The client had planned the weekend for four months. A rented lake house. Eight people, his extended family. He paid for everything, which had been the point. What he had not planned on was the Monday morning call to his financial advisor, asking, essentially, whether he was being unreasonable.
Thomas Staley has taken some version of that call for close to twenty years. A CERTIFIED FINANCIAL PLANNER™ at Maia Wealth, he works with clients who have spent long careers building enough financial security to start giving it away, and who then discover that the act of giving turns out to be more complicated than they anticipated. His clients are not struggling with how to be generous. They are struggling with what happens after.
“The industry barely talks about this,” Staley said in a recent conversation. “We talk about gifting strategies, we talk about tax efficiency, we talk about trust structures. We almost never talk about why a client who just spent $15,000 on a family vacation is sitting in my office the following Monday feeling taken advantage of.”
The broader financial planning world has begun to acknowledge, at least around the edges, that family wealth conversations are harder than the technical literature suggests. A 2024 study from Edward Jones, conducted with Morning Consult and NEXT360 Partners, found that while 61 percent of inheritance recipients felt gratitude, only 25 percent felt prepared for what they were receiving. The same study found that two-thirds of givers plan to leave instructions for their heirs, but far fewer have actually discussed those instructions with the people who will receive them. Joe Coughlin, the MIT-based researcher who advised on the study, put it bluntly at the time: the talk has to happen before the transfer.
The backdrop to all of this is the scale of what is coming. Cerulli Associates projects that more than $84 trillion will pass to heirs and charities through 2045, the largest intergenerational wealth transfer in American history. The technical side of that transfer, trusts, exemptions, tax structures, has been well-studied. The human side, Staley argues, has not.
Staley’s argument is a variation of the same point, applied earlier in the cycle. Long before a formal wealth transfer, families run a constant low-grade version of the same dynamic every time the wealthier member picks up a check.
“People assume the problem is the cost, or the difficult relative, or some dynamic they cannot control. It is almost always the conversation they did not have before the trip. They tried to avoid awkwardness by staying vague, and that is precisely what created the awkwardness.” – Thomas Staley, Maia Wealth
The conversation hosts keep skipping
The advice Staley gives is direct. Before anyone books a flight, the host needs to call the group and name the trip. If the weekend is a gift, the host should say so plainly. If the host is covering the house and dinners but expects guests to handle their own travel, that also needs to be spelled out, specifically, before anyone books a ticket they later feel strange about.
Clients resist this more than it would seem they should. They do not want to sound as though they are announcing their wealth. They do not want to make the money part of the trip feel heavy. So they stay vague and hope their guests will fill in the blanks correctly, which guests almost never do.
The irony Staley points to is that guests without clear expectations are the ones whose behavior ends up feeling strangest. A guest uncertain whether she owes for dinner will reach for her wallet at every check. A guest unsure whether a contribution is expected will spend the weekend quietly tallying what the experience must be costing. Remove the uncertainty and most of those moments disappear with it.
Ninety seconds of conversation, Staley argues, would prevent the majority of what ends up on his Monday call. Most hosts never have it.
Where Staley parts ways with the industry
This is the point at which Staley diverges from what much of the wealth management industry tells clients. The prevailing advice, particularly around intergenerational wealth and gifting, emphasizes long-term planning frameworks, trust structures, and tax efficiency as the starting points for family generosity.
Staley considers that sequence backwards.
“The industry has it in the wrong order,” he said. “Planners want to talk about the structure before the family has figured out the feeling. But the structure does not work if the feeling is wrong. I have watched families execute technically perfect gifting strategies and generate real resentment anyway, because the emotional layer underneath was never sorted out.”
That critique is not universally shared. Many advisors would argue the opposite, that technical planning creates the clarity families need to have the harder conversations. Staley does not entirely disagree. His position is narrower: the technical work cannot substitute for the emotional work, and most advisors, in his view, are happier to do the former than the latter.
Sharing versus subsidizing
A second pattern shows up differently. Clients who have been generous for years, rarely through a single conspicuous gift, but through smaller gestures that quietly accumulated. The sibling who helped with rent during a difficult stretch that turned into three years. The parent covering grandchildren’s activities because no one else will. The adult who is always the one to grab the check.
