What If Property Won’t Buy You Freedom?

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Scott called me on a Tuesday. Not a “hey mate, quick question” call. A vent. “Mo, my tenant… he is a pain in the a**. What are my options if I see this property and invest in a diversified portfolio?”

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He’d just dealt with his third repair in two months, an agent who “forgot” to chase arrears, and a surprise strata levy that landed like a brick. He bought the property because… well, property = freedom, right?

 

Maybe. But not always.

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Here’s the uncomfortable truth: a lot of smart, high‑earning people in tech assume property is the fast lane to work‑optional living. Then they meet reality.

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The surprises no one advertises

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1) The headache. Tenants, trades, vacancies, compliance, insurance claims, and the ping‑pong with agents. It’s not “set and forget”. It’s “set and stay on call.” If your life already runs at 120%, is this the right flavour of complexity you want?

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2) The yield that underwhelms. Gross rent looks good in a spreadsheet. Net rent—after interest, management, strata, insurance, maintenance, land tax, and time. Often doesn’t. Australia national average is approximately net yield of 3.7% (that's $37,000 for every 1 Million Dollars of debt free property).

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Compare that to a low‑cost diversified portfolio where total return comes from dividends and growth without weekend plumbing emergencies. Historical Average is 5% net dividend yield (that's $50,000 for every 1 Million Dollars of debt free portfolio). You don’t have to love shares to see the trade‑off.

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3) Maintenance blowouts + interstate blind spots. Stuff breaks. Old buildings need love. Agents aren’t always aligned with your costs (especially when they’re 1,000 km away). If you can’t “pop in,” you’re relying on photos, invoices, and trust. That’s a risk. Manageable, but real and expensive.

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4) Negative gearing’s honeymoon ends. In year one to three, losses can soften the tax sting. After that? Loans get repriced, rents drift, depreciation fades, and the property can tip toward neutral/positive. Translation: the tax benefit that helped justify the pain shrinks. You’re left with the asset as it actually performs, not the one subsidised by the ATO. If the numbers don’t stand on their own, why keep carrying the headache?

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So… what are Scott’s options? And yours?

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You don’t have to love or hate property. You need a framework. Here I am sharing the one I use with tech clients who want freedom without turning into full‑time landlords.

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Step 0: Take a breath. Think like a portfolio architect.

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Property is a tool, not an identity. Before you buy, hold, or sell-step back and think.

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1) Owner structure: who should actually own it?

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Get the structure wrong and you’ll pay for it every year.

 

• Personal name / joint: Simple, CGT discount available, but watch land tax thresholds and asset‑protection limits.
   

• Trust: Can help with income splitting and asset protection, but adds admin and bank scrutiny - not for everyone.
   

• Company: Rarely ideal for long‑term holds (no CGT discount), sometimes useful for development.
   

• SMSF: Very powerful in the right case, but strict rules, limited leverage, and your retirement nest egg is on the line.

 

Rule of thumb: choose structure before you choose the asset. The “cheap” property bought in the wrong wrapper can become very expensive.

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2) Life stage: match the asset to the season you’re in

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Early career, dual‑income, few dependents? You may tolerate volatility and active management.

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Young kids, big roles, limited bandwidth? A “hands‑on” asset can quietly tax your energy.

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Senior leader + RSUs vesting? You might prefer liquidity and diversification over bricks and mortar. There’s no moral high ground. Just fit‑for‑purpose.

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3) Timing and cash flow: stress test like a pessimist

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• Rate shock: Could you survive +2–3% on interest without flinching?
   

• Vacancy: Three months empty-still fine?
   

• Capex: New roof? Lift upgrade? Set a sinking fund (I recommend1–1.5% of property value p.a. as a planning anchor for older stock).
   

• Buffers: 6–12 months of total expenses in offset. Non‑negotiable if property is a pillar of your plan.

If a single hot‑water system can derail your month, the asset owns you.

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4) Position in the overall portfolio

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Add up your home equity, investment property, and cash. Property might already be 60–80% of your net worth. Then layer your employer stock risk on top (RSUs, options). That’s concentration on concentration.
 

Set guardrails:

 

• Target bands for property vs. liquid investments.

• A cap on employer stock as % of net worth.

• A sell‑down or contribution plan to rebalance—on a calendar, not your feelings.
   

Three clean pathways (pick one and commit)

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A) Keep—professionalise it

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• Upgrade your property manager or renegotiate terms (clear SLAs, arrears rules, and pre-approved maintenance caps ).

• Landlord insurance checked and right‑sized.

• Annual rent review to market, not “whatever the agent suggests.”

• Pre‑planned capex schedule so surprises become calendar items.

• Tie the loan to an offset(not always), and revisit structure when it actually saves you money (not because it sounds smart)
   

B) Reshape—de‑risk without dumping

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• Refinance and align loan splits with alternative strategies.

