The Hidden Stress of Early Retirement: When Freedom Brings Unfulfillment
For many workers worldwide, the dream of retiring before age 65 represents the ultimate financial and personal freedom. However, the reality of early retirement often brings unexpected psychological challenges that can overshadow the anticipated bliss of leaving the workforce behind.
The Dream That Turned Sour
Taylor Kovar from Lufkin, Texas, meticulously planned his early exit from the working world. Having worked since his teenage years, he decided at age 23 that he wanted to retire by 35. Through aggressive saving—sometimes setting aside up to 50% of his family's income—and selling his healthcare business, Kovar achieved his goal in late 2021 at age 35.
The next three years were spent traveling to all 50 U.S. states with his family and pursuing hobbies like golf and fishing. Yet, instead of fulfillment, Kovar discovered profound dissatisfaction. "The mental shift that came with retirement was even more difficult," he recalls. The absence of work messages on his phone during a holiday event with his children highlighted his loss of professional identity.
"When you have a job, you have this sense of importance and people depend on you and you depend on others," Kovar explains. "When you go from checking emails several times a day or all day and managing groups all day everyday—and all of a sudden that stops—that's a very hard transition."
The FIRE Movement's Unseen Challenges
Kovar's experience reflects a broader phenomenon among early retirees. Studies indicate that some individuals who leave work prematurely end up suffering from depression and loneliness. This psychological toll deserves greater attention within the Financial Independence, Retire Early (FIRE) movement, which promotes aggressive saving and investing to achieve early retirement.
The personal finance phenomenon gained momentum after the 2008 financial crisis, with pioneers like Sam Dogen of San Francisco—who blogs as "Financial Samurai"—advocating for financial freedom. Yet Dogen's own journey reveals the complexities of walking away from work permanently.
After leaving his six-figure job in 2012 at age 34 with a severance package, Dogen found that transitioning from 60-hour workweeks to leisure activities like golf and tennis left him unfulfilled. Even extensive travel to over 60 countries with his wife couldn't replace the social interactions of workplace holiday parties and client meetings.
"Too much work is not good, and too much leisure is not good," Dogen observes. "Not having purpose makes life kind of pointless."
Rediscovering Purpose After Retirement
Dogen eventually channeled his energy into writing, offering guidance to others navigating the FIRE movement and authoring books on financial freedom. Becoming a father further transformed his perspective on fulfillment.
"I feel like I've been able to hack life by doing both things full-time without guilt: being a full-time dad and a full-time writer," he says. "I now measure fulfillment by something much simpler: being able to provide for my wife and two children while spending as much time with them as possible, given I don't have a traditional job."
The Type A Personality's Retirement Struggle
Peter Sanchez Guarda's experience further illustrates how personality traits complicate retirement. After more than 22 years as an attorney for the U.S. Commodity Futures Trading Commission, a 2024 buyout allowed him to retire at 53 with pension and health benefits intact.
Despite globe-trotting, home projects, and starting a financial law YouTube channel, Sanchez Guarda—a self-described type A personality—found he couldn't simply switch off his driven nature. "You can't go from being type A to sitting on the beach everyday with a beer in your hand," notes the Washington, D.C. resident. "In retirement, I'm still the same type of person."
Even with a substantial investment portfolio eliminating financial need, Sanchez Guarda has resumed interviewing for full-time positions at banks, law firms, and financial technology companies, seeking the structure and engagement work provides.
Redefining Work in the Post-Pandemic Era
The COVID-19 pandemic has fundamentally altered perceptions of work, with increased flexibility making traditional retirement less appealing. Dogen has even suggested that FIRE is becoming "obsolete" as alternative earning methods proliferate.
Kovar's journey came full circle when other early retirees advised him that true freedom doesn't mean stopping work entirely, but rather working on one's own terms. In 2024, he returned to more regular work at his advisory firm, focusing on helping business owners scale their companies without burning out.
"That blend of advisor and consultant work is something I genuinely enjoy, and it's been energizing to be more involved again in a way that feels purposeful and balanced," Kovar reflects.
These stories collectively reveal that early retirement, while financially achievable for some, often requires psychological adjustments and redefined purpose that many underestimate when pursuing their exit from the workforce.
