“Shirtsleeves to shirtsleeves in three generations” is an old proverb that describes a common trend in wealth building. The first generation starts with little and builds wealth. The second generation may preserve it, but will rarely grow it. And the third generation blows it.
Like many common sayings, this one is grounded in reality. Research has shown that around 70% of affluent families see wealth erosion by the second generation and 90% can’t maintain their wealth by the third generation.
Understandably, many people who have acquired money or property want to stop that from happening in their family. But is this doable, and how can they make it happen?
Thanks for subscribing!
Take control — get our free newsletter.
By signing up, you accept Moneywise Terms of Use, Subscription Agreement, and Privacy Policy.
Let’s pretend that Sara is very wealthy and wants to leave well over $1 million to each of her three grandkids, Daniel, Tegan, and Eddie. However, Sara doesn’t just want to hand over this money. She wants them to pass a rigorous financial literacy test first. But can she make it happen? Is it fair to expect this, and is this the best way to protect her funds?
Sara can require a financial literacy test, but things may get complicated
First things first: Sara is not the only one with these concerns, and she absolutely has the right to require that her grandkids pass a financial literacy test. She also has tools she can use to make this a condition of Daniel, Tegan, and Eddie receiving their inheritance.
“This grandmother is trying to accomplish something that is very common: Generational asset protection,” Trish Yeatts Butcher, Esq, an estate planning attorney and owner of Arch Legacy Firm, told Moneywise. “As part of the ‘great wealth transfer,‘ we’re seeing more and more families interested in ensuring their children do not squander their inheritance.”
Yeatts Butcher acknowledged that while requiring a financial literacy test isn’t something everyone does, “we definitely see this pop up fairly often, especially with beneficiaries who have a history of financial mismanagement or a drug or alcohol dependency.”
If this is something Sara wants, she can make it happen, but it may be complicated.
“You leave the inheritance to a trust, and then bake in your requirements to the trust,” Kelsey Simasko, attorney at Simasko Law, told Moneywise. “From there, it is up to your trustee to administer the ‘test’ and determine if the beneficiary passed it.”
Unfortunately, as Simasko explained, “the test scenario is ripe for fighting. If the trustee says the beneficiary did not pass the test, but the beneficiary believes they passed, the beneficiary will bring the case into court, and the judge will have to determine if the beneficiary should get the money.”
Simasko warned this could become “very expensive, very fast” and that while Sara may have “baked in the financial literacy test to protect the money, now all the money is being spent on legal fees to decide if the beneficiary actually passed the test.”
Passing a test also doesn’t mean the grandkids will follow best practices. Plenty of people intellectually understand what they should do with their money, but they don’t necessarily do it.
Must Read
- The ultra-rich use these 5 real estate strategies to build wealth while they sleep — you can start with just $100
- Here’s the average income of Americans by age in 2026. Are you keeping up or falling behind?
- Insurance companies profit most from drivers who auto-renew without shopping around. Comparing 100+ quotes takes 2 minutes and costs nothing
Join 250,000+ readers and get Moneywise’s best stories and exclusive interviews first — clear insights curated and delivered weekly. Subscribe now.
There may be better ways to preserve her wealth
Rather than trying to impose a test on her grandkids, Sara might be better off structuring her estate differently to help ensure that each grandchild can be truly supported by the inherited funds for a long time.
“Usually, instead of a test, it is an age. For example, they get all the money when they turn 25, or they get half of the money at 25 and the other half at 35. With the age requirement, there is less room for fighting, but the beneficiaries will get the money when they turn that age regardless of how responsible they are,” Simasko told Moneywise.
Simasko also said that Sara could put the funds in a discretionary trust, which allows the trustee discretion about when to provide distributions for things like health, education, and support. The trustee could pay the bills directly for certain approved costs, or provide a small amount of money each year and increase it as the grandkids show they’re responsible.
“Families are moving beyond simple age-based distributions toward education requirements, mentorship components, and even family governance structures that prepare heirs well before they ever receive a check.” Lisa McCurdy, founder of The Wealth Counselor, LLC and of Defining Legacy Group, told Moneywise.
It’s worth exploring these options, which could provide much stronger protection for inherited assets and hopefully help the grandkids assume responsibility for the gift they’ve been given. Sara’s grandkids could benefit from plans like these, so when they receive an inheritance, they can truly make the most of it.
You May Also Like
- JP Morgan sees gold hitting $6,000/oz before 2027 — and a Gold IRA lets you hold the physical metal while deferring the tax bill. Get your free guide from Priority Gold
- Dave Ramsey warns nearly 50% of Americans are making 1 big Social Security mistake — here’s what it is and the simple steps to fix it ASAP
- Thanks to Jeff Bezos, you can now become a landlord for as little as $100 — and no, you don't have to deal with tenants or fix freezers. Here's how
- Millionaires under 43 are reshaping investing — just 25% of their portfolios are in stocks. Here’s where their money is going
Christy Bieber has 15 years of experience as a personal finance and legal writer. She has written for many publications including Forbes, Kilplinger, CNN, WSJ, Credit Karma, Insurify and more.
