As a member of the baby boomer generation, and specifically someone born during its later years, I recognize that I still have several remaining years of employment ahead of me before the prospect of retirement becomes a tangible reality. As I observe the growing number of friends, relatives, and peers from my generation who are now gracefully stepping into their retirement years, I find myself increasingly preoccupied with serious reflection on what my own future may hold. I cannot help but question whether the decisions I made throughout my life were sufficient to create the level of financial security necessary for a stable and comfortable retirement. At the same time, there are moments when I look back and critically examine the choices I embraced—wondering whether they were truly made with foresight or simply with the desire to seize the moment without fully considering long-term consequences.
A vivid example of this comparison presents itself in my own family: my brother, who recently transitioned into retirement, provides a clear contrast to my situation. He has managed to accumulate a substantial financial safety net, the result of years of consistent and disciplined effort. Beginning his working life at the age of sixteen, he wisely aligned himself early on with a union that provided not only reliable employment but also a structured system of benefits. Watching his current financial stability and his ability to embark on the next life chapter with confidence triggers in me a strong sense of envy, particularly as I continue to manage the pressures of work while grappling with my own financial challenges.
In contrast, when I was younger, I prioritized my personal aspirations and creative dreams over conventional financial stability. My career began at age seventeen when I entered full-time employment immediately after graduating from high school. Yet, during one of my earliest paid vacations, I traveled abroad and developed a profound fascination with Italy. That experience ignited within me an enduring goal: to immerse myself in Italian culture and ultimately find a way to live and work there. Throughout my early twenties, my dedication to this dream led me to accept intermittent jobs, working only enough to sustain myself while continuing my pursuit of a life in Italy. When it eventually became clear that securing regular employment abroad would be extraordinarily difficult, I redirected my efforts by seeking academic opportunities, applying successfully to a university in Rome.
Through financial assistance in the form of a family loan, coupled with employment at the university itself, I managed to pay tuition and academic expenses. After two years of study, I obtained an associate degree, and rather than returning home immediately, I chose to remain in Rome for an additional two years. During this period, I secured full-time work at the university, further deepening my immersion in both the Italian language and lifestyle. These years became defining experiences in my life, broadening my worldview, even though they were not advancing my financial stability in the ways that traditional career choices might have.
Eventually, after four years of living and working abroad, I returned to the United States. What followed was a series of transitions as I searched for professional direction until I discovered a career path within the trade show industry. As an Operations Manager, I thrived for over a decade at the same organization, a period marked by extensive travel and a career that suited my independent, adventurous spirit. Yet, despite this stability, I made an error that, in hindsight, significantly affected my future: I failed to contribute to my employer’s 401(k) retirement plan until my fifth year there, by which time I was already in my late thirties. At that time, my focus was firmly on enjoying career achievements, the excitement of travel, and the pleasures of a single life, rather than dutifully laying the groundwork for eventual financial security. It was during this chapter, however, that I first connected with a financial advisor, who has since remained an invaluable guide as I have changed positions and consolidated different retirement accounts.
Although I continue to contribute diligently to my current 401(k), I cannot escape the unease that my savings will fall short of sustaining a worry-free retirement. Remaining single and without children, I had long assumed that this would simplify my financial responsibilities, since I would only need to consider my own needs. Yet the economic reality has proven more challenging. After company downsizing and personal burnout forced me to leave the trade show industry, I transitioned into a job in wine retail, an area of genuine personal interest to me. While I steadily advanced to the role of store manager, the move involved a dramatic reduction in income. Thus, despite my commitment, passion, and management responsibilities, the financial strain of lower earnings left me living paycheck to paycheck. The absence of a second household income or additional side earnings has intensified this sense of precarity.
Looking back, I also acknowledge a major financial decision that still occupies my thoughts: I chose never to purchase property, preferring instead the flexibility of renting. In my younger years, this choice felt liberating because I valued the freedom to relocate without being bound by the long-term commitments of homeownership. Even now, that mobile, adventurous mindset still resonates with me. Yet, as I approach retirement, I often find myself questioning whether that choice deprived me of an asset that could have strengthened my financial foundation. In an effort to improve my current trajectory, I have once again sought guidance from my financial advisor, who, fully aware of my circumstances, strongly recommended that I increase contributions to my existing 401(k). To create the financial space necessary to do this, I recently moved into a 55+ community located farther from my workplace, a decision that substantially reduced my living expenses and freed up cash to direct toward retirement planning.
When I reflect deeply on this journey, I recognize a mixture of regrets and affirmations. I regret not beginning a 401(k) earlier, since every year of lost compound growth represents a missed opportunity to enlarge my retirement savings. If I had prioritized contributions in my twenties, I might now be significantly more comfortable. Yet, I cannot regret my time in Italy—it remains one of the most enriching chapters of my life and continues to shape who I am. In fact, when I learned that an acquaintance of mine, now retired, plans to relocate to Portugal, it rekindled my own aspiration to potentially spend my later years back in Italy. As for my decision against property ownership, I rationalize it as consistent with my lifelong inclination for flexibility and exploration, even though I occasionally wonder whether this same desire for independence is responsible for my single lifestyle as well.
Ultimately, my story reflects a broader struggle familiar to many in my generation: the difficulty of balancing dreams, independence, and spontaneity with the discipline and foresight required for long-term financial security. Now, as I reconsider what retirement may look like, I do so with both apprehension and hope, carrying the memories of choices made alongside the determination to improve the path that still lies ahead.
Sourse: https://www.businessinsider.com/boomer-living-by-paycheck-cant-retire-regrets-2025-9
