By the time you hit 61, you'd hope to have some financial footing, maybe even a retirement fund you could glance at without breaking into a cold sweat. That wasn’t the case for Teresa, a caller on Dave Ramsey's show in September 2023. She had $69,000 in debt, a $26,000 tractor and a lot of regret. 

"I'm knocking on the door of 61," she said, her voice carrying a mix of nerves and determination. "I have no retirement money saved up whatsoever," Teresa explained. She's been working on Ramsey's famous Baby Steps, but all she has right now is $1,000 as her emergency fund. With Social Security still a few years off, she asked the million-dollar question: Should she start contributing to her 401(k) with a company match, even though she's still on Baby Step 2?

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Ramsey didn't sugarcoat it. "So you're 61 and have no money?" he clarified, setting the stage for the kind of tough-love advice he's known for.

Teresa's situation unraveled further. She makes $67,000 a year but owes $11,000 on a student loan that's been around since 1999, $18,000 on a car, $12,000 on a personal loan and $26,000 on a Kubota tractor.

When Ramsey asked why she had a tractor worth more than her net worth, Teresa admitted, "Well, we're country. I use it to clear deer leases and our hunting area." Ramsey didn't hold back. "Broke people don't have $26,000 tractors," he said. She tried to defend it, explaining she'd attempted to sell it, but no one wanted to pay what she owed. Ramsey shot back with a solution: "Go to the credit union, borrow the $5,000 difference and get this tractor sold."

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But the tractor wasn't the only thing Ramsey took issue with. Teresa owns seven acres of land worth about $4,000 in total. That tidbit left him stunned. "You've got a $26,000 tractor for a $4,000 piece of land? You guys are in emergency mode, girl."

Teresa tried to laugh it off, calling her tractor purchase "spur-of-the-moment." Ramsey didn't have it. "It gives you joy, but not as much joy as being broke is stealing from you," he said, laying it out bluntly.

The conversation turned to action steps. Ramsey advised Teresa to sell the tractor and car and get down to the bare necessities. "You need a $2,000 car. You're trading that $18,000 car for $100,000 in retirement. You're trading that tractor for another $150,000."

The advice didn't stop there. "Every deer in the area should be scared," Ramsey joked, pushing Teresa to hunt down every dollar she could find. "Your husband needs to be afraid he's going to get sold next."

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It wasn't all jokes, though. Ramsey acknowledged the challenge ahead. "You've lived this way for decades. Turning it around is going to feel uncomfortable. People in your life are going to think you've lost your mind. But you're fighting for a reasonable last couple of decades."

Before ending the call, Ramsey gave Teresa some advice laced with humor. "Every time you do something smart, I want you to say, ‘I'm doing this because I'm a country girl.' Don't do anything dumb and blame it on being a country girl. Quit blaming dumb stuff on country girl. Blame smart stuff on country girl because country girls do smart stuff."

CBS News reports that more than one in four older Americans are heading into retirement with no savings at all and with the youngest baby boomers hitting 65, the problem isn't getting any smaller. Living out the "American dream" in retirement feels out of reach for millions. 

For those in their 60s still scrambling to figure it out, consulting a financial advisor could be the difference between making ends meet and facing years of stress. It's not too late to make smarter choices – even if it means parting ways with a $26,000 tractor.

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