Jacob Collums doesn’t speak Arabic. He’s from Texas. But a couple of weeks ago, his employer sent the 31-year old engineer to the Middle East country of Oman. Jacob works for Cameron (recently acquired by Schlumberger). They design and manufacture flow and pressure control technologies for the oil and gas industry.

One of the plants in Oman wasn’t performing as well as expected. Jacob’s two-week assignment was to “fix the problem.” I was intrigued. This fresh-faced engineer looked more like a college kid than the mastermind for a multi-million dollar inefficiency problem.

I met Jacob at Nomadic Desert Camp. It’s a family run company in Oman. They take tourists on desert camel treks and to some of the most gorgeous warm water swimming spots in the world. One night, Jacob and I lay on mats at the desert camp, starring up at the stars. That’s when I began to ask questions.

I want to start by saying that I have few natural talents. I have no ability, for example, to recognize faces. I could meet you at a party. We might talk for hours. But I couldn’t pick you out of a lineup the very next day. Nor can I remember what dresser drawers I put my clothing in. Before my wife put an end to it, I labeled drawers with masking tape: underwear drawer, t-shirt drawer, socks drawer. But I do think that I possess one uncanny skill.

I can usually tell if a young person’s parents paid their entire college bill. This is hardly scientific. But as a personal finance teacher, global nomad and (some might say) an intrusively curious guy, I ask hundreds of young people a similar set of questions.

How did you acquire money when you were a kid? Are you investing money? Do you own a car? If so, do you lease, did you buy a new one, or did you buy one second hand? How much do you pay for rent? Do you carry a credit card balance? What do you do for a living?

Those who paid for some (or all) of their college appear to have better money management skills. They tend to be more frugal. Most earned their own money as kids. Many invest money, buy low cost second hand cars, pay low levels of rent and don’t carry outstanding credit card debt.

Jacob fit the bill. When he was a young child, he helped with his family’s business. That role increased when he was old enough to drive. “As a 16 year old, I woke up at 5am, hooked a homemade trailer to my truck and hit the nicer neighborhood garage sales as soon as they opened. The early bird always gets the good cheap furniture. Then I would take the furniture back to my parent’s store so they could sell it.”

Today, he invests the maximum amount (for a matching contribution) into his company’s 401(k). He rents a room for $400 a month in somebody else’s house. Until recently, he drove a used pickup truck that he bought back in high school. “It finally died a few months ago,” he said. “So I replaced it with a 2011 Toyota Tacoma truck.”

He has also saved money. He has enough cash to pay what remains of his original $65,000 student loan bill or put a down payment on a house.

Before learning about the loan, I felt certain that Jacob’s parents didn’t pay for his college education. I guessed right. He earned it instead. Many students who receive free college rides from their parents still do well. Many end up responsible and highly ambitious.

But the right dose of financial adversity can be a great teacher. As Jacob looked up at the stars he said, “If life were a financial race it would be a 26 mile marathon. I began far behind the start line with student loan debt. But I’ve been training all my life. Most of those who were given a free ride to the 8 mile marker haven’t trained to run. I’ll catch most of them.”

As the English writer and philosopher William Hazlitt once said, “Prosperity is a great teacher; adversity is a greater.”

That doesn’t mean that your child has to pay their entire bill. Each year, college gets more expensive. CNBC’s Susie Poppick reported that the average college graduate leaves school with nearly $30,000 in student loan debt. Many get crushed with two or three times more. But some financial adversity can make people stronger.

Malcolm Gladwell, in his book David and Goliath, says adversity is key. In an interview with Wharton management professor Adam M. Grant, Gladwell said, “We understand linear relationships. We understand diminishing marginal returns. We cannot understand the idea of the inverted U: The same thing that is positive at one level can turn negative at the other – with hugely deleterious consequences.”

In other words, too much adversity can be crushing. Too little can be just as bad. That’s why, when it comes to paying for college, there has to be a sweet spot.

Laura Hamilton, an Associate Professor of Sociology at the University of California, Merced, compared the grades of students at four-year colleges. She found that the more money that parents paid on their children’s education, the lower their academic performance. She feels that it detracted from their drive.

But those who didn’t receive any financial help had lower odds of graduating. Realities of a growing debt may have proved too much. This mirrors Malcolm Gladwell’s inverted U. Too little help can hurt. Too much can hinder. So how much should you pay towards your child’s education?

The sweet spot might be half.