Giving Now Versus Leaving Later: Rethinking How You Pass Wealth to the Next Generation

For many families, the default plan is simple and has remained unchanged for decades: build wealth over a lifetime of hard work and discipline and pass what’s left to children and grandchildren as an inheritance. Until more recently, it’s been a tradition steeped in assumption than intentional design in many cases. And while there’s nothing wrong with that approach, a growing number of families are starting to ask themselves if there is a better way to do it.

It’s estimated that $80 trillion to $125 trillion will pass from Baby Boomers and the Silent Generation to Gen X, Millennials, and Gen Z by the year 2048. With talks of this “Great Wealth Transfer” growing larger and larger, it’s a consideration that many families are starting to make, and it’s a question that we’re beginning to be asked more and more: Is there a better time to give than when I pass away?

The part of that long-standing tradition of gifting through inheritance that can sometimes go unexamined is when that wealth will actually be received, and whether that timing aligns with when it could make the greatest impact. As it does with many things, the decision of when to give comes down to a person-by-person and couple-by-couple basis and what makes sense for you. 

In this article, we want to share the stories of two families, John and Lisa Harlow and David and Karen Poole, and how different approaches achieve different goals, but end in the same multigenerational impact. The names and scenarios in this article are fictional and used for demonstrative purposes only.

John and Lisa Harlow: The Early Givers

John and Lisa are in their early 60s. They both had long, successful careers and after decades of disciplined saving, they’ve accumulated roughly $5 million across their retirement accounts, brokerage assets, and cash savings. Their plan already supports their lifestyle, even with conservative assumptions. Their three children, ages 27, 31, and 33, are all in what you might consider financial turning points phase of life:

• Their oldest daughter Abby and her husband have the opportunity to purchase a home in a great school district, but they’re coming up short on the down payment and facing either a much smaller home or years of delay.
• Their middle child, Hope, has a chance to step back from a demanding job to spend more time with young kids, but it only works if they can eliminate a chunk of existing debt and build a safety net.
• Their youngest, Carson, has been offered a job with significant long-term income potential, but it requires stepping away from work for several months to complete a certification program, something he couldn’t do without a financial cushion to cover living expenses during the transition. 

John and Lisa began asking a different question: What would happen if we stepped in right now, at this exact moment? 

After working with their financial advisor and CPA through a plan to ensure their own long-term security, they decide to gift $80,000 to each child. Here’s what that looked like in practice:

• Abby and her husband weren’t only able to buy the home in the better school district, they avoided PMI and dropped their monthly payment enough for Abby to begin working part-time and pick the kids up from school every day.
• Hope was able to pay off her lingering student loans, fully fund their emergency fund, and create the margin to shift to a more flexible role during a season that matters most at home.
• Carson was able to step away from work and complete his 10-week certification course without taking on any debt. He’s now making more than John or Lisa ever have before. 

With these gifts, John and Lisa created clear ripple effects:

• Each child avoided a decision that would have created long-term financial drag (a home that’s too small, career burnout, or high-interest debt).
• Opportunities that were previously just out of reach became achievable.
• The next generation, their grandchildren, benefit indirectly through more stable homes, present parents, and stronger financial footing.

Most importantly to John and Lisa, however, was the gift they received in getting to watch their kids get a foot up in life and open doors that they would have never had the opportunity to even approach without their parents’ generosity.

David and Karen Poole: The Legacy Builders

David and Karen, also in their early 60s, find themselves in a very similar financial position – about $5 million in total assets, no debt, and a solid retirement outlook. Their philosophy, however, is different. They value flexibility and security above all else. They’ve seen healthcare costs impact family members and want to ensure they never become a burden to their children. They also believe there is value in allowing wealth to compound over time.

So instead of making large lifetime gifts, they focus on:

• Continuing to invest during the early years of retirement.
• Maintaining a healthy margin for unexpected expenses.
• Keeping their long-term estate plan intact.

They still help their children in smaller ways (occasional gifts, covering family trips, and contributing modestly to grandkids’ education) but they intentionally avoid large cash transfers. Over the next 20-30 years, their portfolio continues to grow, even as they take distributions. By the end of their lives, the estate has grown to close to $8 million.

Their children, now in their late 50s and early 60s, receive a significantly larger inheritance than they would have decades earlier. The impact shows up differently:

• Their children are able to secure their own retirement, eliminating any lingering uncertainty.
• They increase charitable giving in a meaningful way.
• They begin transferring wealth to the next generation - funding education, helping with home purchases, and creating opportunities for their own children.

In this case, the wealth wasn’t used to relieve early-life pressure; it became a tool for legacy expansion across multiple generations.

What These Stories Show

Both families were thoughtful. Both made intentional decisions. Both create real, lasting impact. The difference wasn’t in discipline or success, it was simply in what they prioritized:

• John and Lisa prioritized timing, visibility, and early-life impact.
• David and Karen prioritized growth, security, and long-term maximization. 

Importantly though, neither outcome is "better." They simply reflect different values.

The Real Question

This isn’t just a financial decision; it’s also a philosophical one.

Do you want to help solve problems while they’re happening, or create the largest possible pool of assets for future use? Do you value seeing the impact firsthand, or maximizing what’s ultimately passed down?

For many families, the right answer is a blend of both. But the most important step is to move from an assumed plan to an intentional one because either path, when done thoughtfully, can shape your family for generations.