Does Property Investing Really Make You Financially Free?

It’s what I call the freedom illusion.

Having invested in property for over 30 years, and spent the last 22 years helping people just like you become more successful property investors, I can tell you this: yes, for some people, property absolutely does set them free.

But for a surprisingly large number of investors… it doesn’t.

That’s the trap I want to help you avoid.

The Income Replacement Myth

Many people start out in property with the goal of replacing their job income. Maybe they enjoy what they do, maybe they don’t. Either way, the idea of generating income through property — ideally passive income — sounds like the dream.

The problem is, people often misunderstand what “passive” really means. They think it means no work. And that’s just not true.

Yes, property can become passive over time, but you’ve got to put in the effort upfront. You’ve got to find the deals, secure the finance, refurb the property (if needed), and get it set up for rental. Only then can you hand over the reins to a letting agent or property manager.

And that’s where the next trap lies.

The Landlord Trap

When I first started out, I fell right into what I call the landlord trap. I managed my own properties because I didn’t want to pay someone else to do it. That fee felt like it was eating into my income.

At first, it was fine. Managing a couple of properties on the side is doable. But as the portfolio grows, so does the time you spend managing it. And eventually, you’ve swapped one job for another — except now you’re a property manager.

And if I’m being honest, managing properties just isn’t fun. It’s an important job, sure. The tenants and properties need looking after. But that doesn’t mean you need to be the one doing it.

The key mindset shift is this: stop focusing on the cost of paying a management agent, and start focusing on the value of your time. Freeing up your time allows you to buy more properties — or, better yet, do more of what you want to do.

Real Freedom Comes From Choice

People sometimes ask me, “Simon, if you’re financially independent, why are you still teaching people about property?”

And when I hear that, I know the person asking is probably still stuck in the time-for-money mindset.

When you’re truly financially free — when income keeps coming in whether you work or not — you’ve got choice. You can choose what to do with your time. And for me, I choose to teach, because I enjoy it. I love helping people. I love hearing the stories of how property has changed their lives.

I might’ve been a catalyst for them — helping them believe in themselves, giving them strategies, holding them accountable — but they did the work. And now they’re reaping the rewards.

That’s what I love about property. You do the work once, and you can get paid forever.

My Journey to Freedom


When I left my job at Cadbury’s in 2001 — which, by the way, was my dream job — I hadn’t quite replaced my full income. But I had enough rental income to cover my living expenses, and I knew property worked.

So instead of going to work each day, I invested that time into building my portfolio. Within two years, I’d fully replaced my income. More importantly, I had other people managing the properties for me. And that’s when I launched the Property Investors Network, back in 2003.

For the past 22 years, I’ve been helping people do the same. And because I love what I do, it doesn’t feel like work.

If you can get paid to do something you love — well, that’s the dream, isn’t it?

Why Are You Investing in Property?

That’s the question I want to leave with you today. Why are you doing this?

Some people love property for its own sake — they enjoy taking old buildings, renovating them, and bringing them back to life. If that’s you, fantastic.

But for most people, I suspect that’s not the case. Most people have other things they want to do with their lives. Property is just the vehicle.

So get really clear on what you want property to give you. First, replace your income. Then, replace your time — which means not spending all your time managing the properties.

And while property may never be 100% passive (I still spend about an hour a week managing my agents via Zoom), it can be very low maintenance. Just remember: you can delegate, but you can’t abdicate responsibility. Ultimately, as the landlord, you’re still accountable.

Build a Team, Not a Job

Finding the right letting agents, builders, mortgage brokers — your whole power team — makes a huge difference. The best way to find them? Word of mouth. Speak to other investors. Head to your local pin meeting and ask around.

The right team will free up your time and help you build a sustainable portfolio, not just a busy one.

And please, don’t fall into the trap of endlessly acquiring properties without stopping to enjoy the results. I’ve met countless investors who are asset-rich but cash-poor, because they keep ploughing everything back into the next deal.

At some point, you’ve got to say, this is enough.

It’s Not About the Property — It’s About the Life

Sometimes, people don’t know what they want to do with their freedom — so they just keep doing property. But take a step back. Give yourself space. Travel. Reflect. Work out what you really want from life.

Because if you do something you love, and it adds value to others, that’s where real success and fulfilment lies.

Property investing isn’t the destination — it’s the vehicle. It can give you the financial and time freedom to build the life you truly want.

Just make sure you don’t spend all your time doing property and forget to live the life you were building it for in the first place.

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