The journey to a financially secure retirement is often envisioned as a serene path, free from anxieties. Yet, for many, this vision is clouded by “what ifs” and “if onlys”—regrets stemming from decisions made, or not made, decades prior. Understanding these common financial worries empowers current workers to proactively chart a course toward a more secure future.
Forbes has long championed foresight in financial planning. The experiences of retirees offer invaluable lessons, from impulsive lifestyle changes to overlooked strategies. By examining the pitfalls that often lead to financial unease, we can equip ourselves with knowledge to build a robust foundation, ensuring our golden years are truly golden. Let’s delve into the first few critical imperatives retirees wished they had tackled sooner.
1. **Relocating on a Whim**The allure of a fresh start in retirement, often in a sunnier climate, is powerful. Visions of endless golf or beach strolls are enticing, promising an idyllic post-work life. However, an impulsive move without thorough vetting can quickly lead to regret. New environments might prove less engaging, with unfamiliar surroundings and a slower pace of life quickly losing their charm, transforming a dream into a significant financial and emotional misstep.
Financial experts strongly advise “testing the waters” before a permanent relocation. Extended vacation time in a prospective destination allows for a realistic assessment of the lifestyle, community, and local dynamics. This due diligence is crucial, especially when considering international retirement, where new languages, laws, and customs can be overwhelming. Always assess long-term financial impacts, like rising property costs or expensive flood insurance, and consider renting before purchasing to prevent future distress.
2. **Falling for Too-Good-To-Be-True Offers**A secure retirement is built on diligent work, meticulous planning, and decades of strategic wealth accumulation; there are no legitimate shortcuts. Despite this, Americans consistently lose hundreds of millions annually to get-rich-quick schemes and elder fraud, as reported by the FTC. The rampant nature of credit card fraud, projected to reach $43 billion by 2026, highlights this pervasive and constant threat to retirees’ hard-earned savings.
Vigilance is paramount. Red flags for fraudulent offers include guaranteed spectacular, risk-free profits, requests for upfront fees or wire transfers to claim a prize, or unnecessary demands for sensitive financial information like bank accounts or Social Security numbers. Pressure for immediate decisions or discouragement from seeking impartial advice are significant warning signs. The FTC and state Attorney General offices offer vital resources; always research any suspicious offer and file a complaint if you suspect a scam.
3. **Planning to Work Indefinitely**Many baby boomers anticipate continuing to work beyond 65, whether by choice or necessity, often to maximize Social Security benefits. Fidelity’s 2025 survey indicates over half of workers plan to continue part-time work indefinitely, reflecting a growing trend of gradual retirement. While this strategy appears appealing, it carries inherent risks that can significantly derail even the most carefully laid plans.
Unforeseen circumstances frequently force early retirement. Health-related issues—personal or those of a loved one—are major factors that can unexpectedly remove you from the workforce. Employer-related issues such as downsizing, layoffs, and buyouts can also abruptly end careers, irrespective of an individual’s readiness. Failing to keep skills up to date further complicates this plan. Financial planning should therefore assume continued work might not be an option, emphasizing the critical need for early and consistent savings to ensure true financial security.
The journey toward a secure retirement is fraught with potential missteps, and while the first three regrets we explored focused on external factors and lifestyle choices, the next set delves into core financial decisions. These are the choices that, if made incorrectly, can fundamentally alter the landscape of your golden years. Let’s continue our exploration of the financial worries retirees wish they’d tackled decades before, offering actionable insights for today’s workers.
4. **Putting off Saving for Retirement**One of the most profound regrets for many retirees is having delayed their retirement savings. A 2025 Northwestern Mutual study highlighted this, revealing that a staggering 75% of Americans with retirement savings possess less than one year’s worth of their current income. This trend is particularly alarming for Gen X’ers, many nearing retirement with only three times or less of their annual income saved, underscoring a significant financial preparedness gap across generations.
This procrastination significantly diminishes the potent effect of compounding. Financial experts, like certified financial planner Ajay Kaisth, note that aggressive saving often doesn’t begin until a person’s 40s or 50s. While catch-up contributions are available—such as an extra $7,500 to a 401(k) for those 50+ in 2025, or an additional $1,000 for IRAs—the steep financial climb is undeniable. For example, building a $1 million nest egg by age 65 (assuming an 8% interest rate, 2% inflation, and no prior savings) requires $300 monthly if started at 25, but a formidable $3,000 monthly if begun at 50. This stark contrast underscores the critical value of saving early and consistently.
5. **Claiming Social Security too Early**Claiming Social Security benefits prematurely is another common financial regret among retirees. While eligible to start at age 62, this decision carries a substantial and permanent reduction in monthly payments. Most financial planners advocate waiting until your full retirement age (FRA), which is 67 for those born after 1959, or even delaying until age 70 if feasible, to maximize lifetime benefits.
Opting for benefits at 62, when your FRA is 67, results in a significant 30% reduction that lasts for life. Conversely, delaying beyond your FRA offers a powerful financial advantage: an 8% annual boost in benefits between ages 67 and 70 through delayed retirement credits. Natalie Colley, a financial analyst, compellingly argues, “If you can live off your portfolio for a few years to delay claiming, do so. Where else will you get guaranteed returns of 8% from the market?” This highlights the substantial, guaranteed increase in income that patience provides.
6. **Borrowing from your 401(k)**Taking a loan from your 401(k) can be tempting, as it’s your money and plans often permit repayment over five years with interest. However, financial experts widely view this as a detrimental move, reserving it strictly for dire emergencies. Meghan Murphy, a vice president at Fidelity Investments, highlights critical drawbacks: you’re likely to reduce new contributions and forfeit employer matches—essentially free money. This also means missing out on the compounding investment growth from both the borrowed cash and suspended contributions, significantly impacting your nest egg’s potential.
A major pitfall arises if you leave your employer before repayment: the outstanding balance typically becomes due within 60 to 90 days. Failure to repay results in it being treated as a taxable distribution, incurring ordinary income tax and, if under 59.5, an additional 10% penalty. This double taxation on interest paid, first with after-tax dollars and again upon retirement withdrawal, further diminishes its appeal. Before considering a 401(k) loan, explore alternatives like an emergency fund, Health Savings Account (HSA), or employer stock plan options, which often carry fewer risks. Dedicated loans for college or home repairs are generally preferable to jeopardizing your core retirement savings.
The wisdom gleaned from those who have navigated retirement’s complexities offers a profound blueprint for future financial success. By proactively addressing potential pitfalls—from the allure of quick fixes and premature Social Security claims to the risks of delayed savings and 401(k) loans—we empower ourselves to build a truly secure and fulfilling post-career life. The journey to a financially sound retirement isn’t about avoiding all missteps, but about learning from others’ experiences and applying those lessons with diligence and foresight, ensuring our golden years are not defined by regret, but by well-deserved peace of mind.
