5 Retirement Mistakes People Turning 65 Regret the Most

Turning 65 is a milestone — a time for reflection, celebration, and planning the next exciting chapter. But for many, it’s also the moment when overlooked financial missteps and planning oversights come into sharp focus. Whether you're nearing retirement or supporting a loved one who is, avoiding common mistakes can save you from serious regret down the road.

Here are the five biggest retirement mistakes people wish they had avoided — and how you can learn from them.

1. Claiming Social Security Too Early

One of the most common regrets? Starting Social Security benefits as soon as they become available. While it’s tempting to begin claiming at 62, doing so could permanently reduce your monthly benefit by up to 30%.

Waiting until your full retirement age (typically 66 or 67), or even delaying until 70, can significantly increase your monthly payments — and for many, this added income makes a big difference in the long run.

Avoid the regret: Calculate your break-even point, consider your health and family longevity, and work with a financial advisor to find the right claiming strategy.

2. Underestimating Healthcare Costs

Medicare doesn’t cover everything. Many retirees are surprised by out-of-pocket expenses like premiums, deductibles, dental, vision, and long-term care.

The average 65-year-old couple retiring today may need over $300,000 to cover healthcare expenses throughout retirement. And that doesn’t include unexpected health emergencies.

Avoid the regret: Factor healthcare costs into your retirement budget. Consider Medigap or Medicare Advantage plans, and don’t overlook long-term care insurance if it fits your needs.

3. Failing to Create a Retirement Income Plan

Many people focus on building a nest egg — but not enough think about how to turn it into steady income. Without a clear plan, retirees often overspend early or under-spend out of fear, neither of which leads to peace of mind.

Avoid the regret: Develop a diversified income plan that combines Social Security, pensions, annuities, and withdrawal strategies from your savings. Aim for a sustainable drawdown rate and revisit it annually.

4. Not Adjusting Lifestyle Expectations

Retirement brings a new rhythm to life — but not everyone adjusts their spending accordingly. Many people regret not downsizing sooner, maintaining expensive habits, or failing to cut back in ways that reflect their new income reality.

Avoid the regret: Take an honest look at your lifestyle and expenses before retiring. Downsizing, relocating, or simply rethinking what brings you joy can help align your lifestyle with your financial reality — without feeling deprived.

5. Neglecting Estate Planning

It’s uncomfortable to think about, but essential. Many retirees regret putting off estate planning or assuming a basic will is enough. Without the right documents and conversations, your legacy — and your loved ones — could face legal headaches, taxes, or family conflict.

Avoid the regret: Have a solid estate plan in place, including a will, healthcare directive, and financial power of attorney. Review beneficiary designations regularly, and talk openly with your family about your wishes.

Final Thoughts

Retirement isn’t just a financial shift — it’s a life transition. The key to a fulfilling, regret-free retirement is proactive planning, honest self-assessment, and seeking guidance when you need it.

If you’re approaching 65, take this moment to pause, plan, and prepare. Your future self will thank you.