A striking contrast emerged on the streets of Chicago when personal finance expert George Kamel asked strangers about their debt: while some young Americans are trapped under mountains of student loans they expect to “die with,” others have cracked the code to building wealth before their 21st birthday.
The interviews revealed a financial reality that’s reshaping American life—a third of Americans are struggling or in crisis with their money, and over half are living paycheck to paycheck, according to Kamel’s findings. But the stories also exposed a critical divide: those who’ve escaped debt’s grip versus those who’ve resigned themselves to it.
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The Student Loan Trap Has Six-Figure Jaws
The debt landscape spans a staggering range. Some interviewees carried $20,000 to $25,000 in student loans—manageable but burdensome. Others revealed the true scale of America’s education debt crisis: six-figure balances, potentially reaching $500,000 for advanced degrees like dental school.
One young person with $25,000 in student loans expressed a fatalistic attitude that caught Kamel’s attention. They said they had “no plans on paying it off” and expected to “die with it.". Kamel challenged this cynicism head-on, warning that student loans cannot be discharged through bankruptcy and can lead to garnished wages. He compared creditors to “the mafia,” urging the individual to “drop the cynicism and start betting on yourself.”
Even those aggressively tackling their debt face marathon repayment timelines. Six-figure debt holders reported repayment plans spanning 15 years, even when “going hard on it.”
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Medical Bills and Emergency Debt Add Fuel to the Fire
Student loans aren’t the only culprit. Several Chicago residents reported actively paying off medical bills ranging from $4,500 to $5,000. Others had taken out personal loans to cover emergencies—a consequence of having insufficient savings when life throws a curveball.
One interviewee took on what they called “intentional debt” by financing a vehicle despite making a 50% down payment and having the cash to avoid the loan entirely. The reason? Building credit. It’s a strategy that reflects how deeply the credit system shapes American financial decisions.
The Blueprint for Staying Debt-Free Exists—But Requires Sacrifice
The most compelling stories came from those who avoided debt altogether. A 20-year-old certified nursing assistant making about $8,000 monthly successfully stayed debt-free, paid $20,000 in full for a used car, and bought a house at age 20 in Florida. The secret? Hard work, talent, and living below her means while saving aggressively.
Other debt-free individuals shared their strategies. One person cited growing up “pretty poor” as motivation—”enough to traumatize” them into avoiding debt their whole life. Others recommended union jobs and trade apprenticeships, working “one and a half jobs” until becoming debt-free.
Full-ride scholarships through financial aid or college athletics—which Kamel said requires “significant dedication and sacrifice of time and energy”—provided another path.
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Two Philosophies: Aggressive Repayment vs. Strategic Balance
Among those carrying debt, strategies diverged sharply. One person plans to eliminate $14,000 in car and personal loan debt before year’s end by cutting extra expenses. Another with $20,000 in student loans and $16,000 in savings chooses to budget for gradual repayment while building savings simultaneously.
Kamel shared his own success story: paying off $38,000 in 18 months through side hustles and frugal living after college.
A software developer’s approach illustrated a middle path—choosing not to pay off $20,000 in student loans immediately despite having substantial savings, opting instead to balance debt repayment with building a financial cushion.
The Bottom Line: Debt Never Improves Your Financial Situation
Kamel’s conclusion carried a stark warning: debt “never makes your financial situation better” and represents “robbing of your future income and your financial future.” For those making only minimum payments, high interest rates can cause balances to balloon. Combined with unexpected health issues or emergencies, debt can make or break a person’s financial future.
The Chicago interviews painted a picture of an America divided not just by income, but by financial philosophy—where some are building generational wealth in their twenties while others have already surrendered to decades of debt servitude.
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