How One Conversation Cost My Neighbour $1.5 Million (And What It Taught Me About Property Timing)

A few years back, I was chatting with my neighbour.

He owned an investment property on the Gold Coast, and he'd made a decision: it was time to sell.

"I'm getting out," he said. "Market feels uncertain. I want to lock in my profit."

Now, I'm not in the business of telling people what to do with their money. But I've been doing this for three decades, and I had a feeling about where things were heading.

So I shared my thoughts:

"Listen, this isn't advice — just my opinion — but I wouldn't sell right now. I think the market's about to turn. You might be leaving money on the table."

He thanked me. Nice guy. But he'd already made up his mind.

He sold it for just over a million dollars.

Two years later, that same property resold for $2.5 million.

That's $1.5 million he didn't get to see.

Now here's the thing...

He's not stupid. He's not reckless. He's actually a pretty sharp guy.

But like most of us, he was thinking emotionally and justifying it intellectually.

He felt like it was time to get out, so he found reasons to support that feeling.

And it cost him dearly.

Why Property Timing Matters More Than You Think

After three decades in property, I've noticed this pattern again and again:

The quality of the decision often matters more than the quality of the property.

You can own a great property and still end up disappointed if you buy or sell at the wrong time.

Let me show you what I mean.

There's a unit I've been watching. Here's its journey:

• 2007: Sold for $680,000

• 2020: Sold for $395,000

• 2025: Just resold for $825,000

Same property. Three different owners. Completely different experiences.

The person who bought in 2007 and sold in 2020? They lost $285,000 over 13 years.

The person who bought in 2020 and sold in 2025? They made $430,000 in just 5 years.

Same property. Different timing.

That's a $715,000 difference in outcome based largely on when you bought and when you sold.

And this is one reason why many investors never get past owning one property. One disappointing experience can be enough to put you off for good.

My Own Journey To Understanding This

I wasn't always smart about property investing.

When I was young, we never had much money. Sometimes my mom skipped meals to make sure I had food.

So for me, having money seemed like it would solve everything.

I thought "rich" meant having lots of money. Big portfolio. Impressive numbers.

I chased deals. I took risks. And yes, I made some money.

But I also made some costly mistakes that kept me awake at night. More than once, I let greed cloud my judgment.

Then one day, I sat down and looked at every property I'd ever bought.

What I paid. What they were worth. Which ones actually performed well.

And I noticed something interesting:

My best investments weren't the flashy ones or the "can't miss" opportunities everyone was excited about.

They were the steady, solid properties that were genuinely profitable, relatively low risk, and basically paid for themselves.

Without even realizing it, I'd become a contrarian investor.

Buying when people were hesitant. Selling when everyone else was buying.

And I learned what "rich" actually means to me:

Rich isn't having lots of money. Rich is having no debt plus enough money to do everything on your bucket list without stress.

That shift in perspective changed everything.

What I Notice Smart Buyers Doing Differently

Here's what I see happening in the market:

A lot of people buy investment properties the way they buy new cars.

They look at what's available, choose something that appeals to them, and someone helps them buy it.

But sometimes they don't realize that without looking carefully at what they're buying, it might not perform the way they hope.

The challenge? Many people are following the crowd.

They're jumping into properties without realizing the experienced investors have often already identified the growth areas before they become obvious to everyone else.

And if they're buying new off-the-plan properties? A significant chunk of the purchase price can be wrapped up in fees, commissions, and taxes before they even take ownership.

Smart buyers tend to think differently.

They don't make decisions based on feelings alone. They don't just follow headlines. And they take their time with big financial decisions.

They think in layers:

Layer One: Timing Matters

They understand that markets move in cycles. Buying a good property at the wrong point in the cycle can still lead to disappointment.

Remember that unit that lost $285,000 in value? That's a real example.

Layer Two: Understanding Risk First

They look at what could go wrong before getting excited about what could go right.

