I was telling a colleague about my younger son’s 21st birthday party when I saw her face change.
My son had asked my wife and me if we’d leave the house for the night so he could have the party at home. We have a great backyard — wooded, a pool, plenty of room to spread out — and it’s always been the place his friends gather. “What an entitled thing to ask,” she said. “For his own party, in your home.”
At first, her response surprised me, but I could see why she would think this was entitled. Her response got me thinking about what entitled means to me.
This is our family home. It has been the hangout since our boys were young. Their friends know my wife and I are welcoming, as long as everyone follows the rules: no drinking and driving (you hand over your keys and you sleep over), and you treat the place with respect. Our sons and their friends have always honored that. So when my son asked us to clear out for the night, he wasn’t asking for a favor from strangers who owned a nice property. He was asking as someone who belongs here, who has some ownership over what this home is and does. That’s exactly how we want him to feel.
A similar thing happened with my older son, though nobody was around to be shocked by it. He was about to do his first triathlon and needed a bike. Mine had been sitting unused for a long time, and he was staying at our house, 45 minutes from his own. If he’d waited to track me down and ask, he’d have had to leave, go home, and come back — and he wouldn’t have had a bike for the race. So he took mine. He didn’t ask first. He knew I wasn’t using it, and he knew I’d be fine with it.
He was right. I was fine with it. Actually, I was proud of it.
In my work with enterprising families, “entitlement” almost always shows up as the villain — the trust-fund kid who expects money with no context for what it took to earn it, no sense that anything is owed back. I do see this kind of entitlement in my work. I see how it can come into being, and I see the damage it can do. But I don’t think all “entitlement” is necessarily a character flaw.
There’s a difference between a child who feels entitled to unlimited stuff with no accountability, and a child who feels entitled to belong — to their family, to the home they grew up in, to the relationships they’ve built trust within. My son didn’t take the bike because he assumes he can take whatever he wants. He took it because he correctly read the relationship: he knew me, knew what I’d say, and knew he could act on that knowledge without waiting for permission he didn’t need. My younger son didn’t ask for the house because he thinks the world owes him a party venue. He asked because he’s spent years earning the kind of trust that made the question reasonable to ask.
That’s the entitlement I want to raise. Not entitlement to have — money, things, outcomes with no work behind them — but entitlement to be: to be known well enough that you can act with confidence in a relationship, to feel enough ownership in something shared that you’re willing to ask for it, or even take it, because you trust that the relationship can support it.
This is the same entitlement I try to help families build into their trusts, their governance structures, their ownership plans, and their parenting. A well-designed trust can do more than distribute money on a schedule — it can be built to reflect and reinforce a beneficiary’s sense of belonging and stewardship, not just their claim to a share. A family business succession plan can hand a rising generation more than equity — it can hand them a seat at the table they’ve been trained, for years, to sit in. The families who get this right aren’t the ones who withhold everything until some arbitrary age. They’re the ones who spend years teaching a child exactly what they can be trusted with, so that by the time real money, real ownership, or real authority shows up, the child isn’t grasping at something unfamiliar. They’re stepping into something they already understand.
My sons didn’t take the bike or ask for the house because they assumed they were owed those things. They acted because years of consistent trust had taught them what they could count on — and taught them how to act on it responsibly. That’s what I want for every rising generation I work with: not entitlement to money, but entitlement to trust, earned and reinforced, long before the money ever arrives.
If you’re a parent building wealth — or an advisor guiding families who are — it’s worth asking: are the structures you’re putting in place teaching the next generation what they can be trusted with, or just telling them what they’ll eventually get?