After selling a company or receiving a massive windfall, most centimillionaires—those with over $100 million in assets—make at least one financial mistake they later wish they could undo. Many of these regrets involve decisions that directly affected their children and how the next generation views money, property, and long-term wealth.
The biggest financial regrets among centimillionaires aren’t about losses—they’re about the wealth lessons accidentally taught to their children.
One common mistake involves buying dream homes immediately after a liquidity event. Parents excitedly purchase massive properties to give their families the perfect lifestyle, only to discover something surprising. Within 12 to 24 months, that dream house loses its appeal as family priorities shift. Children outgrow spaces, commutes become burdensome, and what seemed perfect suddenly feels like a burden. These single-family homes often take 8 to 12 years to sell, frequently at prices lower than what was originally paid. Many now recommend renting first to avoid locking into poor long-term housing decisions and to give families time to learn their true needs.
The real damage goes beyond money. Children observe their parents making emotional purchases during moments of excitement, learning that wealth means buying whatever feels good in the moment. This lesson creates problematic spending patterns that follow kids into adulthood.
How did centimillionaires fix this mistake? Many shifted their approach entirely. Instead of rushing into real estate purchases, they waited. They rented first, giving families time to understand what they actually needed versus what sounded exciting. This patience taught children that thoughtful decision-making matters more than immediate gratification.
Another widespread regret involves overpaying for wealth management services that essentially provided basic strategies. Parents paid 60 basis points for services they could have obtained for 10 basis points elsewhere, simply because they didn’t understand fee structures. Their children noticed this financial carelessness and assumed that wealthy people don’t need to worry about costs.
Centimillionaires corrected this by becoming transparent with older children about fee optimization and value assessment. They explained how institutional alternatives work and why understanding true costs matters regardless of wealth level. This transformed a mistake into a teaching opportunity about financial efficiency. Some families instituted regular family meetings to review assets, trusts, and long-term wealth preservation strategies together.
The pattern is clear. The wealthiest individuals don’t regret honest investment losses nearly as much as they regret the unintended lessons their rushed decisions taught their children about money, patience, and value.
