Jade Small
Jade Small
October 24, 2024 ·  8 min read

45-year-old ‘fake retiree’ shares the most surprising lessons he learned when he tried to retire early

In June 2012, at the age of 34, I made a bold decision after dedicating 13 years to the fast-paced world of investment banking: I chose to step away. With a desire for freedom, I negotiated a severance package, opting for an early retirement that would allow me to sustain myself through passive income generated from my rental properties, stock dividends, and e-book sales.

Harsh Realities

However, within a year, the idyllic vision of endless travel and leisure quickly turned into a reality I hadn’t anticipated. Boredom crept in, and I grappled with feelings of identity loss. It became clear that I craved an outlet—a pursuit that would reinvigorate my sense of purpose and engagement. Although it’s been over a decade since I left full-time work, I don’t view myself as truly retired; I prefer to label myself a “fake retiree” because I’ve embraced various side hustles that keep my days vibrant and fulfilling.

Here are six enlightening lessons I’ve gleaned from my decade as a “fake retiree.”

Embracing Your Unique Path

The term “fake retirement” often draws skepticism. Many readers have pointed out that if I’m still earning an income, I can’t truly be retired. And they have a point! However, I believe it’s important to celebrate the unique paths we carve out for ourselves. Many early retirees find joy in activities like blogging, creating online courses, or selling artwork. Personally, I manage my blog, Financial Samurai, and spent two years pouring my heart into my personal finance book, “Buy This, Not That.” Far from lounging on a beach, many of us are working passionately on projects that inspire us.

Financial Needs are Ever-Changing

When I first retired, an annual passive income of $80,000 felt like a dream come true. Fast forward to 2015, when my wife joined me in early retirement; our financial landscape shifted dramatically, requiring us to aim for $160,000 to account for her income loss. With the arrival of our son in 2017 and daughter in 2019, our financial demands only increased. Today, paying $2,200 monthly for healthcare and $5,000 for preschool feels overwhelming. The rising cost of living, driven by inflation, means we continually reassess our budget, leading us to acquire more rental properties and invest in resilient assets like healthcare stocks.

The Lure of Traditional Work

Since leaving my corporate job, I’ve often felt the magnetic pull back to traditional employment. The first time I encountered this longing was just six months post-retirement, as I missed the camaraderie of working toward a common goal. The second wave of doubt hit after our son was born; I feared financial instability and the challenges of new parenthood made me think a job could provide a much-needed escape. The final time was during the pandemic, as I observed friends thriving in a balanced remote work environment. Ultimately, I realized that even a flexible job wouldn’t grant me the freedom I craved; I would still be accountable to others.

The Power of Authentic Expression

One of the most liberating aspects of financial independence is the ability to express my thoughts freely. In traditional workplaces, I often felt compelled to hold back, wary of how my words might affect my professional standing. Now, I can share my authentic self without hesitation. For instance, when a producer approached me about narrating my audiobook, I insisted on having a narrator who reflected my identity as an Asian-American. Speaking up ensured that a deserving Chinese-American voice was chosen—a choice I may not have had the confidence to make in a corporate setting.

Legacy Becomes a Guiding Light

With the luxury of time, I’ve found myself reflecting deeply on the legacy I wish to leave behind. Early retirement allows for introspection about what truly matters. For some, that may manifest in scholarships or charitable endeavors, while for me, it’s about empowering others with financial wisdom. Throughout the pandemic, the thought of my children sharing my book during show-and-tell kept me motivated. I’ve learned that nurturing causes that resonate with you, mentoring others, and sharing your blessings contributes to a meaningful legacy.

Shifting from Certainty to Probability

As I navigate this unconventional path, I’ve come to embrace a mindset focused on probabilities rather than absolutes. It’s essential to create as many opportunities as possible for your future self. By saving and investing wisely, you open doors for various life choices, whether that means transitioning to a more meaningful job or enjoying a few years off for family care. My decision-making philosophy centers on a 70/30 approach: if I perceive a 70% likelihood that I’m making the right call, I’m willing to take that leap. I recognize that a 30% chance of error exists, but I view mistakes as valuable learning experiences that pave the way for better choices ahead.

Conclusion: Finding Fulfillment Beyond Traditional Retirement

Reflecting on my decade of “fake retirement,” I’ve learned that fulfillment is not a one-size-fits-all concept. Whether you choose to step away from traditional work or carve out a new path, it’s crucial to prioritize what resonates with you. Embrace the journey, make choices that align with your values, and remember that the beauty of life lies in its unpredictability. After all, it’s not just about retiring; it’s about living fully on your own terms.

