Jennifer was a clerk at an auto parts store in Vista Hills. She got the job because Jackson, her husband, was a mechanic at the Chevrolet dealership and was friends with the owner. But she, like her husband, was a hard worker and added a lot more value than was reflected in her paycheck. It was tough when she got pregnant, but she had earned the owner’s loyalty, and she kept her job. They had a son. And later, three more sons. It was the kind of hard-working lower-middle class family that struggled financially but found ways to pay the bills. They knew they’d never be able to send their kids to college.

Woody, their oldest boy, was a good student and a middle linebacker on his high school football team. He had a lawn-mowing service until he was old enough to get a job in the Chevrolet dealership. He saved his money, bought a junker and fixed it up. Still, he didn’t follow in his father’s footsteps. His real passion was in construction. He was hired by a local builder and after seven years he started his own home improvement business. Over the years it grew, and he expanded into new construction. By the time he was forty his operation had become a 100-million dollar commercial construction company with contracts all over the state.

Fran, who lived in a spacious home on a horse ranch just outside Vista Hills, didn’t know Jennifer. She spent her days gardening, playing tennis and shopping with her friends. Her husband, Ted, was a partner in his father’s law firm. They had a son and a daughter. Ted’s plan was to send his son to Harvard Law School so the boy could join the law firm. Their lovely daughter would marry into wealth.

Sinclair, their son, drove a Corvette to a private school and was very popular. He didn’t take his studies seriously, so he wasn’t accepted into any of the Ivy League universities. But he attended the University of Miami, where he spent a lot of time partying with his buddies. And girls, of course. He didn’t share his father’s interest in law, and that career never happened. After graduation, he wasn’t sure what he wanted to do. So he returned home where he spent most of his days playing golf at the country club. He was a scratch golfer, but by the time he was forty he was still living at the ranch, having settled into a comfortable lifestyle.

Both Woody and Sinclair ended up with similar economic advantages. In fact, they became acquaintances and sometimes played in the same foursome at the Vista Hills Country Club. But of course, they were two quite different people. Woody was a busy entrepreneur who worked hard doing what he loved. And Sinclair was, well, an aimless playboy who depended on his daddy’s money.

Which reminds me of another story.

About twenty years ago, a retired CEO friend of mine called to ask for a favor. Would I talk to the son of his best friend to help the young man decide what kind of work he’s best suited for? The “young man” was in his early forties, and he hadn’t worked a day in his life. Instead, he had used the proceeds of a trust fund annuity to support a comfortable lifestyle. He got into trouble when interest rates fell and he dipped into the principal to make up the difference. When his parents refused to bail him out, he was faced with getting a job. He had no idea what to do next.

I decided to talk with him on the phone before committing to a coaching session. After putting him at ease I asked him, “Assuming you could make good money doing anything you want and enjoy the work at the same time, what would you like to do?” After a long pause, he said, “How about racing cars?”

I told him about a career assessment that would reveal the kinds of work he’d find most enjoyable. “I’m not really interested. Can we work this out without the test?” He and I never made it to the coaching session. I didn’t think I could help him. He expressed no interest in any career, and he would do anything to avoid getting a job.

On another occasion, I spent a couple days coaching Ben, my retired friend’s oldest son. He had pursued several opportunities set up through his father’s influence, but he had failed at each of them. At this point, he didn’t know what to try next. My goal was to find out what his passion was or, failing that, what he was interested in.

After two days, I discovered something strange and unexpected. He had no passion or interest in anything except his three children. It was as if the fire in his belly had gone out. Or maybe there had never been any fire there in the first place. The only thing he showed an interest in was the future date when the first phase of his trust fund would kick in. I couldn’t tell my friend this. Instead, I recommended that Ben study to become a certified financial planner. I knew Ben wouldn’t want to do it, but he had a family to provide for and this seemed to suit his experience and personality.

And then there was this boyfriend of a friend of mine, who was living off of a $150 million inheritance. He was one of the oddest people I’ve ever met. No matter what topic came up in conversation, he dismissed it as silly and uninteresting. It wasn’t arrogance. Like Ben, the fire in his belly had gone out. He honestly didn’t understand why people cared about things. Which is OK, I guess, financially speaking, if you have $150 million in the bank.

I could tell other stories, but I learned that all these people had two things in common. One, they had never had to strive for anything in their lives. Everything had been given to them.

And two, they had no desire to work at anything. They had never worked before, they weren’t familiar with work, and they didn’t want any part of it.

Tragic.

Why did this happen? The answer comes from Aristotle, who said this over 2,000 years ago:

“Whatever we learn to do, we learn by actually doing it: men come to be builders, for instance, by building, and harp players by playing the harp. In the same way, by doing just acts, we come to be just; by doing self-controlled acts, we come to be self-controlled; and by doing brave acts, we become brave.”

These people had grown up without having to work for anything. Consequently, work was strange and unthinkable to these success-disabled people.

And this from Duke basketball coach Mike Krzyzewski:

“The only way you’re going to grow is to be in difficult situations.”

These inheritors of wealth had never known difficulty, so they had grown into adults who had no idea how to deal with it.

I hasten to say that not all children of wealthy families turn out this way. If made to work and earn their way while growing up, they can learn to be achievers. The problem comes when the parents feel that because of their financial advantages, it’s their role to protect their children from challenges and make sure they have whatever they want.

Also, parents don’t have to be wealthy to make this mistake. A friend of mine sent her daughter to private school and had to deal with an interesting issue. Most of her daughter’s friends came to school in brand new cars. And of course she wanted one, too. My friend informed her daughter that she was 16 and could have any car she wanted – if she was willing to pay for it. Today this young woman is a fast-tracker in an investment brokerage firm, full of self-confidence and positive self-esteem.

“I didn’t want my kids to have to struggle the way I did when I was young.”

I don’t know how many times I’ve heard this. They feel that being a good parent means giving their kids everything they didn’t have. They don’t appreciate the cause-and-effect connection between their own early struggles and their subsequent successes in life. In my opinion, protecting kids from the challenges of life is the second greatest mistake a parent can make. The greatest mistake, of course, is the failure to express unconditional love.

I must also add that not all disadvantaged kids use adversity to become strong for life. There are plenty of success stories, but there are as many stories about people who blamed others, accepted their condition or were beaten down by it. Adversity can be a magical door of opportunity, but it takes strength to walk through it.

It all comes down to this: parents need to heed the words of Aristotle and Coach K. Whether they are disadvantaged, live a comfortable middle-class lifestyle, or are “set for life” financially, it’s important to give kids a chance to strive and earn what they want. Youth passes quickly, and this window in time is when young people prepare themselves for adult life.

Parents who consciously arrange opportunities for their kids to strive and learn the behavior patterns of personal strength – and then support them with coaching and encouragement – are giving them one of the greatest gifts of all.

More about this in my new book: How Your Teen Can Grow a Smarter Brain.

You can grow the bond with your child through better listening. Download the FREE ebook, Listening to Understand.