‘Are we rich?’ The question billionaire and millionaire parents dread, and what happens when they dodge it

There’s a question wealthy parents dread, and it’s not coming from activists asking them about their tax returns.

Jessica McGawley, a consultant who’s worked with high-net-worth families for nearly two decades, told Fortune that she has to explain to clients that their children are not “being greedy or rude” by suddenly asking “Are we rich?” after noticing their family has more than one house.

“How a parent feels comfortable talking about sex and death is also how they feel comfortable with money,” she said.

As the scions of wealthy families anticipate the $124 trillion Great Wealth Transfer —the sum Cerulli Associates projects will change hands in the U.S. through 2048—they’re often unprepared to handle their inheritance because their families haven’t talked with them about money and how to manage it.

McGawley founded her firm Dallington to address this issue, based on her experience of parents having put together “a watertight paper document that explains everything” but failing to actually talk through it with their kids.

“Successful families are very good at preparing wealth for the children.

They are not good at preparing the children for the wealth,” McGawley said.

“So if you spend all this time and all this energy preparing your wealth for your children, but don’t prepare them for what they’re receiving and why, you’ve missed the point.” A Fidelity study last year found the majority of parents age 55 or older with at least $500,000 in investable assets haven’t talked to their kids about inheriting money, with more than half (52%) reporting they haven’t communicated their net worth and 68% reporting they haven’t told their kids what they’ll inherit or if they’ll inherit at all.

About a third (35%) said they don’t want their children to know how much they’ll get.

But parents who share completed plans with their kids are more than three times as likely to feel confident in their planning, Fidelity separately found in a 2026 survey of 654 married or partnered adults age 55 or older with a net worth of at least $500,000 and at least one adult child.

But only 21% have communicated a completed estate plan to their adult children.

Reasons why they don’t McGawley has worked with more than 150 ultra high net worth individuals, with most of her clients falling into the centimillionaire bucket.

She said mostparents worry that letting their kids know the extent of their wealth will make them entitled.

“There’s this fear that if your kids know how much money that you have as a family, that they’re going to basically give up studying, give up motivation, won’t be bothered—basically have a meal ticket for the rest of their life,” she said.