Picture yourself 10 or 15 years from now. Your working days are behind you, and mornings move as slowly as you like. It’s the retirement you pictured — or at least, it should be. But instead of feeling content, this stage of life can bring a surprising sense of regret for many retirees. They wish they’d saved more, planned earlier, or thought harder about how they’d actually spend their days.

The truth is, retirement can be deeply rewarding — but only if you prepare for it. Many retirees look back and admit they’d do things differently if they had their time again. The good news? You don’t have to repeat their mistakes.

In this article, we’ll explore the 9 most common retirement regrets — and show you the practical steps you can take now to steer clear of them.

Prefer watching? This video breaks down the same topic:

The top regrets of the retired

When you ask Australian retirees what they’d change, the same themes come up again and again. Let’s unpack the 9 most common regrets of the retired so you can avoid them.

1. I retired too late (or I worked for longer than I needed to)

Many retirees stay in the workforce longer than necessary. Sometimes it was the fear of running out of money. Other times it was simply habit – work had become part of their identity. But those extra years came at a cost: missed chances to travel, spend time with family, or simply enjoy life.

How to avoid it:

• Get clear on your financial position well before you retire.
• Use retirement modelling to see whether early retirement is feasible.
• Don’t wait for someone else to tell you it’s “time”. Instead, make a plan that lets you retire on your own terms.

Deciding when to retire isn’t always simple. From finances to fulfilment to health, there’s a lot to weigh up. Learn more in our article How Do You Know When To Retire? 8 Signs It Might Be Time.

2. I didn’t get financial advice

Many retirees admit they “played it by ear” when it came to retirement planning. And what happens when you rely on guesswork instead of professional advice? You miss opportunities to increase your savings, trigger unnecessary tax penalties, and overlook pension strategies that could’ve boosted your income. For some, this meant retiring later than they needed to, or running into cash flow stress they could have avoided.

How to avoid it:

• Have a clear understanding of your retirement goals such as when you plan to retire, how much you’ll spend each year, and any big one-off expenses you’ll face.
• Seek professional advice, especially in the final years leading up to retirement, to ensure your goals are realistic and achievable.

A good adviser will also review your super and investments, keep you across contribution and pension rules, and run projections so you know your strategy will hold up over time — all while optimising your position and helping you avoid costly missteps.

3. I retired too early … and my savings didn’t last

For some retirees, the dream of early retirement turned sour when their savings dried up faster than expected. They underestimated how much money they’d need to fund their lifestyle, and overestimated how far the Age Pension or their super earnings would stretch. Some were caught off guard by an underperforming super fund, leaving them with less than expected.

How to avoid it:

• Use retirement projections to learn how much you can spend each year and how long your savings are likely to last.
• Choose a sustainable withdrawal strategy that supports your goals and budget.
• Consider delaying retirement by just one or two years to boost your super balance and reduce pressure.

4. I didn’t plan for a longer life

Australians are living longer than ever — often 20 to 30 years beyond retirement. Many retirees wish they’d factored this in. They underestimated how long their super would need to last and put off planning for potential aged care needs, leaving them unprepared later in life.

How to avoid it:

• Use conservative life expectancy estimates in your retirement projections — a longer life means more years to travel, enjoy hobbies, and spend with family.
• Factor in the rising cost of living over time, so your lifestyle stays comfortable in later years.
• Understand how the Age Pension can work alongside income streams like an account-based pension to help extend the life of your retirement savings.
• Think in terms of decades, not just years, when building your retirement plan.

5. I misjudged my lifestyle costs

Many retirees are surprised by how quickly unexpected expenses can derail their plans. Retirement expenses can end up higher than expected, and lifestyle aspirations (from travel to hobbies) don’t always match the budget reality.

How to avoid it:

• Budget for how you wish to spend your retirement days. What will your week look like?
• Consider using your super tax-free (post-age 60) to help cover some of these costs.
• Track your current spending and model different retirement scenarios to see how your savings might hold up.
• Factor in one-off expenses, such as travel, home renovations, or financial support for the kids.

6. I didn’t spend enough early in retirement

Another common retiree regret is sitting at the opposite end of the spectrum. While some people misjudge their costs and end up stretched too thin, others are so worried about running out of money that they hold back too much. As a result, they miss out on their healthiest, most active years of retirement when travel, hobbies, and new experiences are easiest to enjoy.

