“I would rather have a dad who made $100,000 than have than a billion,” Gladwell said in a 2009 lecture at Microsoft that has recently resurfaced on social media. “I think that having a father with a billion dollars would actually be quite crippling to your motivation, and so that’s an advantage that’s actually a disadvantage.”

For Gladwell, who has amassed an estimated $30 million net worth through his work as a journalist, best-selling author, and podcaster, the point isn’t that every child needs to grow up struggling to make ends meet. Rather, there’s a sweet spot between financial hardship and extreme abundance: enough money to provide stability and opportunity, but not so much that a child never has to experience the constraints, disappointments, and work that shape ambition.

The 62-year-old expanded on that idea in his 2013 book, David and Goliath: Underdogs, Misfits, and the Art of Battling Giants. In it, he interviewed one of the “most powerful people in Hollywood,” whom he left unnamed—and the executive made a similar argument.

“My own instinct is that it’s much harder than anybody believes to bring up kids in a wealthy environment,” the person said. “People are ruined by challenged economic lives. But they’re ruined by wealth as well because they lose their ambition and they lose their pride and they lose their sense of self-worth. It’s difficult at both ends of the spectrum. There’s some place in the middle which probably works best of all.”

Paying thousands of dollars for elite education might backfire, according to Gladwell

Education more broadly offers another example of how an advantage can become a disadvantage, with Gladwell questioning whether elite schools always provide the educational advantage their price tags suggest.

“I would love to know on a systematic analysis of why it is the case that you’re better off going to that school than learning how to cope in a far more heterogeneous, rough and tumble public school environment,” he said in the 2009 lecture. 

Beyond price, he always has argued that success isn’t always determined solely by raw ability. Relative standing matters, too—which means surrounding yourself exclusively with high-achieving peers can sometimes work against you.

“If you’re interested in succeeding in an educational institution, you never want to be in the bottom half of your class. It’s too hard,” Gladwell said on the Hasan Minhaj Doesn’t Know podcast last year. “So you should go to Harvard if you think you can be in the top quarter of your class at Harvard. That’s fine. But don’t go there if you’re going to be at the bottom of class. Doing STEM? You’re just gonna drop out.”

There is also evidence that extreme privilege can come with real pressures and pitfalls.

Columbia University researchers found in a 2005 study that children from upper-class families can exhibit elevated likelihoods of substance use, anxiety, and depression in part thanks to excessive pressures to achieve and isolation from parents.

“The American dream spawns widespread beliefs that Ivy League educations and subsequently lucrative careers are critical for children’s long-term happiness,” the researchers wrote. “In the sometimes single-minded pursuit of these goals, let us not lose sight of the possible costs to mental health and well-being of all concerned.”

Growing up without wealth is often also a major motivator

On the opposite end, many business leaders have said coming from humble circumstances became a source of motivation rather than a limitation.

Ulta Beauty CEO Kecia Steelman is one example. She previously told Fortune that she grew up “poor, hungry and determined” in rural Iowa. After getting pregnant as a teenager, she got a job as a floor associate at Target making $8 an hour and began climbing the retail ranks. Last year, she was named CEO of Ulta—the country’s largest beauty retailer with some 1,500 stores.

“Being really grounded and humble with my beginnings, I wouldn’t change that,” Steelman said.

Former PepsiCo CEO Indra Nooyi has similarly credited her upbringing and early struggles with shaping her work ethic. She arrived in the U.S. in the late 1970s to study graduate-level management at Yale University. To pay for her degree, Nooyi worked the midnight-to-5 a.m. shift as a dormitory receptionist before heading to class each morning.

Looking back, Nooyi said the U.S. offered something that mattered more than an easy path to success: the possibility of creating one.

“I remember back in the old days people would say they thought the streets might be paved with gold,” she said. “Maybe they weren’t paved with gold, but they were paved with the possibility of ambition.”

Nvidia CEO Jensen Huang has similarly argued that learning to endure a little struggle—and developing the ability to work through challenges—is part of what separates successful people from the rest.

“Let the suffering come to you a little bit at a time,” Huang said last month at Y Combinator’s Startup School 2026. “Don’t imagine how hard it’s going to be and let all of that turn into anxiety and not doing something about it. You want to imagine in your head, ‘How hard can it be?’”