The Top 7 Retirement Regrets You'd Be Silly Not To Learn From

Retirement is supposed to be your golden years, where you have the freedom to spend your days as you wish, traveling, enjoying hobbies, spending time with family and friends, or simply relaxing. However, according to a recent study from Lincoln Financial, 62% of Americans have regrets about retirement. Two out of 3 retirees who could go back and do things differently.

While it may be too late for them, it may not be for you. Whether you are decades from retirement or thinking of retirement in the next couple of years, their experiences can serve as valuable lessons to learn from. Ignoring them sets you up to make the same mistakes that they did. Regardless of your current financial situation, treating these regrets as an early warning system can help you achieve greater financial peace of mind in retirement.

This article explores seven of the most common regrets that retirees have. Think of it as a roadmap that you can follow to give you a more secure future. Your future self will thank you.

The number one regret of retirees is not saving enough during their working years. In one study, 86% of retirees said that they wished they had saved more money, and 60% wished they had started investing earlier in their lives. In a 2024 Nationwide Retirement Survey, 76% said the single best advice they'd give their younger selves was to save or invest more, and to start earlier. Another survey from TransAmerica found that 76% of retirees wish they had saved more consistently.

They thought Social Security benefits would cover most of their needs, but this often isn't the case. Rising prices, longer lifespans, and unexpected costs can stretch the budget. The biggest mistake comes from waiting too long to start. Those who save even a small amount early in their lives benefit from compound interest, often referred to as the 8th wonder of the world, when your money earns money and then that new money also earns money. It's like a snowball rolling down a hill growing larger and larger.

For instance, if you begin saving $200 a month at age 25 and earn 10.5% interest, by the time you reach 65, your nest egg will grow to more than $1.2 million. But if you wait until age 35 to start, you'll need to save nearly three times as much, about $600 a month, to end up with roughly the same amount. The lesson here is to start saving as soon as possible. Use retirement accounts like 401(k)s or IRAs to take advantage of tax benefits. Use catch-up contributions to make up for lost time. Even if you're older, it's never too late to save more. The best time to invest may have been in the past, the second-best time is today.

37%, almost two out of five retirees, say they regret claiming Social Security too early, per Hartford Funds. You can begin claiming Social Security retirement benefits as early as age 62 and as late as age 70. The age you choose to start taking benefits impacts the amount you receive. Starting before your full retirement age (FRA), which falls between 66 and 67 depending on your birth year, means your monthly payments are permanently reduced. Waiting to claim at 70 can mean receiving 24% more in benefits and 76% more than claiming at 62.

• Claiming at 62: maximum monthly benefit of $2,831
• Claiming at 70: maximum monthly benefit of $5,108

People often underestimate how long they will live. If you live into your 80s or 90s, those bigger checks can make a huge difference. Retirees who claimed early often say they wish they had waited, especially when medical bills or inflation cut into their budgets. The lesson is to create a financial plan and run the numbers before making a decision. Look at your health, family history, and how much you have saved. If you can afford to wait, delaying Social Security can give you more financial freedom later. Think of it as insurance against outliving your savings.

Healthcare costs surprise many retirees. Medicare doesn't cover everything, and out-of-pocket expenses add up quickly. According to a Fidelity survey, 15% of the average retiree's expenses are healthcare costs and 4 out of 10 retirees say that healthcare costs are higher than expected. A couple retiring at 65 may spend hundreds of thousands of dollars on healthcare over their retirement. Many assume that Medicare would cover most expenses, only to discover gaps later. Others regret not budgeting for dental, vision, or prescription drugs, which Medicare doesn't fully cover.

Long-term care is one of the biggest worries for retirees. Data from Lincoln Financial, reported by Morningstar, found that 82% say they're concerned about how they'll pay for it, and nearly half (42%) admit they're highly concerned. However, only 21% have ever discussed long-term care planning with a financial professional, and just 14% have talked about long-term care insurance. Most people will need some form of care, whether at home or in a facility. Without planning, these costs can drain savings fast. Nursing homes can cost more than $127,000 a year.

The lesson is to plan for higher healthcare costs in retirement. Use a tax-advantaged Health Savings Account (HSA). If you are enrolled in a high-deductible health plan, an HSA is a powerful tool. Contributions are tax-deductible, savings grow tax-free, and withdrawals for qualified medical expenses (including many Medicare premiums) are tax-free. At age 65, you withdraw funds for any purpose (subject to income tax, like a traditional IRA). Also look into getting supplemental health insurance, long-term care coverage, or hybrid life policies that help pay for care. Planning now protects your savings later.

