He Left His Old Job To Become An Entrepreneur And Doubled His Income. His Family Thinks He Should Go Back. Dave Ramsey Says That Would Be Insane
He Left His Old Job To Become An Entrepreneur And Doubled His Income. His Family Thinks He Should Go Back. Dave Ramsey Says That Would Be Insane
Adrian VolenikMon, February 23, 2026 at 11:31 PM UTC
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At 25, he's debt-free, fully funded his emergency savings, built a separate business emergency fund and doubled his income. But instead of celebrating, he feels guilty.
After seven years in construction, the California handyman left his employer to work for himself. He went from making about $60,000 a year to roughly $120,000. His former company wants him back and his family says he charges too much. Now he's wondering if he made a mistake.
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The young entrepreneur, Brian, brought his dilemma to “The Ramsey Show,” where hosts Dave Ramsey and co-host Ken Coleman didn't hesitate.
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Ramsey got straight to the math. “I'm confused where the mistake might be,” he said after hearing the income jump. “Am I missing something?”
When the caller mentioned the possibility of returning, Ramsey told him to tell them, “I don't have brain damage, all right?”
Still, Brian admitted he felt loyal to his old company, but again Ramsey pushed back. “There's never been anyone that worked at Ramsey that left here and made double that I suggested they should come back for half,” he said. “Never. If they can make double somewhere else, I would like that for them.”
The caller explained that his relatives think charging professional handyman rates is excessive. Ramsey framed the real issue: misplaced guilt.
“So the only reason you would go back to work for the other company is because your relatives say you charge too much and it's evil that you've become wealthy doing this at 25 years old?” Ramsey asked.
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Coleman said many families misunderstand entrepreneurship. Some assume working for a large company or the government equals safety. But recent history tells a different story. Big brands have laid off thousands of workers overnight. Size doesn’t automatically equal security.
Ramsey shared a personal story about a relative who kept asking when he would “get a real job.” That year, he said, he earned more than her husband, who worked a corporate job had made in his entire lifetime. “She was worried about me because she was worried it was unstable,” he explained. “She misjudged where security comes from.”
According to Ramsey, real security comes from your ability to produce income.
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You Always Work For Yourself
“When you work for a company, you just have one client,” he said. “When you work for yourself and you have a bunch of customers, it's no different.”
He reminded Brian that skilled trades are in high demand. “If you just show up, you can charge about anything you want to charge,” Ramsey said, adding that he recently spoke with a handyman who made $300,000 in a year.
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For this 25-year-old, the numbers are strong. He's debt-free, cash-flowing his life and running a profitable business with satisfied clients. Going back for half the income out of guilt would result in shrinking his opportunity.
If anything, Ramsey's message was that growth sometimes makes other people uncomfortable. That doesn't mean you're wrong.
For high earners building businesses or managing six-figure household incomes, it may also help to get an outside perspective. WiserAdvisor's free tool matches you with a vetted financial advisor who fits your needs, with no obligation to hire. It's designed for households earning $100,000 or more who want to book a free consultation and make confident money decisions.
In the end, Ramsey told the caller he was proud of him. He has proven he can create income on his own. “That young man right there, wouldn’t you love to have him in your house fixing stuff?” he said.
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Source: “AOL Money”
