Three generations sit in the same room. They’re all speaking English, but they might as well be using different languages when it comes to money. I see this in almost every family I work with. When wealth grows, the most important conversations become the hardest to have. This is one of the most common challenges I see in multi-generational wealth planning.
The older grandparent who lived through economic uncertainty has fundamentally different values from their young adult grandchild who’s never experienced a major market downturn. Both need to understand each other. Otherwise, family wealth won’t serve its purpose across generations.
The Generational Value Gap
Every family I work with faces this challenge. The older generation built their wealth during times when saving meant survival. They know what it means to go without. The younger generation grew up in times of greater wealth accumulation, with more opportunities to build assets. They’re more comfortable with risk. They’re more optimistic about growth. Neither perspective is wrong. But families need to understand where each generation comes from. Otherwise, they can’t align on what wealth should accomplish.
The key is starting with the “why” behind each generation’s approach. Grandparents aren’t being frugal to be difficult; that’s how they learned to build wealth. Gen Z and millennials aren’t being reckless when they want to invest aggressively. They’re in their prime earning years and have time to recover from market swings.
Getting Everyone on the Same Page
The biggest mistake I see families make is avoiding these conversations altogether. Money discussions feel taboo, so families put them off until it’s too late — often until after someone has passed away and emotions are running high.
I learned this lesson personally when my father was dying of cancer. For years, he kept me informed about his retirement plans. He shared his vision for my daughter’s future. But in his final months, everything changed. My stepmother had the estate attorney come to their house on a Saturday. She convinced my father to change his entire estate plan. Because those conversations had happened privately, the rest of the family was blindsided.
That experience taught me why it’s necessary to bring families together for these discussions while everyone’s still healthy and thinking clearly. This can help reduce the likelihood of surprises that tear families apart later.
The Right Time for Different Conversations
I don’t recommend putting young adults in family wealth meetings too early. A 21-year-old isn’t ready for the full picture. They’re still figuring out their career and their own financial foundation. But someone in their 40s? They’re in their peak earning years, juggling private school tuition and thinking about retirement. They’re ready to understand the bigger picture.
When I work with families, I usually meet with different generations separately first. With younger family members, we focus on building their own financial foundation, like emergency savings, debt management, and long-term planning. With older generations, we’re often discussing legacy planning, tax strategies, and how to structure inheritances responsibly.
The magic happens when we bring everyone together. They realize they’re all working toward the same fundamental goals, just from different starting points.
Setting Boundaries and Managing Expectations
One of the hardest conversations involves setting boundaries around financial support. Younger family members sometimes assume inheritance is automatic, especially when they’ve grown up with wealth. They think, “My friends are inheriting from their grandparents, so I will too.”
But here’s what they need to understand: significant wealth comes with structure. Your parents and grandparents likely set up trusts with specific rules. You’re not getting a lump sum to spend however you want. There are guidelines, expectations, and often requirements about work, education, or life milestones.
I’ve had to explain to more than one young adult: “Don’t plan to work at Chick-fil-A and live with your parents until you’re 40, assuming you’ll inherit enough to coast through life.” The wealth creators in the family didn’t build that wealth by avoiding responsibility. They don’t want future generations to either.
When Family Business Succession Planning Complicates Things
Family businesses add another layer of complexity. I see this pattern repeatedly: the grandparents start the business and the parents grow it. Then the third generation comes around. Maybe two kids want to be involved, and the third wants nothing to do with it.
That’s natural, each generation has different aspirations. But it requires careful planning to ensure fairness. The kids who stay in the business might receive ownership through partnerships and gifting strategies, while the one who pursues other interests needs to be compensated fairly through other family assets.
These conversations are important. They allow everyone to be aligned on expectations and ensure fairness for all family members.
The Cost of Secrecy
I once worked with a family where the parents died within three months of each other. This happened during a year when there was no federal estate tax. Five sisters suddenly inherited significant wealth, but they had strained relationships and didn’t trust each other. One sister was appointed executor, and the family meetings became so contentious that the estate attorney and I had to start video recording sessions to protect everyone involved.
The biggest friction point? One sister didn’t have children, so she felt it was unfair that a separate trust was designated for the 12 grandchildren. The parents had structured their estate based on their values. They wanted to provide for the next generation, but because those conversations hadn’t happened openly, it felt like a betrayal to the childless daughter.
We eventually worked through it, but it took months of difficult meetings that nearly destroyed what was left of the family relationships.
Building Trust Through Transparency
The families that navigate multi-generational wealth transfer most successfully are the ones that prioritize ongoing communication. I recommend annual family meetings for high-net-worth families to bring together all the key professionals, financial advisor, CPA, estate attorney, etc. There are so many moving parts. This coordinated approach to complex wealth management can help prevent details from falling through the cracks.
These meetings help ensure everyone understands the family’s values, knows what to expect, and feels heard in the process.
Trust and openness. That’s what you need to make family wealth work across generations. When family members feel surprised or excluded, that’s when relationships fracture and wealth becomes a source of conflict rather than opportunity.
My Process for Family Alignment
When I work with families navigating these challenges, here’s how we approach it together:
- Start with separate conversations.
I meet with different generations individually first to understand each perspective and address age-appropriate concerns.
- Explore the “why” behind each approach.
Help everyone understand what drives their generation’s relationship with money and risk.
- Set clear, realistic expectations.
Explain what wealth transfer actually looks like, including trust structures and responsibility requirements.
- Coordinate the moving parts.
Bring together all the key professionals and facilitate family meetings where everyone can communicate effectively.
- Act as translator and mediator.
Bridge generational gaps and help families realize they’re working toward the same fundamental goals from different starting points.
The magic happens when families move from speaking different languages about money to having aligned conversations about their shared future.
Moving Forward Together
Navigating family wealth isn’t about having perfect conversations or avoiding all conflict; it’s about creating a framework where different generations can understand each other’s perspectives and work together toward shared goals.
Every family’s situation is unique, but the principles remain the same. Start conversations early, be transparent about expectations, respect generational differences, and prioritize relationships over transactions.
The families that get this right often strengthen family bonds and create legacies that serve multiple generations.
Take Control of the Vision You’ve Built
Wealth should create freedom, not more complexity. If you’re interested in exploring how your financial picture supports your legacy goals, we invite you to a Wealth Architecture Blueprint meeting.
In this focused session, we’ll discuss your priorities and balance sheet, identify blind spots or inefficiencies, and map out where more structure or coordination could better serve your goals, today and across generations.
You’ll walk away with a clearer picture of what’s working, what needs attention, and what steps to take next.
Contact us to schedule your session.
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Shelly Baker is a Memphis-based wealth strategist focusing on high-net-worth family planning at Waddell & Associates.
This content is for informational purposes only and should not be considered legal, tax, or investment advice. Opinions are those of the author and may change. Waddell & Associates is an SEC-registered investment adviser. Registration does not imply a certain level of skill. Past performance is not indicative of future results. Please consult your professional advisors before making financial decisions.
