Roots of Entitlement

Dan Sullivan, founder of the Strategic Coach program, says that “so long as you can write a check to solve a problem, it’s not a problem.” I found comfort in his advice since common, everyday worries tend to bother me.

But it always wasn’t so.

While growing up, money was tight, so writing a check to solve problems wasn’t possible. If I wanted something, like concert tickets, a car, a college (or law school) education, I had to work (or borrow money) to achieve that goal.

Admittedly, as a young man, I was resentful of my friends who had check-writing capable parents. Looking back, however, I appreciate having to face and overcome difficult challenges, as it forged me into the man I am today.

It wasn’t until I reached my forties that I earned the financial resources to solve problems using Sullivan’s method. Just about that time in my life, my own children entered their formative years. Addressing an issue that is germane to others with means, should we write checks to solve our children’s problems? Is that the appropriate strategy for our progeny?

I deal with this very issue in my estate planning practice every day. Clients worry about fostering entitlement attitudes within children and grandchildren, asking me how their trust documents might address these concerns. Loving parents pay for college and post-graduate educations, overseas study, and down payments for first homes. Because of my personal background, I understand those who want to pave a smoother road for their children than the one they traveled.

But is it beneficial to write checks to buffer our children’s difficult and challenging life experiences?

In an interview with New York Times Magazine, clinical psychologist Becky Kennedy emphatically states that’s not a good idea. When asked “How do I not have an entitled kid?” She answered, “…entitlement, what does that mean? It’s the entitlement not to feel frustrated. Because when a kid is like, ‘You didn’t get me a first-class ticket,’ it’s not that they expect ‘first class’ so much as they feel that they shouldn’t have to be frustrated.”

Dr. Kennedy’s point is that to raise a child to healthy adulthood, parents shouldn’t sweep away frustrations, rather they should allow the child to experience them, forcing them to cope. “…When the distress light goes on, we want to operate on a dimmer. If you think about all the worst adult coping mechanisms, they are an attempt to turn a feeling off, not an attempt to dim.”

Everyone has feelings of frustration. It’s part of life. But for the child who has never had to deal, it “…must be [like] having a terrifying experience… to feel something they’ve learned that they should never feel. Using money to always avoid disappointment can lead to that,” she says.

It’s useful for parents to be emotionally validating, instead of financially supportive. Ultimately, when frustrating moments come, the child must be able to say to himself, “Oh, this is part of living; I know how to do this,” rather than, “This should not be happening; I have no skills to deal with it.”

Our children are unique human beings, each different from the other, and different from us. Experts write hundreds of parenting books, but aren’t we all just winging it as circumstances warrant? It’s certainly important to hold ourselves accountable, but that also means to let our children be held accountable – or to even fail from time to time.

As much as writing checks can solve short-term problems, allowing our children to build their own emotional capital pays long-term dividends.
© 2021 Craig R. Hersch learn more at

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