Hitting your 60s should be the point where you finally get to put your feet up, but it’s often when you look back and kick yourself over old money choices.
When you’re younger, retirement feels so far off that it’s easy to push pension talk down the to-do list, or assume everything will just sort itself out. The reality hits home when you’re actually staring down the barrel of finishing work and realizing those small choices you made decades ago now dictate exactly how comfortable your life is going to be.
It’s not usually about major financial disasters either; it tends to be the everyday habits, the missed opportunities to save, and the sneaky debts that quietly add up over 30 years. The most common financial regrets shouldn’t make you feel miserable about the past—they’re simply a wake-up call that shows exactly how to protect your cash while you still have the time to fix it.
Handing over too much money to grown-up children
Helping your children, even when they’re adults, feels like the natural thing to do, especially with house prices and student debt making life harder for younger generations. But a lot of parents give away more than they can really afford, and only notice the gap once it’s too late to fill it. Research from St James’s Place found that a quarter of parents expect to dip into their own retirement savings to support their children, and nearly a third think they’ll have to delay retirement because of it.
The fix isn’t to stop helping altogether. It’s to slow down. Give a smaller amount now, then check your own finances again in a few years before deciding whether you can give more. That way, you’re not promising money you might need for yourself later.
Putting off the holiday until “someday”
So many people spend their 50s and early 60s saving hard for retirement, only to find that by the time they get there, their health or energy has changed. One financial planner said he’s seen cases where illness, or worse, arrived before someone got the chance to enjoy the money they’d spent decades building up.
You don’t have to choose between saving for later and living now. A financial planner can run the numbers and show you whether that big trip or dream purchase would actually put your future at risk, or whether you’ve been more cautious than you needed to be. Often the answer is that you had more room than you thought.
Staying in a safe job for too long
A stable job feels like the sensible option, and in the moment it usually is. However, research from JP Morgan Personal Investing found that almost a third of people in midlife regret staying in work that didn’t fulfil them, and around a fifth wish they’d changed career or retrained sooner.
The main thing stopping people switching is money. Retraining costs, and dropping down in salary while you start again can feel impossible to plan for. Building a savings buffer before you make the leap gives you room to take that risk without it wrecking your finances.
Keeping everything in cash
Cash feels safe because you can see it and it doesn’t go up and down. The trouble is, inflation quietly eats away at its value every year, even while the number in your account stays the same. One adviser put it plainly: holding too much cash is one of the main reasons people miss out on the retirement they’d hoped for.
Even people who do invest sometimes play it too safe, sticking only to low-risk options that barely outpace inflation. It’s worth checking your investments now and then to see if your attitude to risk still matches your plan, especially as pensions often transition automatically towards lower-risk options as you get closer to retirement. If that change happens too early, it can quietly limit your growth for years.
Waiting far too long to think about inheritance tax
Plenty of people spend years worrying about how to pass money on to children and grandchildren, then discover in their 60s or 70s that a chunk of their estate will be lost to inheritance tax that could have been avoided with earlier planning. It’s one of the most common regrets lawyers and advisers hear.
Inheritance tax receipts are actually forecast to rise sharply over the coming years, which makes the case for planning ahead even stronger. The earlier you start, the more options you have. Waiting until your later years narrows the choices considerably.
Not making use of the seven-year gift rule sooner
Here’s one that catches a lot of people out. If you give money away and survive seven years afterwards, it usually falls outside your estate for inheritance tax purposes. But many people put off making gifts because they’re not sure they’ll live that long, only to realise a decade later that they would have survived the seven years easily, if only they’d started the clock sooner.
By then, they’re older and the odds of surviving another seven years have changed again. It becomes a cycle of putting things off. You don’t need to give away everything at once. Even using your annual gift allowance, or gifting from surplus income you don’t need for everyday life, can chip away at a future tax bill without affecting how you live now.
Never quite getting around to writing a will
It’s an easy thing to keep putting off because thinking about your own death isn’t exactly a fun way to spend an afternoon. But more than a fifth of people aged 65 and over in the UK don’t have a will, according to the Money and Pensions Service. That leaves basic decisions, like who looks after the family pet or how savings get split, entirely up to chance.
Without a will, loved ones can end up dealing with extra stress, extra costs and sometimes arguments at exactly the moment they’re grieving. Sorting out a will, and a lasting power of attorney alongside it, takes far less time than most people expect, and it removes a huge amount of uncertainty for the people you leave behind.
Learning from these regrets sooner rather than later
What stands out across all of these regrets is that none of them come from one big mistake. They build up slowly, through small delays and understandable caution, until suddenly a decade or two has passed. The good news is that every one of these situations can still be improved no matter what age you’re starting from. A conversation with a financial adviser, a bit of honesty about how you actually want to spend your money, and a will sitting somewhere safe can make all the difference to how the next chapter goes.
