Jack’s Story

From Complexity to Clarity

Jack came to me with what looked like a straightforward question:

“Should I buy another property?”

On paper, he was in a strong position. A senior IT executive earning around $400,000 a year, with two investment properties, some shares, and cash on hand. But like so many people I meet, the numbers only told part of the story. 

Behind the spreadsheets was a life layered with complexity:

-          He lived in his parents’ home, paying them rent while also caring for them.

-          His relationship with his sibling was strained, which left him quietly anxious about what would happen when his parents passed away.

o   Would he lose the home he lived in?

o   Could he buy it out?

He was also eight years post-divorce, co-parenting one child and (still) supporting the other who had already left home. He had rebuilt his financial position – and should have been proud of the progress he’d made - but despite this, he carried a nagging sense that he should have been further ahead.

Looking around at the people he knew, he couldn’t get past the feeling that he’d never caught back up. Now, retirement wasn’t far away, and he was starting to doubt if he could keep doing it all himself.

The ‘Real’ Questions

When we first sat down, Jack told me he wanted to buy more property. But as we dug deeper, it became clear the question wasn’t really about property at all – it was about security.

He wanted to support his kids, travel with his partner, and maintain his lifestyle — but without the constant weight of feeling overextended.

Which meant that, deep down, below the enquiry about property, he was really worried about debt. Which felt odd to him, until he realise that despite his income, the idea of taking on more borrowing made him uneasy.

He’d worked so hard to get away from being in debt, to get out from under that heavy rock. Going back into debt felt necessary, but unappealing.  

So instead of simply “Can I buy another property?”, the real questions became:

• How can I retire without the burden of debt?

• How do I balance helping my family with preparing for the future?

• What’s the simplest way to build wealth from here?

• What should I do next?

The Lightbulb

Jack knew the basics of superannuation — he’d always made deductible contributions — but he had no idea he could add more through non-concessional contributions. Superannuation is such a multi-faceted thing that it can be hard for people to see all the angles, all the time.

Once he saw the numbers, the lightbulb moment was clear - here was a way to build his retirement balance steadily, in a low-tax environment, without taking on more loans. 

There was other ‘housekeeping’ work to be done as well:

-          We also restructured his insurances and mapped out different lifestyle and retirement scenarios.

-          We ran our eye over his existing superannuation make sure it remained suitable.

Step by step, we replaced ‘worry’ with ‘clarity’.

Keep It Simple, Champion

After modelling out Jack’s current financial trajectory, we were able to develop a clear, actionable plan for him.

The plan we arrived at was simple:

• Contribute regularly to super, topping up with additional non-concessional contributions when comfortable.

• Keep a good, comforting level of cash in his offset account.

• Adjust insurance cover to match his current needs.

That was it.

No complicated debt strategies.

No unnecessary risk.

Just a clear path to retirement — and the freedom to enjoy life along the way.

Hindsight

At the end of the process, Jack said something I hear often:

“I wish I’d done this sooner.”

It’s a reminder that even when life looks “fine” on the surface, the real value of advice lies in uncovering what’s underneath — the fears, the hidden questions, and the desire for simplicity.

Using this as the rock solid foundation for our advice means that every single piece of advice we provide is tailored to people’s unique, individual, complicated, wonderful, worrying and, at times, scary circumstances.

If you’d like to find out more about how our approach to advice could help you, or your clients, click on the link below to send us an email. We love chatting about this stuff!