At 34, Sam Dogen retired early in 2012, choosing to live off passive income and investments. His wife followed suit a few years later, retiring at 35. They spent nearly a decade living this way, until 2023, when Dogen purchased an expensive house that changed their financial situation. This decision made him house-rich but cash-poor and prompted him to reenter the workforce after almost 12 years away.
Dogen shared his experience in an interview, reflecting on the choices he made and what he would do differently. He said if he could advise his younger self, he would suggest continuing to work for five more years instead of retiring early. That period coincided with a strong bull market for stocks and real estate, and working longer could have allowed him to save and invest an extra million dollars. With an estimated 4% return, this additional amount might have generated about $40,000 more in passive income annually, which could have boosted his financial security.
He also mentioned that switching to a different office location within his firm, such as London or Hong Kong, could have refreshed his work experience and made his career more enjoyable. This move might have offered new colleagues, clients, and travel opportunities, helping to avoid the feeling of wondering what career paths he missed.
The purchase of his home in San Francisco reduced his passive income from roughly $380,000 to $230,000. This shift caused anxiety tied to financial insecurity and a loss of purpose. To address those feelings, Dogen took a part-time role at a fintech startup but quit after four months. He realized he did not miss aspects of office life like micromanagement or unproductive meetings, and stayed out of the workforce to maintain a lifestyle balance while saving around $10,000 monthly.
Having children after retiring early was another major factor in Dogen’s life. Although retiring early may have lowered his net worth, he said it enriched his life personally. The ability to focus fully on fatherhood during his children’s early years mattered deeply to him. However, he also observed that having kids increased his motivation to seek financial stability, making the combination of early retirement and parenthood challenging.
Dogen advises those considering early retirement to first test living on a reduced income—half of their paycheck—for six months to a year. Experiencing this financial restraint before quitting a job helps reveal whether retiring early is sustainable. He reminds people that active income provides security through paychecks, health benefits, and retirement plans, which investments alone may not replace.
He also suggests preparing for retirement strategically. Instead of quitting abruptly, people should save enough money and negotiate severance packages. This planning offers a cushion that eases the transition and reduces the likelihood of quickly returning to work out of financial necessity.
Dogen says many who take the early retirement leap feel uncertainty and second-guess their decision. Sharing his story on his blog, Financial Samurai, and in his books, he hopes to provide a realistic example of balancing risks and benefits in early retirement.
His experience shows the importance of careful financial planning, testing one’s readiness, and considering personal goals when deciding whether to retire early.
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