The Generosity Trap: Parenting, Entitlement, and the Struggle Over Money
Money is never just about money. It’s about childhood. It’s about what we grew up with, what we lacked, what we feared, what we resented. It’s about relationships—who had control, who felt deprived, who felt reckless, who felt responsible. And, most of all, it’s about the stories we carry without realizing we’re still acting them out.
For Ben and Mia, money had always been a quiet but persistent source of tension in their marriage. Not because they didn’t have enough of it, but because they experienced it so differently.
Ben came from a family where money meant security, and security meant control. You spent on what was practical—on things you could see, touch, and justify. A house was an “investment.” A car, as long as it was reliable, made sense. Tools, appliances, sturdy furniture—those were worth it. But anything that felt unnecessary, indulgent, or just about comfort? That was frivolous. He had learned from his father that money wasn’t for ease or pleasure; it was for function and stability.
And more than that, he had learned that if you wanted something, you had to take it for yourself before someone else did. His father had always reached for the biggest portion at dinner, had always made sure his own needs were met first. That instinct ran deep in Ben. Even though he loved his kids, there were moments when Mia could feel it—like he had to make sure he was taken care of before he could even think about generosity. Like generosity was something extra, something optional, only available once all other concerns were locked down.
Mia, on the other hand, had grown up in a home where money carried a different kind of charge. Her father had been careful, controlled, always weighing decisions, making sure there was enough. Her mother, by contrast, spent freely, without hesitation. If something made life easier, she would say yes without overanalyzing. And this constant push and pull—tightness versus ease, control versus flow—had shaped Mia more than she realized.
She wanted to be generous, to say yes easily, to give without overthinking. But she also carried that other voice inside her, the one that worried about paying too much, about being wasteful, about not being smart with money. She didn’t like the feeling of getting ripped off. She liked to think of herself as free with money, but the truth was, she warred with herself—between the part that wanted to spend without stress and the part that needed to make sure she wasn’t being foolish.
And now, as parents, this conflict between them—and within them—was playing out through their kids.
Their oldest, a teenager, had started calling Ben out for being cheap. And at times, Mia agreed. Ben could hesitate too long, analyze too much, treat even small expenses like they needed justification. But she also saw where it came from. He wasn’t just being tight-fisted for the sake of it. He was worried—worried about raising entitled kids, worried about them not appreciating what they had. He saw entitlement everywhere, and he didn’t want their children to fall into that trap. If that meant saying no more often, so be it.
There was another layer too. Ben was deeply committed to sustainability. He hated waste, loved to recycle, and took pride in finding secondhand treasures. If something could be repaired, reused, repurposed, then why would they ever buy new? But this, too, sometimes became a roadblock. A simple purchase could stretch into an exhausting hunt for the “right” used version. Sometimes, they ended up with something that didn’t quite fit, but Ben had gotten a deal, so it had to be good enough.
Mia, meanwhile, just wanted things to work. She didn’t want to spend weeks searching for a secondhand desk when they could just buy the right one today. She didn’t want to overthink whether their child really needed a new jacket or if the old, ill-fitting one would do for another year. She wasn’t careless with money, but she also didn’t want to feel like every decision had to be a battle.
And then there was the bigger question: How do they raise kids who are responsible with money but not anxious about it? Who are generous but not reckless? Who understand the value of a dollar without feeling like life is always about calculating, weighing, hesitating?
Ben and Mia were trying to find that balance. Trying to untangle their own pasts so they didn’t just unconsciously pass them down. Trying to teach their kids about money in a way that wasn’t about deprivation or excess. And trying to meet somewhere in the middle—where responsibility and generosity could coexist, where environmental values didn’t turn into rigidity, where their kids could learn the lessons they needed without feeling like every request was a test.
Because at the end of the day, neither of them wanted their kids to be wasteful. Neither of them wanted entitlement. But they also didn’t want their kids to carry stress, to feel that money was always something to debate or justify.
They wanted their children to learn how to spend wisely and how to enjoy. How to be thoughtful and how to say yes without guilt.
How to know when to be responsible, and when it’s okay to be frivolous.
Because sometimes, flow and ease aren’t careless. Sometimes, they’re the antidote to scarcity.
And maybe, as parents, they were still learning how to do that for themselves too.
Are you looking for help with your relationship? Do you feel that a relationship coach could help you working on your couples skills? Is communication an issue? Have you ever considered couples therapy or counseling? As a psychotherapist and relationship coach, I am uniquely positioned to help you through these moments of disconnect and conflict.
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