Are You Undervaluing the Case for Upsizing Your Home?

A Story That Stuck With Me

As I think back over the years, there’s one story that stuck with me — one that perfectly captures how easily inaction can build up without anyone noticing.

A few years ago, I met a couple — let’s call them Peter and Elaine. Peter was 72, Elaine 67. They’d retired at different times, and like many couples, Peter had always taken the lead on financial decisions. They had over $1 million in financial assets outside their home — super, shares, a family trust. They were careful, conservative, and proud of what they’d built.

But they hadn’t moved their super into pension phase. They hadn’t reviewed their estate plan since their kids were teenagers. And they hadn’t really talked — not deeply — about what they wanted the next ten years to look like.

What struck me most was how much they’d missed by not planning together. Because of their age gap and separate financial strategies, they’d unknowingly left more than five years of Social Security entitlements on the table. And that moment was when the real purpose of retirement planning became clear for them — it wasn’t just about structures and tax; it was about reclaiming confidence and connection in this phase of life.

To help them move forward, we talked through what was possible. From there, we didn’t overhaul everything. Just a few key shifts that made all the difference:

• Transitioning their super saved them thousands in tax each year.
• Coordinating their income streams gave them access to benefits they didn’t know they qualified for.
• Updating their estate plan meant their kids wouldn’t inherit a tax headache if something happened unexpectedly.

But the biggest change? They started talking. Not just about money — about travel, family, legacy. About what mattered now. And that’s when Elaine said something I’ll never forget: “I didn’t realise how much we were leaving on the table. I thought doing nothing was safe — turns out, it was expensive.”

Who this applies to

This conversation is not universal. It’s most relevant for people who:

• aren’t currently living in their ideal long-term home
• are weighing up a first purchase and could potentially go a little higher
• or are thinking about upsizing, but haven’t properly tested the idea

This is not about buying the most expensive home possible. It’s about stepping back and asking a simple question – Have you actually tested whether the home you want is more within reach than you think?

For many people, the answer is no. They’ve either ruled it out too quickly or never analysed it in a structured way.

This is also something I’ve been thinking about personally. My wife Sallie and I bought our home back in 2015, before we had kids. It’s a home we still genuinely like. But if we’re being honest, in a perfect world we’d live a little closer to the beach and have a bit more space — particularly for living and entertaining.

Looking back, we could have afforded something closer to that “ideal” home at the time. We just never properly tested it. The gap between what we have and what we’d want today has grown significantly over the past decade as house prices have moved.

That doesn’t mean we’ve made a bad decision. But it does highlight something important — sometimes the real missed opportunity isn’t buying the wrong home, it’s not properly testing the right one when you had the chance.

It’s part of the reason I’m now approaching the idea of upsizing very differently. This time, the goal isn’t to make the perfect decision — it’s simply to make sure it’s a properly tested one.

What “testing it properly” really means

Testing the case for upsizing isn’t about seeing how much the bank will lend. It’s about understanding what it means for your broader plan.

That includes:

• your ongoing cash flow
• your ability to maintain buffers
• how resilient your position is to shocks
• and the impact on your other goals over time

A better home should not come at the expense of cash flow resilience or the ability to maintain adequate buffers. If it does, the strategy likely breaks down.

But what many people find is that once they properly work through the numbers, there can be more room than they initially assumed — particularly when decisions are based on long-term living rather than short-term thinking.

That is very different from recklessly stretching. It’s about being deliberate and measured. For most people, this is also where things tend to stop. They rely on a borrowing estimate or a rough rule of thumb — neither of which really answers the question.

Properly testing it means mapping the decision against your life over time. What does it look like not just this year, but over the next 5, 10 and 20 years? How does it affect your ability to save, invest, take time off, or absorb unexpected events?

That level of clarity usually requires more than instinct. It requires stepping back and laying out your goals alongside your financial position — properly. I’ve written about this concept previously as lifetime goal mapping. It’s not about getting the answer perfect, but about making sure the decision is tested in the context of the life you actually want to live.

The part we don’t talk about enough

There’s also something else that often gets overlooked.

For most Australians, a home carries a lot of emotional weight. It’s where life actually happens — where families are raised, routines are built, and memories are made over long periods of time. The sense of comfort, stability and connection to a community isn’t easily captured in a spreadsheet.

Without overstating it, improving your lifestyle — and how your family experiences day-to-day life — can, in some cases, matter more than marginal differences in long-term investment returns. For some households, that trade-off is not only acceptable — it’s entirely rational.

Why timing can matter more than you think

When people talk about property, the focus is often on whether prices are “expensive” or “cheap”. For someone upgrading a home, that’s not always the most useful lens. What matters more is the gap between where you are now and where you want to be.

In markets where growth has been more subdued at times, there can be periods where that gap becomes more manageable. Even in more expensive markets, different segments don’t always move in sync.

When conditions are flatter, the question shifts from “Is now a good time to buy?” to “Is the step-up into the home we actually want more achievable than it used to be?”

For the right household, that’s a far more useful question.

Keeping optionality, not relying on it

One concern people often raise is what happens later. What if income changes? What if you need access to capital?

These are valid questions. But they don’t automatically invalidate the decision — they simply create optionality. Some households may choose to downsize later. Others won’t. The point is not to rely on that outcome, but to recognise that it exists.

Living in a better long-term home is not, by default, a poor financial decision simply because it may be adjusted in the future.

The real question

In a financial world full of noise and competing ideas, there is value in stepping back and testing the obvious. Run the numbers on the upgrade gap. Understand the impact on your cash flow, your buffers and your broader plan. Map it out properly over time, rather than relying on a point-in-time estimate.  Have the conversation properly.

Because for some households, the missed opportunity isn’t failing to find the perfect investment. It’s failing to properly consider the home they actually wanted to live in.

Will you regret not properly testing the case for a better home while it was still within reach?