After decades of pinching pennies and watching that retirement account climb, it can be a strange kind of shock to switch gears and actually spend it.
That's where Kevin, a 65-year-old electrician from Georgia, finds himself—14 months away from retirement with a $1.7 million nest egg, no debt outside a mortgage, and enough future income to live on $96,000 a year without even touching the principal. And yet, the idea of watching those savings go down? It's driving him nuts.
"I've been a saver all my life," Kevin told Dave Ramsey on an episode of "The Ramsey Show." "It's just… there's something in my head about seeing those savings going the other direction."
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He's not worried about running out of money. In fact, Kevin said he doesn't think he and his wife will ever need to dip into their investments unless there's a major medical issue. But still—after a lifetime of saving, spending feels wrong.
Ramsey got it. "You spent 66 years building up one muscle—your saving muscle," he said. "What I'm trying to do there is I'm trying to stretch your spending muscle a little bit."
To help loosen that grip, Ramsey gave Kevin a financial assignment: "Put your toe in the water and make yourself, by setting a written goal—you and your wife—that you're going to spend X on fun."
Specifically? "I want you to plan to spend $8,000 on a cruise this year."
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Kevin responded, "Wow… I know that's a lot."
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Ramsey reminded him, "Yeah, I know that's a lot, but you got 1.7 million, dude. I didn't even take the sweat off your interest."
And the spending "fun" didn't stop at tropical getaways. Kevin admitted he's had his eye on a SawStop table saw that runs over $3,000. Ramsey approved. "Perfect. You didn't tell me 300,000—I would've smacked you silly."
The advice was simple: spend with purpose, not recklessly—but spend. Practice enjoying what you've earned.
Ramsey even challenged Kevin to stretch his generosity muscle while he was at it: "Find somebody to give some money to. Generosity goes with spending. They're kissing cousins."
It's a lesson that hits home for plenty of late-career savers. You spend decades saying no, trimming the extras, pushing just a little further—and then one day, you're told it's time to say yes. That shift doesn't come easy. But as Kevin's story shows, learning to enjoy what you've earned isn't reckless. It's part of the payoff.
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