The One Question Most Investors Avoid – That Turns Fear Into Action
The Moment I Nearly Walked Away
There’s a moment in every investor’s journey where fear whispers louder than logic.
For me, it came on a deal years ago that should’ve been straightforward – a small subdivision that ticked all the right boxes.
– The numbers stacked.
– The builder was lined up.
– The council pre-lodgement went smoothly.
Still, I sat there late one night staring at the spreadsheet, second-guessing everything.
– What if the neighbour objected?
– What if construction costs blew out?
– What if I just wasn’t ready for the jump?
It wasn’t the deal that was the problem, it was my mindset.
Fear Isn’t the Enemy
Most people think fear means stop.
But fear’s job isn’t to paralyse you, it’s to protect you. It’s a signal that something matters.
In property, that signal can easily get misread.
We start treating ordinary risk like danger, even though the two aren’t the same thing.
The key isn’t to eliminate fear. It’s to learn from it without letting it run the show.
The One Question That Changed Everything
That night, after too much coffee and not enough clarity, I asked myself a question that’s stayed with me ever since:
“What if it turns out better than I expect?”
Simple, but powerful.
Because here’s what usually happens… We imagine every possible way something could go wrong, yet rarely stop to picture how it could go right.
That question flipped the whole situation.
It forced me to zoom out, see how many times things had actually worked out, and recognise that even the tough moments had taught me something valuable.
The deal went ahead.
It wasn’t perfect – they never are – but it became one of the turning points in my journey.
Why This Works
You’ve probably heard me say it before: 95% of the time, the fear doesn’t become reality.
We’re far more resilient than we give ourselves credit for.
Think back to a time you thought everything was falling apart… Maybe a builder disappeared, a DA stalled, or a lender changed terms mid-deal.
It felt huge in the moment, but you handled it.
You found a workaround, a new contact, or a better approach.
You’re still here.
That’s the proof.
Fear doesn’t mean stop, it means prepare.
There’s No Wrong Path, Only No Path
When I mentor investors who feel stuck, I often remind them:
There’s rarely a “right” or “wrong” decision, only action or inaction.
Making a move – even a small one – gives you feedback.
Standing still gives you nothing.
When you move, you learn.
When you wait, you just worry.
The market doesn’t reward perfection, it rewards momentum.
How to Reframe Fear in Practice
Here’s the 3-step framework I use with mentoring clients when fear starts creeping in:
1. Name it.
Write down the exact fear, not the vague feeling.
“I’m scared this project will go over budget.”
2. Flip it.
Ask: “What if it turns out better than I expect?”
Then list three reasons that could be true.
3. Plan one action.
Take a small, specific step that keeps you moving – call the builder, check recent sales, update the feaso.
Momentum doesn’t come from confidence.
Confidence comes from momentum.
When Things Go “Wrong”
If you’ve been around property long enough, you already know that “wrong” often turns into “right” later.
Deals that fall over make space for better ones.
Delays often lead to more profit as markets catch up.
Mistakes force you to build better systems.
Looking back, some of my best lessons came disguised as problems.
They forced me to grow, and that growth made the next deal easier.
So next time something unravels, pause before calling it bad luck.
It might just be a re-direction.
The Hidden Cost of Inaction
People think acting too soon is risky.
In truth, waiting too long is what costs the most.
While you’re standing on the sidelines double-checking every variable, someone else is making offers, building equity, learning through experience.
The difference between a fearful investor and a confident one isn’t knowledge, it’s action.
How to Build a Fear-Resistant Routine
Here’s how to make progress even when fear’s in the room:
- Limit your information window. Spend 48 hours assessing a deal, then decide — yes, no, or park it. If that sounds familiar, read my 48-Hour Rule blog.
- Track wins weekly. Write down every time you faced uncertainty and took action anyway. Momentum compounds when you measure it.
- Revisit your “why.” Fear fades when purpose grows. Keep your bigger goal in sight – financial freedom, family time, legacy, whatever drives you.
Related Reading
If this topic resonates, you might like two earlier pieces that dig deeper into overcoming fear and performance mindset:
- 9 Magic Words Used by World Champions to Transform the Mind, Erase All Fears, and Get In the Zone
- What I Do When I’m Afraid
Both expand on the same truth that fear isn’t something to fix, it’s something to work with.
Final Reflection
Fear will never disappear from investing.
It’s part of every growth phase, every decision, every leap forward.
But you get to decide whether it’s a barrier or a compass.
Next time doubt starts whispering, ask yourself the one question that turns fear into action:
“What if it turns out better than I expect?”
Then take one small step forward because action, not certainty, is what builds confidence.
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