plans a wedding. The family celebrated her once, years ago, with the venue and the toasts. No one throws a party for starting over. What she needs will never appear on a registry: enough for a security deposit on her own apartment and a few months of rent while she finds her footing. The aunt who steps up to write that check could have saved it for her will. The same money would arrive in her niece’s bank account either way, but only one route enables her to watch a child she’s loved for a lifetime stand back up at a low point.

Families who choose to plan for those kinds of years often do so as seriously as they plan for the good ones. These are not moments that show up on a financial planning calendar, but there can be times when a charitable gift can may have a meaningful impact.

A Plan That Changes the Conversation

Giving while living is often framed as a financial strategy. In practice, it usually begins as a family conversation.

Many families spend years discussing investments, tax planning, and estate structures without ever talking about what they actually hope their wealth will accomplish. A grandmother might sit through three meetings about trust structures before mentioning, almost as an aside, that what she really wants most is to see her granddaughter graduate from veterinary school without debt. That single detail can reorganize an entire plan.

The practical details can be handled through trusts and estate plans. The larger conversation is about purpose: what a family wants its wealth to create, and what it would like to witness while there's still time.

For families looking to start that conversation, EP Wealth's Well Said: Giving While Living discussion guide includes questions to help identify and discuss those priorities.

The Fairness Question

These conversations also surface one of the hardest questions in multigenerational planning: how do you give fairly when everyone's life looks different?

Fairness is not the same as equality. Imagine two siblings, a decade apart in age: one has become the default caregiver for their aging mother, coordinating her appointments and medications; the other lives three states away, raising young kids of their own. Treating them identically, dollar for dollar, at the same point in each of their lives, would not feel like fairness to either one. It would feel like a formula standing in for a decision no one wanted to make.

Families who navigate this type of scenario well tend to conclude that the greatest difference comes not from splitting resources identically, but from meeting each person where they actually are.

Funding Opportunity

Education remains one of the clearest examples of how timing shapes a gift's value, regardless of where that education happens to lead.

The average cost of a four-year private college degree now exceeds $260,000* and continues to climb. For family members with the means to help fund education, that support can reach well beyond the classroom. It shapes career choices, financial stability, and even where a young person gets to live: a graduate without loan payments can chase the dream job in the dream city, not just the safest paycheck within commuting distance from home.

The help doesn't have to wait for a diploma, either. For younger children, covering private grade school tuition can provide a step up that might otherwise be out of reach, years before anyone is thinking about college applications.

For a variety of reasons, 529 plans have become a popular vehicle for multigenerational gifting. And the rules have recently gotten friendlier. For years, a grandparent's generosity could quietly shrink a student's financial aid package. That penalty is now gone, so helping with education no longer works against the student.** (Of note: a handful of private colleges still ask about outside support on their own aid forms, so it is worth a conversation with your Advisor before you write the check.)

For a deeper dive into the nuances of passing down wealth via education funding, EP Wealth financial planner Emily Sorensen unpacks the mechanics in this issue's Ask a Planner, from choosing the right vehicle to the surprising flexibility that can accompany it.

Of note, milestones outside the classroom can follow the same giving clock.

Take a first home, for example. A down payment given at age 30 does more than help someone buy a house. It can open the door to decades of potential equity that might not otherwise exist, simply because it arrived with time to work. The same dollars, handed over at 50, might still be generous but wouldn’t do the same job. With an earlier gift, the giver also gets to enjoy breaking bread at the housewarming and beyond, an opportunity not possible with an estate-based gift.

Benefits Beyond Wealth

The mechanics vary by family. Some fund education through 529 plans. Others make annual gifts, fund a milestone purchase, set up a trust, or direct support toward causes and communities their family members care about. The vehicle matters less than the intention behind it: matching resources to the moments that actually need them.

What often surprises families is what these decisions unlock beyond the gift itself. Once the conversation moves past logistics, it tends to turn toward values, responsibility, and the life a family hopes its wealth will help build, one moment at a time.

Feeney chose to give away $8 billion while he was alive to see what it built, rather than leave the accounting to someone else. That is the choice, at any scale: witness the difference your wealth makes, or leave that difference for someone else to discover later.

Not who receives the wealth, but who gets to be there when it matters.

If this is a conversation you want to continue, talk with your Advisor about incorporating giving while living into your overall financial plan, not just your estate plan. EP Wealth is here to help you be there for the moments that matter most to the people you love.

* Source: College Board, Trends in College Pricing and Student Aid 2025.

**The FAFSA Simplification Act removed this penalty beginning with the 2024-25 award year. Source: U.S. Department of Education, Federal Student Aid.

The individuals and families described in this article are hypothetical examples provided for illustration only. Tax provisions described reflect current federal rules, which are subject to change. EP Wealth Advisors does not provide tax or legal advice; please consult your tax and legal professionals regarding your specific situation.