How to avoid it:

• Set aside a spending buffer specifically for the things you want to do while you’re still fit and well enough to enjoy them.
• Use retirement modelling or work with an adviser to map out a safe spending rate, so you can enjoy your early retirement years with confidence that your long-term income is secure.

7. I didn’t have a plan for my days

Retirement isn’t just a financial decision. It’s a complete lifestyle shift. Without the structure of work, it’s easy for days to slip by without direction. Many retirees later wish they’d thought more about how they’d spend their time.

How to avoid it:

• Start building hobbies and social activities into your life now — because research suggests only about 21% of people who just say they’ll take up new activities in retirement actually follow through.
• Consider volunteering, consulting, or easing out of full-time work through a transition to retirement (TTR) strategy.
• Be intentional about creating and maintaining friendships: join clubs, take group classes, or find community through volunteering or local communities.
• Remember, a fulfilling retirement needs both financial and non-financial planning.

8. I neglected my health

True wealth is more than money — and retirees who neglected their health (from fitness and nutrition to preventative care and dental) almost always regret it later. Poor health can limit your ability to enjoy retirement, increase your medical costs, and reduce the time you’re able to stay active and independent.

How to avoid it:

• Stay active, eat well, and schedule regular medical check-ups.
• Account for health-related expenses within your retirement budget. These might include private health insurance premiums, future aged care costs, and activities that support your overall wellbeing.
• Remember, maintaining your health isn’t just about living longer — it’s about making sure those years are lived on your terms, with freedom and quality of life.

For more practical planning on keeping health costs under control in retirement (like what Medicare covers, potential out-of-pocket costs, and concession eligibility), see MoneySmart’s guide on managing health costs in retirement.

9. I delayed estate planning

Not having an up-to-date will or a tax-effective estate plan can leave your family dealing with unnecessary stress, confusion, and costs. Without clear instructions, assets may not be distributed the way you intended, and your loved ones could face delays or even disputes during an already difficult time.

How to avoid it:

• Start estate planning early and review it regularly, especially after major life events like marriage, divorce, or the arrival of grandchildren.
• Work with a professional to ensure your will, superannuation beneficiary nominations, and ownership structures are current, clear, and tax-efficient.
• Think beyond just the money — estate planning also helps protect your family, ensures your wishes are carried out, and provides peace of mind that everything is organised.

Plan now to avoid regret later in life

The best retirement is one you don’t regret.

Start planning now to avoid common retiree regrets and create a retirement that’s financially secure, fulfilling, and enjoyable. From your finances and health to how you spend your days and connect with others, the choices you make today give future you the chance to thrive.

At Toro Wealth, we help Australians in their 50s, 60s and 70s plan for a secure retirement with clarity and confidence. Book your initial consultation with us and take the first step towards a retirement you won’t regret.

FAQs on common retirement regrets

Here are some of the most frequently asked questions about retiree regrets.

1. What do retirees regret the most?

Most retirees regret not planning ahead, especially around finances, lifestyle goals, and how they’ll spend their time.

Careful retirement planning and financial advice can help you avoid these common regrets.

2. Is retiring early a mistake?

Retiring early can be a mistake if you’re not financially and emotionally prepared.

Early retirement means self-funding more years, so your superannuation, investments, and spending habits must be well planned. You should also have a plan for how you’ll stay active, fulfilled, and connected with others.

3. How can I avoid regrets after I retire?

You can avoid regrets by planning well ahead of retirement.

Create a financial strategy that covers your superannuation, investments, healthcare, and lifestyle goals. Working with a financial adviser can help you make informed decisions.

Beyond financial security, you should think about what’ll give your days meaning and keep you socially connected (e.g., hobbies, travel, volunteering, part-time work).

4. Is it worth seeing a financial adviser before retirement?

Yes — a financial adviser can help you grow and manage your super, create tax-effective income strategies, avoid costly mistakes, and structure your retirement income so you feel confident about the future.

5. How long should I plan for in retirement?

You should plan for at least 25-30 years in retirement.

Australians are living longer than ever, so it’s important to make sure your savings and investments can support you for the rest of your life.

Your retirement income plan should also account for inflation, your current health status (and family medical history), potential aged care deposits, and other future healthcare needs.

6. What can I do if I already regret my decision to retire?

If you regret retiring, consider returning to part-time work, joining a community group, reviewing your spending, or seeking advice to restructure your investments.

Ultimately, the best next step for you depends on the root cause of your regret. So, take time to reflect on what’s missing. Then based on that, choose the action that’ll bring you the most fulfilment and happiness.