A phone ringing on a desk symbolising pressure and responsibility in property investing

The Question Every Property Investor Avoids Asking

January 12, 20263 min read

Do you have what it takes to be a property investor in South Africa

Introduction

There’s a moment most people never talk about. It happens just before the phone rings.

Your heart doesn’t race — it gets heavier. Your chest tightens. Not panic yet, just pressure. Your mind fills in the blanks before reality even arrives. This isn’t going to be good.

You’re doing something ordinary. Coffee halfway to your mouth. Emails open. The day still pretending to be normal. And then the phone rings.

In that moment, before you answer, something becomes very clear. This isn’t about property anymore. It’s about whether you’re built to carry responsibility when things don’t go your way.

Most People Want the Outcome, Not the Work

When most people say they want to be property investors, what they usually mean is that they want the outcome.

They want the Airbnb cash flow.
They want the clever structure.
They want the story of making R10,000 a month “passively.”

There’s nothing wrong with wanting outcomes. But outcomes are not the work.

When I started, I thought property investing was about being smart. I’d read the books. I knew the language. I could talk numbers and structures. I thought that meant I was trained to be an investor.

What I didn’t realize was that I wasn’t becoming an investor. I was becoming a business owner.

No one prepares you for that shift — and that’s why so many so-called “safe investors” struggle the most.

Why Property Is Never Just Passive

On paper, many property strategies look elegant.

Installment sales look clean. You take over a bond, structure the deal, avoid new finance. But in real life, you carry the risk in your nervous system. You’re responsible even when the seller technically still owns the property. You manage expectations, time, and fear — yours and everyone else’s.

Rent-to-rent and Airbnb promise passive income until a guest trashes the place, the landlord panics, occupancy drops, or a cleaner doesn’t pitch up. Suddenly, you’re not an investor. You’re operations. Customer service. Problem-solving. Everything.

Even flips work this way. I’ve made R500,000 on a flip in 24 hours — and I’ve also carried months of uncertainty, cash flow pressure, legal delays, and other people’s emotions to get there.

The money comes after the responsibility, not before it.

Fault Versus Responsibility

There’s a distinction that changes everything.

Things may not be your fault — but they are always your responsibility.

It’s not your fault if a tenant loses their job.
It’s not your fault if interest rates rise.
It’s not your fault if a deal falls apart.

But if you can’t carry that responsibility without resentment or blame, property will break you.

Property doesn’t reward optimism. It rewards maturity.

The Question Most People Never Ask

Before chasing another deal, there are a few uncomfortable questions worth answering honestly.

Can you do the unsexy work without praise — the work no one sees?

Can you sit with pressure without outsourcing blame?

Can you delay gratification longer than feels fair?

If you need constant wins to stay motivated, property will exhaust you before it rewards you.

This is why “safe investors” often struggle the most. Safety tends to avoid responsibility — and avoidance kills momentum faster than risk ever will.

Conclusion

Property doesn’t make you someone new. It reveals who you already were under pressure.

The real question isn’t whether you can make money.

It’s whether you’re willing to carry the responsibility that comes with it.

WATCH / LISTEN

Watch or Listen

If you’d prefer to watch this episode on YouTube, you can find the full podcast here:
https://www.youtube.com/@MeetMichaelBowen/podcasts

Or, if you’d rather listen on Apple Podcasts, Spotify, amazon or your other favorite PodCast platform, you can find the episode here:

https://flipthescriptmmb.podbean.com/

To explore more thinking on property, freedom, and designing life intentionally, visit:
https://meetmichaelbowen.com/start-here

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