Providing children with a high standard of living inadvertently sets that lifestyle as their baseline expectation. This becomes a curse, as they may feel like a failure if they can't replicate it or be prevented from pursuing a fulfilling but less lucrative career.

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Even after achieving massive success, Chris Appleton experiences guilt and second-guesses purchases, a residual effect of his impoverished childhood. This "poor boy inside" demonstrates that deep-seated financial trauma often persists and isn't automatically cured by accumulating wealth.

Be very careful who you socialize with, as they will set your baseline expectations for a "normal" life. It's much easier to be content when your reference group has a similar lifestyle. Constant exposure to people with dramatically higher wealth makes lifestyle inflation and discontent almost inevitable.

Wealthy parents who endlessly provide for their adult children may inadvertently signal a lack of faith in their abilities. This can lead to depression and a sense of incapability, as the financial support is perceived as a message that they are seen as losers.

Massive wealth imposes a hidden 'social debt'—a crushing weight of expectations that dictates how heirs must live, who they can marry, and what values they must hold. As the Vanderbilt family story shows, this can destroy independence and happiness, effectively making heirs prisoners of their fortune.

Contrary to popular belief, a large income doesn't guarantee wealth. High earners are more susceptible to "competing with the Joneses," leading to lifestyle inflation that consumes their income. People earning less may face less social pressure, making it easier to save and invest.

Kara Swisher explains that despite growing up with money, her mother's excessive spending and resulting financial instability made her frugal. This experience instilled a deep-seated need for financial control and a desire to always 'have enough,' demonstrating how childhood financial trauma can shape habits regardless of actual wealth.

While well-intentioned, providing prolonged financial support to adult children communicates a belief that they are incapable of succeeding on their own. This cripples their self-esteem and ambition, making the enabling parent the root of the problem.

Each generation should strive to give their children a better life, which will inevitably appear "spoiled" by previous standards. The parent who struggled feels their child must also struggle, forgetting their own life seems luxurious to their grandparents. This is progress, not a moral failing.

When self-worth is tied to constant success (e.g., getting straight A's), failure becomes emotionally devastating. As an adult, this can translate into avoiding risks altogether, because the potential psychological pain of failing outweighs the potential rewards of a bold venture.

Prosperity subtly ingrains lifestyle habits that become part of your identity. As industrialist Harvey Firestone noted, trying to return to a simpler life later is nearly impossible, as you would feel like a "broken man" for failing to maintain the standard you've become accustomed to.