How much is too much?

It’s the ultimate Goldilocks dilemma: If you leave too much wealth to your children, there’s the risk of entitlement, dependency and demotivation. If you leave too little, you fear it will lead to resentment, financial insecurity and discord within the family. So, how much wealth to pass down is just right?

This dilemma is becoming more common as baby boomers age and wealth transfers accelerate. With more liquidity events—such as business sales—happening, finding the right amount to leave to the next generation is top of mind for many families.

At the heart of the question is a twin desire that most parents share: to see their children succeed and to protect them from financial hardship. But this often collides with the goal of fostering independence, motivation and responsibility. Judging by the rising wave of wealth transfers—and the growing number of Family Office clients seeking guidance on that Goldilocks sweet spot—this dilemma is only intensifying.

Families focused on “how much?” are asking the wrong question. The real issue isn’t about the numbers—it's about the readiness.

As an avid cyclist and runner, I can offer a comparison. Let’s say you’re preparing for a marathon or long-distance cycling race. Without proper preparation—nutrition, rest and a solid training plan—you’re setting yourself up for failure (ask my younger, newbie self about the consequences of running a half marathon without adequate prep). Success depends on months, or even years, of training, mental preparation and strategy.

The same concept applies to wealth transfer. It’s not about the size of the inheritance at the finish line—it’s about how well-prepared the next generation is to handle it. Whether it’s $1 million, $10 million or $100 million, you can’t expect your children to manage wealth responsibly if they haven’t been informed, educated and equipped to steward it effectively.

So, the real question isn’t how much to pass on to the next generation, it’s how do you prepare them.

The foundation for wealth preservation is built on open, honest conversations. Yet, many families avoid these discussions, believing they’re protecting their beneficiaries (and the family wealth itself) by keeping financial details private. This secrecy often leads to the classic “reading of the will” moment, when surprises and unexpected turns arise, eventually giving way to divisions in the family.

Avoiding these conversations doesn’t just create knowledge gaps—it creates expectation gaps. Children who don’t understand their family’s wealth often make silent assumptions about their future, leading to shock, resentment or family conflict when reality doesn’t match.

The same is true with family businesses. Without proactive discussions, assumptions take root: “I thought I was going to be the next CEO,” says one sibling. “I thought I was getting this portion of the business,” says another. One sibling felt blindsided, another betrayed—each had built their future around an expectation that had never been confirmed. Instead of an opportunity, the business transition became a source of tension.

A lack of communication can also lead to misunderstandings and erode family trust. Take, for example, the husband-and-wife entrepreneurs who sold their business for a significant sum. During one of our meetings, I asked what their young-adult children thought of the sale. To my surprise, they’d hadn’t told them for fear the kids would think they’d never have to work again.

By this point, the information was public—even newsworthy—and easily found through an internet search. I advised the parents to address the sale directly with their children before they found out through outside sources. Otherwise, they risked not getting the full story or encountering inaccuracies— or, worse, creating family conflict.

Ironically, avoiding conversations to prevent children’s sense of entitlement often backfires. If parents don’t talk openly about wealth, children may assume it’s limitless, hindering their ability to understand or appreciate it. Worse, without clarity, wealth becomes a source of silent stress. Some heirs may fear inheriting too much responsibility, while others develop a ‘live for today’ mindset, assuming endless resources without truly understanding them.

Communication alone isn’t enough, though. To prepare the next generation to be stewards of the family wealth, you must instill values that cultivate internal drive, resilience and independence—traits that often motivate entrepreneurs and creators of wealth. This is where business founders and owners have an inherent advantage: they possess a sense of purpose and an inner drive to create and innovate—qualities that are vital for building lasting success.

If the next generation isn’t given the opportunity to develop these traits, they may fail to understand or appreciate the wealth they inherit. This is the so-called “golden cage”—living in a world of privilege without purpose. In such situations, family wealth and legacy can be at risk. Fostering values, independence and responsibility is crucial to ensuring future generations avoid the trap of the golden cage and learn to balance personal fulfilment, financial stewardship and legacy-building.

As you begin to reflect on values, responsibility and transparency, the question of how much is too much or too little naturally fades into the background. It becomes clear that the true issue isn’t the amount being passed down—the number itself is secondary.

So, if the real issue isn’t the amount, but preparation, what does successful preparation actually look like? What are the practical steps to finding the “Goldilocks” balance? That’s what we’ll explore in my next post.