Staley draws a distinction between what he calls sharing and subsidizing. Sharing takes the shape of a trip, a milestone celebration, a specific occasion. It concludes. Subsidizing is open-ended, and open-ended financial support inside families tends to calcify into a role. The sibling who has been the bank for fifteen years finds it difficult to stop being the bank. The adult child accustomed to a steady safety net experiences its withdrawal as abandonment, even when the parent is simply retiring.
This is also, Staley noted, where the industry trend toward what researchers call “giving while living,” the shift away from traditional inheritance toward real-time support for adult children and grandchildren, can go wrong if families are not careful. The Edward Jones study found that giving while living is becoming more common, particularly among families buying experiences or funding education. Staley thinks the trend is healthy in principle. In practice, he said, it often replicates the subsidizing pattern on a larger scale.
“The families I have watched do this well for twenty years are not using sophisticated gifting strategies. They are simply clear with themselves about why they are giving, clear with the recipient about what the gift is, and willing to let it go.” – Thomas Staley, Maia Wealth
The half-life of gratitude
Staley points to another pattern most hosts misread. The first trip a client takes a sibling or close friend on produces visible gratitude. The third trip still generates real appreciation. By the sixth or seventh year of what has become an annual tradition, the gratitude has flattened. Not disappeared. Flattened. The trip has become the expected baseline.
Clients often interpret this shift as rudeness. Staley sees it differently. People adjust to their circumstances, and that adjustment includes circumstances other people have created for them. A family flown somewhere warm every December for five consecutive years will plan their sixth year around the trip. That is not entitlement. It is ordinary human calibration.
What matters, in his view, is whether the host still wants to keep generating that expectation. Some do. Others realize, somewhere around year seven, that what began as a gesture has quietly become an obligation they now carry alone. Either outcome is acceptable, he said. The host simply needs to know which one is occurring.
If you cannot give it cleanly, give less
The line Staley returns to with clients, the one that tends to stick, concerns whether a gift can be given cleanly. By clean he means given without any internal ledger, any expectation of future behavior, any silent scorecard the host is maintaining. If the host is likely to remember the cost of the trip three years later during an unrelated argument, the trip was not given cleanly.
When clients recognize they cannot give something cleanly, Staley advises them to scale the gift down rather than deliver it with hidden strings. A smaller trip the host can fully release is worth more than a lavish one the host is still tracking. A single covered dinner given freely is worth more than a covered week delivered with resentment underneath. The cleanness of the gift, in Staley’s experience, matters far more than its size.
Where planning comes in
The technical questions do eventually arrive. Annual gift exclusion limits. Lifetime exemption. Whether a trust structure is appropriate for a specific family goal. Clients of Thomas Staley Maia Wealth invest meaningful time in those mechanics, and Staley considers them important.
He is particular, however, about the sequence. The mechanics only function properly once the family has resolved the softer questions underlying them. Why are we giving? to whom? What do we want the arrangement to feel like five years from now? Families that answer those questions first can implement almost any gifting structure effectively. Families that skip them, he said, end up with tax-INefficient gifts that still generate resentment, which is the worst of both outcomes.
That philosophy is the one around which Staley built his practice at Maia Wealth. He calls it planning-first. What he means is that the kitchen-table conversation needs to precede the portfolio conversation, and that most of the job of a CFP, at least as he practices it, is helping clients get the sequence right.
For clients who do, Staley said, the technical work becomes straightforward. For clients who do not, no amount of structural optimization fixes what is happening on Monday morning.
About the Source
Thomas Staley, CFP®, MBA, is a financial planner at Maia Wealth. He has twenty years in financial services, earned his undergraduate degree in Finance and his MBA from Ball State University, and received his CERTIFIED FINANCIAL PLANNER™ designation in 2011. Staley works with high-earning families on a planning-first approach that integrates investments, employer benefits, estate questions, and the human dynamics money creates inside households. Learn more at tomstaley.coor visit the Maia Wealth team page at maiawealth.com/team.