Seven Year-End Money Questions to Ask Before 2027

Most people look at their money in a rush during the last weeks of the year, or not at all. A short, honest review in December can surface problems that are cheap to fix now and expensive to discover in March. Here are seven questions worth working through before the calendar turns over to 2027.

1. Are any of your big financial decisions carrying a hidden tax bill?

Year-end is often when people make the moves that trigger tax. Selling an investment property, realising investment gains, making super contributions and receiving super death benefits can all change how much tax you pay. The timing matters as much as the decision itself.

Take selling a property as an example. Capital gains tax (CGT) may apply, and the sale date can shift your tax position, especially with recent budget changes in the mix. Here's the thing: a sale that looks sensible on the price alone can look quite different once tax is factored in. If you have a large super balance, it's also worth checking whether Division 296 tax could affect you, with the first assessment applying to the 2026–27 financial year.

Before you commit to anything major, map out the tax consequences and ask a tax professional to check the numbers against your own situation. General guidance can point you to the right questions, but it can't tell you what your return will show.

2. Is your super working as hard as it could?

Super is one of the largest assets many Australians build over their working lives, and it's easy to leave on autopilot. If you run a self-managed super fund (SMSF), there's more to keep track of, from investment decisions and running costs to the paperwork that comes with it.

A useful review looks at a handful of areas. Start with the investment mix: does it still match your retirement timeline, your goals and how much risk you can comfortably carry? Then check fees and insurance inside super. Are you paying sensible fees, and does your cover still fit your life? Consider whether extra contributions could help you reach your retirement goals, but confirm your eligibility, the contribution caps and any tax implications before acting.

Two quieter items deserve attention too. Beneficiary nominations often sit untouched for years, and they should still reflect your wishes. If you have an SMSF, ask whether the control it gives you still justifies its ongoing costs and administrative load. Some people find it does. Others discover a simpler structure would serve them better.

3. If you're planning a property move, have you stress-tested it?

Property remains a popular way to build wealth, but the right move depends on your finances and goals, not on headlines. Buying an investment property adds a loan and ongoing costs that can crowd out saving, investing and other goals. Before taking on new debt, look at your existing commitments and cash flow with a mortgage broker who can assess your borrowing options.

If you already own investment properties, pull up the numbers. Rental income is only one line. Subtract loan repayments, maintenance, insurance and vacancy periods, and you'll often see a clearer picture. Some properties carry their weight comfortably. Others quietly drain cash every month.

Retirement changes the calculation. If you're getting close, ask whether holding a property still supports your plans, or whether selling could release capital you'd rather have in hand. Selling is a big decision with its own costs, so it's worth modelling both paths side by side.

4. Is too much of your wealth riding on one bet?

Concentration is easy to miss. If most of your net worth sits in a single property, or your shares cluster in one industry or one region, your finances are more exposed to a downturn in that area than you might realise. Add up your holdings across everything, including super, and see where the weight really lands.

Timing matters as much as spread. Money you'll need within a few years, such as funds for a child's education, belongs in a setting that suits that timeframe, not in investments that could swing sharply just before you need them. Your overall strategy should reflect your goals, your timeline, your comfort with risk and how easily you need to reach your funds. That last part is the one people most often skip.

5. Have you decided how you'll transition into retirement?

Retirement doesn't have to be a switch you flip on a single day. Some people gradually cut their hours, while others step straight into full retirement. Each path has different effects on income, super access and day-to-day cash flow, so it helps to decide early.

Planning goes beyond the super balance. Your family home, investment properties, other savings, family responsibilities and the lifestyle you want all factor in. Ask whether your existing assets can produce the income you need, whether part-time work would fill a gap and whether your investments are set up to support those plans. A transition-to-retirement approach may suit some people, but it won't suit everyone, so weigh it against your own circumstances.

6. Could aged care become part of your family's future?

The holiday season is a natural time to notice how older relatives are getting on. Look for signs that everyday tasks are becoming harder, from managing stairs to keeping on top of bills. Then start a conversation about care needs and future wishes before a crisis forces the decision.

If aged care may be on the horizon, think through the financial side early. Consider how costs could draw on savings and other assets, whether the family home should be kept or sold, and how those choices affect other family members. Specialist aged care financial advice can help you map the options, though it's most useful when you ask for it before the pressure builds.

7. Would your family cope if something unexpected happened?

Insurance can feel like money spent for nothing, especially when premiums get paid year after year without a claim. That's exactly the point. Cover is there for the years you don't want to need it, and the moments you do need it are the ones where it matters most.

Think through the scenarios that would hurt most: an illness, an injury that stops you working, or the loss of a loved one. The right cover can replace lost income, meet essential living costs and ease pressure on the people who depend on you. Review what you hold now and ask whether it still reflects your job, your debts and your family. The aim isn't the biggest policy you can find. It's the right protection at a price your budget can sustain, and an insurance advisor can help you test that balance against your own numbers.

Where to start

You don't need to answer all seven questions in one sitting. Pick the one that worries you most, work through it, and let the rest follow. The people who tend to feel most in control of their money aren't the ones with perfect plans. They're the ones who check in regularly and adjust when life changes.

My read is that the highest-value question is usually the tax one, because it's the easiest to miss and the hardest to undo. Get that right, then look at super and concentration. Heading into 2027 with a clear picture of where you stand is a practical way to make the year ahead feel less like guesswork.