Some retirees depend on only one source of income, like Social Security or a pension plan. This leaves them vulnerable when the cost of living increases or unexpected expenses come up. Retirees who have built multiple income streams, such as different types of investment accounts, rental income, or part-time work, feel more secure. Even small amounts of income from different sources can provide extra stability.

For example, dividends from stocks or income from a side business can cover unexpected expenses. Instead of using only a 401(k), using a Roth allows you to make after-tax contributions and take distributions tax-free. A National Bureau of Economic study found that 26% of retirees regretted not having purchased lifetime income payments, such as an annuity. Certain annuities provide a guaranteed income stream that won't run out, regardless of how long the individual lives.

The lesson is not to put all your eggs in one basket. Build a mix of income streams that can handle high inflation, market changes, and unexpected expenses. Even part-time consulting or freelance work can make a difference. Think of diversification as a safety net that keeps you steady when one stream of income falls short.

Recent LIMRA research found that only 1 out of 5 retirees has a formal retirement plan. They assumed that their savings would last or that they could handle any unexpected expenses. Additionally, many retirees spent too much in the early years of their retirement and had to cut back on spending later. They didn't have a budget to help balance lifestyle goals with long-term needs.

One of the most effective steps toward a secure retirement is creating a formal, written financial plan. A plan provides structure, keeps you aligned with your goals, and offers peace of mind as you move closer to retirement. It also reduces stress because you know where your money goes. Without a plan, retirees often feel anxious and unprepared. The research found that only 87% of those with a formal written plan feel confident about living the retirement lifestyle they want. Even those with only an informal plan report higher confidence, at 70%. 

The lesson is to create a written budget before you retire and make sure you continue to update it while in retirement, so you don't overspend. Be sure to include the top retirement living costs such as housing, healthcare, long-term care costs, travel, and everyday expenses. Give yourself a buffer to plan for inflation and unexpected costs. A financial plan gives you greater control and confidence.

Everyone has an opinion on what financial steps you should take. The key is getting the right advice. Most Americans say that working with a financial advisor would give them greater confidence and help them reach their financial goals, however, less than half work with one. Many retirees regret not working with a financial advisor. They tried to handle their finances on their own but ended up making mistakes, missing important tax and estate planning strategies, as well as missed investment opportunities. Working with a professional financial advisor can make a significant difference in achieving long-term financial security. 

Advisors provide customized strategies that align with your goals, risk tolerance, and timeline, helping you find the best investment choices. They take a holistic view of your finances, considering not just investments but also taxes, insurance, retirement accounts, and estate planning. One of their most valuable roles is helping you avoid making rash decisions, such as panic selling during downturns or chasing risky trends. A Vanguard study found that working with a professional advisor can add 3% in net annual returns through smarter portfolio construction, disciplined rebalancing, and implementing the right tax strategies.

The lesson is not to go it alone. A financial advisor, particularly a fee-based one with a fiduciary duty to their clients, can help you avoid costly mistakes. They can help you create a formal financial plan that can provide you with financial peace of mind. Even a few sessions with a professional can uncover ways to save money and protect assets.

Money isn't everything. It's also about finding purpose and meaning in life after work. A MassMutual Study found that many retirees are caught off guard by the emotional transition, experiencing depression, anxiety, health declines, or even marital strain when they don't plan for how to spend their time. Retirees without structure or social engagement often struggle, while those who set personal goals, maintain routines, volunteer, continue learning, and stay socially connected report greater fulfillment.

Retirement can last 30 years or more, making it essential to plan for both financial security and mental health. Practical strategies include creating a daily routine, sharing knowledge through mentoring, focusing on health, reconnecting with a spouse, or even starting a side hustle.

The lesson is to live intentionally by pursuing passions, cultivating relationships, and adopting a growth mindset. Work provided structure and meaning, and without it, retirees may struggle with loneliness, boredom, or a lack of fulfillment. Planning mentally and emotionally for retirement is just as important as financial preparation. Find what gives you purpose and meaning in life. This will help you transition to your new lifestyle in your golden years, ensuring both financial security and a deeply meaningful life.