As we approach the holiday season, many families will find themselves gathered around the same table — sometimes with several generations together in one place. Grandparents, parents, adult children, and grandchildren may share memories and family history, but their experiences with money can be remarkably different.
One generation remembers when saving meant putting money in a passbook account and buying a home was considered the cornerstone of financial security. Another came of age during periods of high inflation and interest rates. Their children may have entered adulthood during the Great Recession. And the youngest adults have experienced a pandemic, rapid inflation, expensive housing, digital investing, social media, and a world where nearly every financial decision can be made from a phone.¹
All those experiences matter.
The way we think about money isn't formed in a vacuum. It is influenced by the economy we grew up in, what our parents taught — or didn't teach — us, the financial setbacks we've experienced, and what we've watched happen to the people around us.
Put four generations around a Thanksgiving table, and you may get four very different definitions of what it means to be financially free.
The Same Dollar Doesn't Mean the Same Thing to Everyone
Imagine a grandparent who grew up hearing stories about the Great Depression or was raised by parents who lived through it. Saving may represent financial freedom. Debt may feel inherently dangerous. Throwing something away when it can still be repaired might seem almost unthinkable.
Their children may have a different relationship with money. They may have spent decades focused on buying a home, building a career, putting children through college, and accumulating enough to retire comfortably. To them, financial freedom may mean independence: owning their home, having a healthy retirement account, and not needing financial help from their children.
Move another generation down the table and priorities can change again.
Many Millennials entered adulthood around the Great Recession and have since navigated student debt, housing challenges, and a changing economic landscape. Research comparing Millennials with previous generations at similar ages found that Millennials were more likely to carry student debt and tended to owe more when they did.²
Then there is the youngest adult generation, which has grown up with financial information, and misinformation, available constantly. Investing can mean a workplace retirement plan, but it can also mean an app, cryptocurrency, an online personality discussing stocks, or a viral video promising a new path to financial independence. FINRA research published in 2025 found that investors under age 30 were substantially more likely than those 65 and older to report relying on social media for financial information.³
None of these perspectives is automatically right or wrong. They are often responses to very different circumstances — and that's exactly why conversations about family wealth can become complicated.
"When I Was Your Age..." Only Tells Part of the Story
It’s natural to look at financial decisions through the lens of our own experiences — especially when comparing where we are today with where we were at someone else’s age.
A parent who bought a first home decades ago may have difficulty understanding why an adult child earning what sounds like a very good salary is struggling to buy today. A child may wonder why a retired parent with substantial savings remains reluctant to spend any of it. A grandparent may not understand why a younger relative would willingly change jobs every few years instead of valuing stability.
From each person's perspective, their reasoning may be perfectly logical.
And today's numbers help illustrate why comparisons across generations aren't always straightforward. According to the Federal Reserve's latest Survey of Household Economics and Decision-making, younger adults continue to face distinct financial pressures. In 2025, 49% of adults under age 30 lived with a parent, and 47% of adults ages 18 to 29 received help from someone outside their household to cover at least one expense during the prior year.
The problem comes when we assume that what worked for one generation should work exactly the same way for the next.
Good financial planning requires context. Income matters, but so do housing costs. Investment returns matter, but so does time horizon. Saving matters, but so does what you're saving for. And a strategy that made sense at age 35 may look completely different at 65 or 85.
Sometimes understanding another generation's financial choices starts with replacing "Here's what I did" with "Help me understand how you're thinking about it."
When Different Money Values Become Family Decisions
Generational differences become particularly important when money stops being an individual decision and becomes a family one.
Consider a parent or grandparent who wants to help an adult child purchase a home. Is providing a down payment a thoughtful use of family wealth, or does it prevent the child from learning financial independence?
There isn’t one universal answer, as every family has its own dynamics and each individual brings their own personal values and priorities to the decision.
The same issue can arise with paying for grandchildren's education, helping adult children with recurring expenses, making lifetime gifts, providing care for aging parents, leaving an inheritance, or deciding what happens to a family business or vacation property.
One generation may view an inheritance as money that should be preserved and passed down again. Another may see it as an opportunity to buy a home, start a company, travel, or retire earlier.
Multigenerational planning can involve a wide range of circumstances that are unique to each family. Past financial support, caregiving responsibilities, individual financial situations, and the needs of future generations may all be part of the broader picture. Should every child inherit exactly the same amount? What if one child has already received substantial financial help? What if another spent years caring for an aging parent? What if one child is financially successful while another faces greater financial challenges? How should grandchildren or other generations factor into the plan?
These aren’t simply investment or tax questions. They reflect the many personal, financial, and family considerations that can shape a long-term plan.
Wealth Transfer Is About More Than Transferring Assets
Families often spend years planning how assets will eventually move from one generation to another.
But there is another kind of transfer happening long before an inheritance ever arrives.
Families transfer attitudes about money.
Growing up, children notice whether their parents talk openly about finances or avoid the subject. They see whether money is treated primarily as a source of security, opportunity, status, generosity, or stress. They absorb messages about debt, investing, spending, work, and what it means to have "enough."
Sometimes those lessons are intentional. Often, they aren't.
That is one reason multigenerational financial planning shouldn't begin and end with estate documents. Wills, trusts, beneficiary designations, and powers of attorney can establish what happens to assets. They cannot, by themselves, explain the thinking behind those decisions.
For families hoping to build a legacy, the "why" can be just as important as the "what."
You Don't Have to Agree About Money to Understand Each Other
Even though financial priorities can look very different from one generation to the next, those differences don’t necessarily need to be resolved or reconciled — they can simply reflect the different circumstances, experiences, and stages of life that shape each person’s perspective.
Understanding those differences doesn't require everyone to reach the same conclusions.
Parents can explain why financial independence matters to them while recognizing that their children's economic reality may be different from their own. Adult children can understand why parents who spent decades accumulating wealth may find it emotionally difficult to start spending it. Grandparents can share the experiences that shaped their financial habits without assuming those habits must be replicated exactly.
These conversations can also reveal where a financial plan and a family's expectations aren't quite aligned.
Perhaps parents intend to leave the family vacation home to three children, while none of the children actually wants it. Maybe grandparents have been diligently funding education accounts without realizing their family has different plans. Perhaps adult children assume there will be an inheritance that their parents intend to give to charity.
Those are useful things to discover while everyone still has the opportunity to talk about them.
Four Generations, One Family Plan
A strong multigenerational financial plan doesn't require everyone in the family to think about money the same way.
What matters is creating enough communication that the differences aren't discovered for the first time during a crisis, after someone's death, or when a major financial decision has already been made.
For families with significant or complex wealth, that can mean going beyond the traditional relationship between one client and one financial advisor. Adult children may need financial education. Aging parents may need additional support. Business owners may need to coordinate succession with family members who have very different visions for the company's future. Estate strategies may need to balance tax considerations with complicated family dynamics.
This Thanksgiving, you don't necessarily need to turn dinner into a family financial meeting.
But listen closely.
The stories your family tells about work, homes, spending, saving, success, and the future may tell you quite a bit about what money means to each individual.
And understanding that may be one of the most valuable things you pass around the table.
Sources
Board of Governors of the Federal Reserve System, Economic Well-Being of U.S. Households in 2025, May 2026.
- Pew Research Center, Millennial Life: How Young Adulthood Today Compares With Prior Generations, February 14, 2019.
FINRA, Social Media-Influenced Investing, December 2025.