Lessons from a Retired Life Turned Reality Check

Sam Dogen, a former financier turned early retiree, found himself back in the workforce after a decade of living off passive income. At just 34, Dogen thought he had it all figured out, but life threw him a curveball—one that many of us might face when chasing the dream of early retirement.

The Dream Home Dilemma

In 2023, Dogen made a shocking decision: he bought an extravagant home without truly needing it. This leap not only defined him as house-rich but left him cash-poor, a stark contrast to his previous lifestyle of financial freedom. It was a wake-up call that shook the foundation of his financial security, especially as a family man with two kids.

A Need for More Financial Buffer

Looking back, Dogen now wishes he had pushed through just a bit longer in his career. The booming job market between 2012 and 2017 could have allowed him to stash away an additional million dollars—potentially yielding $40,000 more in passive income. He suggests that those contemplating early retirement should seek insights from those who have already taken the leap.

Regrets and Revelations

Dogen realized that instead of leaving his job, he could have explored new opportunities in different cities like London or Hong Kong—environments that could have reignited his passion for work without saying goodbye to his career.

Facing the Fear: Identity Crisis in Retirement

As concerns over providing for his family grew, Dogen made a bold move: he dipped back into the workforce, joining a FinTech startup part-time. This helped him regain both financial stability and that sense of community he'd lost. However, after just four months, he realized he wasn’t cut out for the grind anymore.

Finding Fulfillment Beyond Finances

Despite feeling 'poorer' financially, Dogen acknowledges a richer life in other ways, particularly through being an involved father. Having the freedom to raise his children without the stress of a 60-hour workweek brought him immense joy, but it also ignited a new hunger for status and security to ensure their success.

Advice for the Aspiring Early Retiree

For those dreaming of retiring early, Dogen offers this crucial piece of advice: test your ability to live off of 50% or even 80% of your income for a year. This trial run would clarify whether your retirement dreams are feasible or premature. Additionally, he urges potential retirees to save diligently and seek good severance packages to cushion their transition.

Navigating the Uncertainties of Early Retirement

Dogen warns that the journey into early retirement isn’t always smooth; many experience doubt and regret shortly after quitting, feeling unmoored without the structure of a regular job. His story serves as a cautionary tale, illustrating that while the allure of early retirement is strong, it requires careful planning and psychological readiness.