I've seen people get so focused on potential gains that they overlook warning signs.

Being cautious isn't pessimistic — it's smart.

Layer Three: Looking At The Bigger Picture

They pay attention to infrastructure projects, population trends, and policy changes — not just media stories or what people are saying at dinner parties.

Layer Four: Considering What You Might Miss

Here's an example from my own family:

Someone close to me wanted to buy in a particular suburb but kept saving for a bigger deposit.

I suggested: "You might not be able to save faster than the market grows. Consider buying something more affordable now and using that growth to help you get your dream property later."

They decided to keep waiting.

And they've watched prices rise by over $100,000 while they saved.

Smart buyers understand that buying something isn't always better than waiting for the right opportunity.

But waiting indefinitely isn't really a strategy either.

Two Different Approaches To Building Wealth Through Property

There are basically two ways you can approach this, and understanding the difference is helpful:

Approach One: The Long Game

Buy a solid property in a good area and let time work in your favor over 15 to 20 years.

You're asking: "Will this area still be desirable in 10 to 20 years?"

This is the "buy and hold" approach. It works well, though it takes patience.

Approach Two: The Active Strategy

Buy before an area has fully grown, add value where possible, then consider selling to reinvest the profits.

This uses market timing and cycles to build wealth more quickly.

You're asking: "Where are the opportunities right now?"

Here's an example from my own experience:

I bought a property for $300,000. We improved it strategically and sold it a few years later for $800,000.

That property is probably worth $1.1 million today, but we took our profit when the timing felt right and reinvested it elsewhere.

Another example: In 2021, I had some cash available and bought a unit for $138,000. It's currently valued at $250,000.

That's nice capital growth, but the rental income alone performs much better than leaving money in the bank.

These approaches require different strategies.

Many people don't realize this distinction, which can lead to confusion or disappointing results.

What This Has Meant For Our Lives

Today, I have a debt-free property portfolio that gives us the freedom to travel without financial worry.

We've been able to do things that seemed impossible when I was stressed about money:

• Travelled across Europe aboard the famous Orient Express

• Rode camels through the Sahara Desert

• Went on an African safari

• Saw Broadway shows

• Dined at some wonderful restaurants around the world

Not because we're "wealthy" in the flashy sense.

But because we have no debt and enough passive income to live the life we want.

That's what this is really about for us.

Not impressing anyone. Not having the biggest portfolio.

Freedom. Choice. Peace of mind.

Some Things That Consistently Work

Here's what tends to work well, regardless of which approach you choose:

Buy a good property in a good area.

Add value where it makes sense.

But knowing which strategy fits your situation and when to apply it? That's where experience helps.

And right now, in this phase of the market cycle, there are some interesting opportunities emerging.

But positioning yourself to take advantage of them takes some planning.

Learning From Experience (So You Don't Have To Make The Same Mistakes)

Look, I understand this can feel like a lot to take in.

Thirty years of lessons condensed into one article.

That's why I've organized everything into a simple seven-step process you can follow at your own pace.

This roadmap walks you through:

• How to move forward based on YOUR specific situation

• How to recognize good opportunities before they become obvious

• And importantly, how to avoid some common pitfalls

I'm offering this as a free download because I genuinely don't like seeing good people get disappointing results from well-intentioned decisions.

This is the same process we use with our private clients.

The same approach that's helped us build a life we love, completely debt-free with the freedom to make choices based on what we want, not what we can afford.

It's taken me 30 years of learning — both from successes and mistakes — to develop this.

If you'd like the complete seven-step roadmap, you can download it free when you subscribe to the Better Call Shane newsletter.

Because here's the thing:

My neighbour can't go back and change his decision.

The person who sold in 2020 can't undo that outcome.

My family member can't reclaim those years of waiting.

But you? You're reading this right now, which means you're thinking about this stuff.

And that puts you ahead of most people.

Take your time. Think it through. And when you're ready, I'm here to help.