8 retirement regrets and how to avoid them

Tina Fey by Tina Fey | October 14, 2025, 3:20 pm

Retirement is a significant phase of life, but it’s not without its potential pitfalls.

Have you ever wondered what you might regret when you reach this stage? It’s easy to let crucial details slip while we’re busy dreaming about endless free time and no work emails.

In this article, we’ll be exploring the eight common retirement regrets and, more importantly, how to avoid them.

So if you’re keen on sidestepping these common missteps and ensuring a worry-free retirement, keep reading. I promise you it will be time well spent.

1) Not saving early enough

One of the biggest regrets that many retirees have is not starting to save for retirement early enough.

The magic of compound interest is such that the earlier you start saving, the more your money grows. It’s just simple math. But amidst the hustle and bustle of life, saving for retirement often takes a backseat.

You might think there’s plenty of time left, or you might prioritise other financial needs. But let me tell you, time flies faster than you think.

And once you reach retirement, there’s no going back. You can’t turn back time to start saving earlier.

So if you want to avoid this common regret, start saving now. Even a small amount can make a big difference in the long run.

Remember, it’s never too early to start planning for your retirement. But it can certainly be too late.

2) Ignoring health concerns

Another regret that often plagues retirees is not taking care of their health when they had the chance.

I remember my Uncle Joe, always the life of the party, never one to miss a barbecue or a late-night poker game. But when it came to his health, it was a different story. He was always pushing off doctor’s appointments and ignoring minor ailments, saying he’d take care of it ‘next week’.

Fast forward to his retirement, those minor ailments had turned into major health concerns. He spent most of his time and savings on medical bills and treatments. His retirement wasn’t about leisure and relaxation as he had dreamt; instead, it became a constant battle with his health.

It’s easy to get caught up in the present and ignore those niggling health issues. But trust me, your future self will thank you for taking care of your health now.

So take the time to invest in your health. Regular check-ups, a balanced diet, and physical activity can go a long way in ensuring a healthy and happy retirement.

3) Neglecting to diversify investments

When it comes to investing for retirement, putting all your eggs in one basket can lead to serious regret later on. It’s all about balance.

Did you know, according to a report by the Employee Benefit Research Institute, almost 7 out of 10 workers are confident they have enough money for a comfortable retirement? Yet, the same study reveals that only 4 out of 10 have actually tried to calculate how much money they will need in retirement.

In the world of investments, diversification is key. It helps spread the risk across different asset classes and can provide a safety net if one investment doesn’t perform well.

So, don’t just rely on a single investment or savings plan. Explore different investment avenues like stocks, bonds, mutual funds or real estate. And if investment jargon confuses you, don’t hesitate to seek professional help.

Remember, diversification is not just about having different investments; it’s about having the right mix of investments that align with your retirement goals and risk tolerance.

4) Underestimating expenses

A critical mistake that many retirees make is underestimating their expenses in retirement.

It’s easy to assume that your expenses will decrease once you retire. After all, you won’t have commuting costs or the need for a work wardrobe. But have you considered the costs that might increase?

Take healthcare, for example. As we age, our health needs tend to increase, and with it, the associated costs. Then there’s inflation, which can significantly impact the purchasing power of your savings over time.

To avoid this regret, it’s crucial to plan a realistic retirement budget. Factor in all potential expenses, including healthcare, travel, hobbies, and inflation.

Remember, it’s always better to overestimate your expenses and be pleasantly surprised than to underestimate them and be caught off guard. It’s not just about saving for retirement; it’s also about planning how you’ll spend in retirement.

5) Overlooking the importance of social connections

It’s easy to focus solely on the financial aspects of retirement. But money isn’t the only thing that determines a fulfilling retirement.

I’ve seen it time and time again, retirees who have diligently saved and planned for their financial future, only to realize that they’ve neglected their social life.

Retirement often means losing daily interactions with colleagues and a sense of purpose that work provides. This can lead to isolation and loneliness if not addressed.

So, while you’re planning for your financial future, don’t forget to nurture your relationships and social connections. Join clubs, volunteer, take up a hobby that involves others – make sure you have a social network outside of work.

Remember, retirement is not just about leaving work behind; it’s about embracing a new phase of life full of possibilities. And a robust social life can play a significant role in making this transition smooth and enjoyable.

6) Failing to plan for long-term care

Long-term care is often a topic we’d rather not think about. It’s not pleasant to imagine needing help with daily activities or having a chronic illness. But ignoring it doesn’t make it go away.

My grandma used to say, “I’ll cross that bridge when I come to it,” when we’d bring up the subject of her future care. She insisted she was fit as a fiddle and didn’t need any long-term care planning.

Sadly, a sudden stroke left her dependent on others for basic tasks. The lack of planning not only put a financial strain on our family but also caused unnecessary stress and anxiety.

When planning for retirement, it’s essential to consider potential long-term care needs. Look into long-term care insurance or include these costs in your retirement savings plan.

Remember, planning for the worst doesn’t mean you’re wishing for it; it just means you’ll be prepared if it happens. As the old saying goes, “Hope for the best, but prepare for the worst.”

7) Postponing dreams and aspirations

Retirement is a golden opportunity to pursue dreams and aspirations that may have taken a backseat during your working years. Unfortunately, many retirees regret not seizing this opportunity sooner.

It’s common to think, “I’ll do that when I retire,” whether it’s traveling the world, learning a new skill, or starting a small business. But how often do we actually follow through?

Retirement can be a fulfilling and exciting phase if you make the most of it. Start mapping out your retirement dreams now. What are the things you always wanted to do but never had the time for?

Remember, it’s not just about surviving retirement; it’s about thriving in it. Don’t wait until it’s too late to start living your dreams. After all, retirement is a journey, not a destination.

8) Forgetting that retirement is a major life transition

Retirement is more than just an end to work; it’s a significant life transition. It can bring a whirlwind of emotions, changes, and adjustments. And the regret that many retirees have is not acknowledging this fact.

Retirement can impact every aspect of your life, from your daily routine and social connections to your sense of purpose and identity. It’s essential to prepare for these changes mentally and emotionally, not just financially.

Remember, the key to a successful and happy retirement lies in embracing it as a new phase of life, full of opportunities to learn, grow, and enjoy.

Final thoughts: Retirement is more than just a phase

Navigating the retirement journey is no easy task. It’s a significant life transition that comes with its fair share of potential regrets.

But the beauty of it is that these regrets can be avoided with good planning, foresight, and a bit of wisdom.

Remember, retirement is not the end of the road; it’s just a new path. It’s your time to enjoy the fruits of your labor, pursue passions, and create a life that’s fulfilling and rewarding in its own way.

So whether you’re on the brink of retirement or it’s still a distant thought, consider these common regrets and how to avoid them. Because ultimately, retirement should be about living your best life, free from regret.

As George Foreman once said, “The question isn’t at what age I want to retire, it’s at what income.” So plan wisely, live well, and make every moment count.

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