5 Retirement Regrets You'll Want to Avoid – Plan Smart, Retire Happy

Discover the top 5 retirement regrets retirees face and learn how to proactively plan your financial future. Avoid common mistakes and secure a comfortable, worry-free retirement.

Mike Upland

4/26/20252 min read

a man sitting on a couch with his hand on his chin
a man sitting on a couch with his hand on his chin
5 Retirement Regrets You'll Want to Avoid

Approaching or enjoying retirement? You're not alone if you're wondering how to avoid the most common financial missteps. According to a 2024 Transamerica Center Study, 76% of retirees wish they had saved more consistently. Today, we'll explore the top retirement regrets and how you can sidestep these pitfalls for a worry-free future.

Regret #1: Not Saving Enough, Soon Enough

Many retirees lament not starting their savings journey earlier. Retirement can feel distant when you're young, making it easy to de-prioritize. Lack of financial education further complicates early investment decisions. Time in the market is crucial—early investments grow exponentially due to the power of compounding. Start educating the next generation early to break this cycle.

Regret #2: Underestimating Retirement Expenses

A common misconception is that expenses decrease post-retirement. However, the "go-go" years—when retirees are active and travel—often lead to higher spending. According to Fidelity, retirees should anticipate spending between 55-80% of their pre-retirement income annually. Planning for hobbies, travel, and unexpected expenses is essential.

Regret #3: Not Planning for Healthcare Costs

Healthcare expenses are a significant financial burden in retirement. Fidelity's 2024 estimate indicates that a 65-year-old retiree should expect to spend around $165,000 on medical costs—even with Medicare. Early retirees feel this pinch even more before Medicare eligibility. Including healthcare in your retirement plan is non-negotiable.

Regret #4: Relying on Just One Source of Income

Depending solely on Social Security can be risky. Diversify your income streams through dividend-paying stocks, rental properties, REITs, or part-time work. Multiple sources offer not just financial security but also peace of mind.

Regret #5: Not Seeking Professional Financial Advice

Navigating retirement planning alone can lead to costly oversights. Financial advisors help factor in rising healthcare costs, inflation, and unforeseen expenses. Professional validation of your strategy boosts confidence and ensures a more robust financial future.

Conclusion

The underlying theme across these regrets is the importance of proactive, diversified financial planning. Early investment, realistic expense forecasting, healthcare planning, income diversification, and professional advice form the pillars of a successful retirement.

FAQs

Q1: What is the best age to start saving for retirement? The earlier, the better. Starting in your 20s maximizes compounding benefits.

Q2: How much should I plan to spend annually in retirement? Expect to spend 55-80% of your pre-retirement income, depending on your lifestyle.

Q3: How can I diversify my retirement income? Invest in stocks, real estate, REITs, and consider part-time work.

Q4: Are healthcare costs covered entirely by Medicare? No, retirees still face significant out-of-pocket healthcare costs, averaging $165,000 over retirement.

Q5: Why should I hire a financial advisor for retirement planning? An advisor can help you foresee potential pitfalls, validate your plan, and adapt to economic changes.

Watch the video on this topic here for even more information and detail!