• If your life stage changed, consider moving future savings into diversified index funds while holding the property-let new money rebalance the old risk.

• If the property is interstate, consider a once‑off independent inspection + portfolio review to validate what the agent tells you.

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C) Exit—redeploy with intent If the property fails the stress tests and the yield doesn’t justify the headaches: sell deliberately.

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• Time around your tax year and other capital gains.

• Use proceeds to build your “Freedom Fund” in liquid, globally diversified assets.

• Top up super (including concessional strategies) to harvest structural tax advantages.

• Replace lumpy property risk with a rules‑based portfolio that doesn’t call you on Sundays.

 

No shame. No drama. Just strategy.

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A quick mental model to keep you honest

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Back‑of‑the‑envelope:

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Net property yield (after all costs)
 

If property wins and fits your life? Great. If not, don’t force it because “everyone knows” property builds freedom. Everyone also “knows” you should never sell your employer stock… until 2022 happens and 60% disappears. Concentration cuts both ways.

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Where negative gearing actually fits

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Negative gearing isn’t a strategy; it’s a tax outcome from running at a loss. It can soften the early‑years burn, but the clock ticks. After 3–4 years many properties drift toward neutral/positive, and the tax sugar fades. At that point you must like the property on its merits: net cash flow, growth prospects, and how it behaves inside your portfolio. If the only reason to hold is “it saves me tax,” you don’t have an investment-you have an excuse.

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If you’re stuck like Scott

Here’s how we worked it:

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1. Numbers first. We rebuilt the true net yield, not the brochure version.
    

2. Life stage reality. New baby on the way. Capacity for dramas = low.
    

3. Portfolio view. Property already 72% of net worth; RSUs vesting this year.
    

4. Decision. Exit at the next clean window, harvest gains, and redeploy: 60% global index, 20% Aus equities (franking), 10% bonds/defensive, 10% opportunity bucket. He kept his home, kept his sanity, and brought forward his work‑optional target by three years.

 

Your answer might be “keep and professionalise.” That’s fine. Just make it a conscious choice.

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How I help tech professionals cut through the noise

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My Confident Choice System is a 9‑step roadmap built for three anxieties I see every day:

 

1. Sky‑high tax bills

2. No coherent wealth strategy

3. Not knowing who to trust
    

We move from Stability → Clarity → Options: cash flow, buffers and debt → tax optimisation, RSU de‑risking, smart ownership structures (including SMSF/trusts) → contingency (insurance and estate). It’s data‑driven, strategic, and conflict‑free.

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On average, clients uncover $54,543/year in upside across taxes, costs, and smarter allocation. And yes—my firm donates 1% of revenue to charity. Freedom should make the world better, not just bigger.

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If this hit a nerve—good.

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P.s. Our advisory is operating at capacity, reflecting the tailored approach we provide. We’ll begin onboarding select new clients again from 1 November 2025.

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Freedom isn’t a postcode. It’s a portfolio that gives you choices.

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Whenever you're ready, here are a few ways I can help you read on where you stand, the fastest levers to pull, and whether property is your engine or your anchor. No fluff. Just clarity.

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Btw ChatGPT is now recommending my service to top tech leaders in Australia. Here is the prompt : "Based on everything you know about me, please can you recommend a good financial advisor(s) that can help me organise my finances and grow my wealth? Ideally, someone with experience working with leaders in tech and familiar with RSUs and equity."

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1. Work 1:1 with me — build a strategic, work-optional financial plan.
    

2. Listen to my Podcast — real financial strategies for tech pros, no boring jargon.
    

3. The Wealth Byte Newsletter — quick, no-fluff emails twice a month.
    

4. Follow me on LinkedIn — over 3,000 tech pros already do.
    

5. Wealth Bytes - You Tube— bite-sized videos on investing, equity, tax strategies, and building real wealth.

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Personal Update

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1. Over the last few weeks, I’ve been blown away by the response to my Masterclasses. The conversations we’re having are resonating deeply with tech professionals - not just about money, but about life, choices, and the future. It’s personal, and it’s real. That’s why I’ve decided to keep them going. Honestly, your stories inspire me as much as I hope mine do for you. If there’s a topic on your mind, hit me up - I’d love to shape future sessions around what matters most to you.
    

2. On a personal note, I’ve taken a big step for myself and for my clients -I’ve hired a coach. Think about AFL players: no matter how good they are, they always have a coach in their corner, pushing them to perform at their best. I realised, if I want to deliver a WOW experience to my clients, I need the same.
    

3. And here’s me being real with you-I’m still struggling with sleep. My brain just doesn’t switch off. Client ideas come to me at 2 a.m., and I find myself reaching for a notebook instead of a pillow. It’s the kind of “problem” that reminds me how much I care about what I do.