Nov 18, 2025
According to Yahoo Finance, the average retirement age has increased to 65 for men and 63 for women, up from 63 and 60 respectively in 2001. This moving target is attributed to increased life expectancies, the rising age for full Social Security benefits, healthcare costs, and other hurdles. Meanwhile, funding a retirement likely to last 15 to 20 years often requires a nest egg of $500,000 to more than $1 million, depending on preretirement income.
Investor Challenges Traditional Retirement Approach
One investor, Joseph Drups, believes the focus should shift from accumulating a large sum to generating cash flow. After leaving the Air Force in 2014, Drups sought passive income but initially worked in computer programming and digital marketing. He later turned to investing in existing local businesses, even those barely profitable, in pursuit of recurring income.
“I was buying a job,” Drups said of his initial acquisitions, which produced modest income. His earnings grew from a few hundred dollars a month to five figures of annual revenue, though not enough to retire on. His goal is to scale his strategy with other investors to hire managers and operators.
Financial Samurai Critiques Business Investment Strategy
Sam Dogen, an early advocate of the FIRE (Financial Independence Retire Early) movement, criticized Drups’s approach. “I mean, that’s a terrible passive income idea,” Dogen told Yahoo Finance. “The older I get, the more I want to allocate my cash to 100% passive income investments. You know, stocks, bonds, for example, right?”
Dogen argued that managing a portfolio of businesses creates similar challenges to managing rental properties. He stated businesses like vending machines, laundromats, and car washes are “too much work for too little return.” Dogen combines income from savings, stocks and bonds, rental properties, and publishing royalties for diversified passive income.
FOMO Disrupts Passive Income Success
Dogen recently experienced a setback in his own strategy. “My family and I could have been set for life. Instead, due to my inability to beat back real estate FOMO, I blew up our passive income,” Dogen wrote on his website in June. He sold a large portion of his investments to buy “a nicer home,” resulting in a significant reduction in passive income.
“You know, I went from feeling wealthy to feeling house rich, cash poor. Literally living paycheck to paycheck and hoping like a tree wouldn’t fall on my roof,” Dogen added.
Planning for an Uncertain Retirement Future
Dogen emphasized the difficulty of long-term forecasting. “People are terrible at forecasting their misery,” he said. “In 10 years, are you going to be happy doing what you’re doing now? In 20 years, are you going to be happy doing what you are doing now? If you’re truly miserable, you had better have come up with a plan and save and invested enough to generate enough passive income to give you those options to break free.”
He offered a final piece of advice: “If the amount of money you’re saving and investing each month doesn’t hurt, you’re not saving enough.”
Source: IndexBox Market Intelligence Platform