In June 2012, at the age of 34, I made a bold decision after dedicating 13 years to the fast-paced world of investment banking: I chose to step away. With a desire for freedom, I negotiated a severance package, opting for an early retirement that would allow me to sustain myself through passive income generated from my rental properties, stock dividends, and e-book sales.

However, within a year, the idyllic vision of endless travel and leisure quickly turned into a reality I hadn’t anticipated. Boredom crept in, and I grappled with feelings of identity loss. It became clear that I craved an outlet—a pursuit that would reinvigorate my sense of purpose and engagement. Although it’s been over a decade since I left full-time work, I don’t view myself as truly retired; I prefer to label myself a “fake retiree” because I’ve embraced various side hustles that keep my days vibrant and fulfilling.

Here are six enlightening lessons I’ve gleaned from my decade as a “fake retiree.”

Embracing Your Unique Path

The term “fake retirement” often draws skepticism. Many readers have pointed out that if I’m still earning an income, I can’t truly be retired. And they have a point! However, I believe it’s important to celebrate the unique paths we carve out for ourselves. Many early retirees find joy in activities like blogging, creating online courses, or selling artwork. Personally, I manage my blog, Financial Samurai, and spent two years pouring my heart into my personal finance book, “Buy This, Not That.” Far from lounging on a beach, many of us are working passionately on projects that inspire us.

Financial Needs are Ever-Changing

When I first retired, an annual passive income of $80,000 felt like a dream come true. Fast forward to 2015, when my wife joined me in early retirement; our financial landscape shifted dramatically, requiring us to aim for $160,000 to account for her income loss. With the arrival of our son in 2017 and daughter in 2019, our financial demands only increased. Today, paying $2,200 monthly for healthcare and $5,000 for preschool feels overwhelming. The rising cost of living, driven by inflation, means we continually reassess our budget, leading us to acquire more rental properties and invest in resilient assets like healthcare stocks.

The Lure of Traditional Work

Since leaving my corporate job, I’ve often felt the magnetic pull back to traditional employment. The first time I encountered this longing was just six months post-retirement, as I missed the camaraderie of working toward a common goal. The second wave of doubt hit after our son was born; I feared financial instability and the challenges of new parenthood made me think a job could provide a much-needed escape. The final time was during the pandemic, as I observed friends thriving in a balanced remote work environment. Ultimately, I realized that even a flexible job wouldn’t grant me the freedom I craved; I would still be accountable to others.

The Power of Authentic Expression

One of the most liberating aspects of financial independence is the ability to express my thoughts freely. In traditional workplaces, I often felt compelled to hold back, wary of how my words might affect my professional standing. Now, I can share my authentic self without hesitation. For instance, when a producer approached me about narrating my audiobook, I insisted on having a narrator who reflected my identity as an Asian-American. Speaking up ensured that a deserving Chinese-American voice was chosen—a choice I may not have had the confidence to make in a corporate setting.

Legacy Becomes a Guiding Light

With the luxury of time, I’ve found myself reflecting deeply on the legacy I wish to leave behind. Early retirement allows for introspection about what truly matters. For some, that may manifest in scholarships or charitable endeavors, while for me, it’s about empowering others with financial wisdom. Throughout the pandemic, the thought of my children sharing my book during show-and-tell kept me motivated. I’ve learned that nurturing causes that resonate with you, mentoring others, and sharing your blessings contributes to a meaningful legacy.

Shifting from Certainty to Probability

As I navigate this unconventional path, I’ve come to embrace a mindset focused on probabilities rather than absolutes. It’s essential to create as many opportunities as possible for your future self. By saving and investing wisely, you open doors for various life choices, whether that means transitioning to a more meaningful job or enjoying a few years off for family care. My decision-making philosophy centers on a 70/30 approach: if I perceive a 70% likelihood that I’m making the right call, I’m willing to take that leap. I recognize that a 30% chance of error exists, but I view mistakes as valuable learning experiences that pave the way for better choices ahead.

Conclusion: Finding Fulfillment Beyond Traditional Retirement

Reflecting on my decade of “fake retirement,” I’ve learned that fulfillment is not a one-size-fits-all concept. Whether you choose to step away from traditional work or carve out a new path, it’s crucial to prioritize what resonates with you. Embrace the journey, make choices that align with your values, and remember that the beauty of life lies in its unpredictability. After all, it’s not just about retiring; it’s about living fully on your own terms.

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