A 33-year-old woman with no debt, a stable income, and even a paid-off master's degree called into "The Ramsey Show"—not for advice on what to fix, but to ask a more haunting question: Why does it feel like I'm still losing at life?
Despite earning $60,000 a year, owning a home with just $140,000 left on the mortgage, and having no other debt, the caller—Hillary—admitted, "I just see a lot of people my age or younger bragging and boasting about their nice cars, houses, and vacations, and I just feel like I'm losing at life."
Rather than rush to soothe her, Dave Ramsey got right to the root of what he believes is fueling that discontent.
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"This is the problem," Ramsey said. "The millennial, your generation, was one of the first ones to really, really struggle with it."
He was referring to the social media comparison trap—a constant bombardment of filtered, curated glimpses into the seemingly perfect lives of others.
Ramsey explained that in the past, people compared themselves to the Joneses—neighbors with real, visible lives. You saw the new car in the driveway, sure, "but you also saw them have big fights, and you also knew that their kids were messed up."
"But on social media," he warned, "you're only thing you're looking at is the highlight reel… Nobody posts on there, ‘My husband just got me a 1992 Honda. #Blessed.'"
Even the exotic vacations people post about don't necessarily tell the full story. Hillary mentioned hearing coworkers mention trips to the Bahamas and brand-new Escalades, which left her questioning her own choices.
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But Ramsey was quick to set the record straight.
"That Escalade is actually really an amazing car… and 99% chance that's not real money that bought that."
In fact, had Hillary simply called in and said, "I'm a 33-year-old single female, I make 60 grand, I only have $120,000 left on a house I bought myself," Ramsey said the reaction would've been pure celebration.
"We would be going, touchdown! We would celebrate you as like the model," he told her. "I hope my daughter Josephine is in that kind of situation… You're amazing. You've done a great job. You're doing it right."
Co-host John Delony chimed in, likening Hillary's comparison dilemma to indie filmmaking: "You're the indie filmmaker and all you have is a camera and you're telling real stories, and you can't compete with the Godzilla movies that are made in computer labs."
Hillary admitted she had also just paid cash for her master's degree—something she confessed had her second-guessing the trade-off. "All that money I had saved, I'm just like, that could have been a vacation or a car. I shouldn't have done that."
But Ramsey wasn't having it.
"Dude, you just put an investment in yourself for the next 50 years of your life. You traded a master's degree for Bahamas. This is a good trade."
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He shared a personal story to drive the point home. At 28, Ramsey was driving a Jaguar—and went broke. What followed was a season of driving a "hooptie," including a beat-up loaner car that was 90% Bondo with a torn vinyl roof that "filled up with air like a parachute" when he drove.
"I used to have to pull up in those hoopties… Meanwhile I'm sitting next to people in nice cars that just got home from the Bahamas, and I'm looking at them going, what am I doing wrong?"
But perspective changed everything.
"Today, if you did that… the average car payment at that stoplight is $750."
As the call wrapped up, Delony offered Hillary a final insight: beneath all the comparison, maybe the real issue was something deeper.
"How much of these videos you're seeing… are reinforcing a sense of loneliness?"
"Probably a lot," Hillary admitted. "Because I feel like they just can go do whatever, you know?"
Delony's advice was simple: "Start creating opportunities to have friends and community and connection and laughter right where you live… and it's going to make the other shiny stuff… not be that big a deal."
Because no matter what TikTok or Instagram tells you, success isn't about Escalades or beach resorts. Sometimes, it's just about being 33, debt-free, and already winning—even if you don't feel like it.
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