Here's a wild scenario that probably keeps financial advisors up at night: A 37-year-old project engineer who spent six years at Tesla Inc. (TSLA) is sitting on $650,000 worth of company stock. She earns $70,000 annually, pays $1,000 a month in rent, and carries $20,000 in debt she plans to eliminate this year. Her cash savings? Zero. But she's holding tight to those shares, waiting for them to hit the magical $1 million mark. She's nervous about the tax bill and convinced the stock has more room to run.

Not Investing, Just Rolling The Dice

Personal finance experts Dave Ramsey and George Kamel tackled this situation on an episode of "The Ramsey Show," and they didn't hold back. "This does border on gambling," Kamel said. "Waiting for your single stock to go up another 30-something percent so that you can cash out at the right time—that scares me. Who knows what's going to happen with Tesla?"

Ramsey put it even more bluntly. "I'm not dissing Tesla, but I'm not buying it," he said, hammering home the importance of diversification. "If you're 37 years old and you have $650,000 in cash stacked in the middle of the kitchen table, what do you do with it? Go buy Tesla stock? No. Go buy any single stock? No. Go buy a house? Yes."

Sure, she'd face a tax bill of roughly $100,000 in long-term capital gains. But Ramsey wasn't sympathetic. "Welcome to making money. Sorry, but that goes with the territory."

His advice? Cash out immediately, wipe out the debt, and buy a home with no mortgage. With housing costs eliminated, she could save thousands every month and invest aggressively in diversified accounts. "Now you can load your 401(k)s, your Roth IRAs. You can stack cash. You're going to have zero debt and no house payment of any kind," he explained. "You're going to have another million dollars in just a few minutes if you do this."

The Case Against Single Stock Concentration

This isn't just situational advice. Ramsey has long maintained a firm stance against single-stock investing. "I don't buy single stocks. And the lack of diversification is one of the reasons," he once said.

The risk isn't just market volatility. It's that you're completely at the mercy of one company's decisions and reputation. "They can make the decision to do anything stupid and suddenly you could have a Bud Light moment," Ramsey warned. His co-host chimed in: "Or a Tesla moment, or even a Cracker Barrel moment."

Ramsey's preferred approach? Mutual funds that spread risk across dozens or hundreds of companies. "If you had $1.8 million in 90 to 200 stocks, you'd be perfectly safe compared to having 34% of your net worth in one singular company's behaviors," he said. "You can see the stock just nosedive. I don't want that. I don't have control over that. So, I'm not putting my money in that."

The engineer's situation highlights a common problem for employees who accumulate significant company stock: knowing when to let go. The emotional attachment to shares that have performed well can cloud judgment, turning what should be a straightforward financial decision into a high-stakes guessing game about future performance.