The Real Root of Entitlement Isn’t Wealth. It’s Secrecy.
This article is Part 1 of our Family Wealth Stewardship Series. View the full guide.
What we Get Wrong About Entitlement
Many business owners and high-net-worth individuals approach wealth planning with one major fear: “I don’t want my kids to feel entitled.”
It’s an understandable concern. You’ve worked hard to build something lasting. You want to protect it, not just from taxes or bad investments, but from misaligned values in the next generation.
But here’s the truth: communicating your intentions or preparing your children doesn’t cause entitlement. Entitlement is a mindset that forms over time. It’s not the result of one act; it’s the result of inaction.
Entitlement doesn’t stem from access or lifestyle. It stems from exclusion, secrecy, and a lack of learning opportunities. Avoiding the conversation may feel like caution, but often, it does more harm than good. It leaves children uninformed, emotionally disconnected, unprepared to handle what’s coming, and lacking an appreciation for what they’re receiving.
This isn’t about spoiling the next generation or surrendering control. It’s about something much more disciplined: treating the preparation for wealth transition with the same intention, structure, and long-term thinking that went into building your business.
The Sacrifices They Already Made
If your children grew up while you were building your business, they were part of the journey, even if they never set foot in the office.
They sacrificed alongside you. They missed time with you. You missed their events. They adapted to the stress you brought home and grew up in the shadow of something demanding and important. Your success didn’t happen in isolation; it happened around them. And often, at a cost to them.
So when the business is sold and a liquidity event occurs, the proceeds don’t arrive in a vacuum. They come with history and in many cases, expectations. Acknowledging your children’s role and sharing the rewards of liquidity doesn’t spoil them. It honours the sacrifices they’ve already made, even if they didn’t choose to make them.
“It was all for you”… Until it wasn’t
Parents often say they want to “give my kids more than I had.” But imagine the message that is sent when, after years of being told, “I’m building this for you,” a child is suddenly excluded from the process out of fear that they’ll feel entitled. What changed? Not the child, only the means to follow through.
Confusion and sometimes resentment can take root in the gap between intention and action.
And here’s the reality: entitlement isn’t caused by wealth. It’s caused by a lack of context and preparation.
What Research Tells Us
A landmark study featured in Preparing Heirs found that 70% of intergenerational wealth transfers fail, not because of taxes, investment performance, or legal structures, but because of a breakdown in communication and trust within the family.
Preparation doesn’t begin when a child inherits money. It starts when they’re old enough to grasp what you value and why. Expecting them to adopt a stewardship mindset overnight is unrealistic and unfair.
If you want the next generation to carry your legacy forward, the solution isn’t to shut them out. It’s to bring them in early, honestly, and with structure.
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