001 — Welcome to Sleepwalk Money

I've spent nearly three decades as a Financial Planner talking to people about money.

I've sat across the table from people building wealth, people worried they don't have enough, people who have accumulated considerable wealth, and people getting close to retirement.

There's something I've noticed over the years that I can't quite shake.

I'll sit across from someone who has worked for 40-plus years.

They've raised a family, bought a house, paid down a mortgage, contributed to super, saved, invested and generally done all the things we're told we should do if we want to be financially secure.

They've been responsible.

They've made sacrifices.

And now they're approaching retirement.

On paper, this should be the happy ending.

This is what all those years of hard work were supposed to produce.

After four decades of getting up, going to work, paying bills and putting money away, they finally get to stop.

They've reached the finish line.

This is apparently the point at which they're given permission to live life.

But sometimes, sitting there listening to them talk about retirement, I find myself thinking something I probably shouldn't say out loud:

I hope you get to enjoy it.

Because the person sitting in front of me isn't the same person who started that journey 40-plus years earlier.

They're older.

They're tired.

They're grey.

Some are outright depleted.

They don't necessarily have the same energy they once had.

Their parents may be gone. Their children have grown up and left home. Friends have moved away, are getting older themselves, or are dead.

Some of the things they dreamed about doing at 30 don't seem quite as important at 65.

And there's one thing they definitely have less of.

Time.

That's the part that bothers me most.

Most people are incredibly good at accumulating money.

We can put money into super, buy shares, buy property, pay down debt and watch a balance grow over decades.

But we can't accumulate time.

We can't put another ten years into an offset account.

We can't salary sacrifice another 5% of our youth into super.

Once those years are gone, they're gone.

And yet we spend an enormous amount of our younger lives accumulating financial assets for a future version of ourselves who may not be anything like the person we are today.

Maybe that future version of us will be healthy and energetic.

Maybe we'll still want to do all the things we've dreamed about doing.

Or perhaps we'll have completely different interests.

We might have the money but not the energy or health.

Maybe we don't even make the finish line.

We simply don't know.

Nobody knows.

And yet we behave as though the future is guaranteed.

Most of us are handed a script for how life is supposed to work.

Get an education.

Get a job.

Work hard.

Earn more.

Chase the promotion.

Buy a house.

Pay off the mortgage.

Save.

Invest.

Put money into super.

Eventually, somewhere around 65, you're given permission to stop.

Then you can enjoy yourself.

When you actually write it down like that, it's a remarkably strange arrangement.

We accept a 3% raise that might yield ~$20 a week after tax and call it progress. In the name of "progression", we climb the ladder to trade 20 additional hours of high-stakes stress for a minor salary bump, while paying a constant micro-toll of surcharges, fees, and convenience taxes just to survive the working week.

We spend some of the most energetic and physically capable decades of our lives working to accumulate enough money to enjoy the years when we're likely to have less energy and fewer years remaining.

It's as if the here and now doesn't really matter sometimes.

And then there's the time you actually spend at work.

If work didn't pay you, would you still show up each day?

Do you really enjoy being told when to come in, when you can have a lunch break, when you can leave and when you can take holidays?

Do you love performative meetings, corporate jargon, and being told you're a "valuable asset" right before being restructured?

I'm not anti-work.

I'm not anti-money.

I'm not anti-business.

I'm certainly not suggesting everyone should tell their manager to go fuck themselves and quit their job tomorrow.

What I am against is sleepwalking.

More specifically, I'm against the kind of financial sleepwalking that allows us to spend decades making enormous decisions about our money and our lives without ever stopping to ask why we're making them.

I'm against people putting off the things they're passionate about today, telling themselves they can do them when they eventually retire.

I'm against people trying to optimise every tiny financial decision while ignoring the enormous life decisions happening around them.

Saving $5 on a coffee is not going to determine whether you can retire.

Pick your battles.

We spend a large amount of time asking how much money we need.

How much should we have in super?

How much should we save?

How much is our house worth?

How much income will we need in retirement?

How much can we afford to spend?

These are all reasonable questions.

But I think there's another question we should ask much more often:

What is the money actually for?

Not theoretically.

Actually.

What are you sacrificing to accumulate it?

What does another $100,000 really give you?

What does another year of work provide?

What are you postponing while you're chasing the next financial milestone?

What are you saying no to?

And perhaps most importantly:

When is enough actually enough?

Because "enough" is a funny thing.

The goalposts keep moving.

You think $500,000 will be enough, and then it's a million.

Then it's two million.

Then three.

Then you need to pay off the mortgage, help the kids, upgrade the house, build a bigger buffer or accumulate just a little bit more.

The goalposts move, and often we barely notice.

That's what I mean by sleepwalking.

I don't mean stupidity, laziness or failure.

I mean moving through life following a familiar path without stopping often enough to ask:

What the hell are we actually doing?

Maybe we don't just have a cost-of-living crisis.

Maybe we have a cost-of-status crisis too.

Here's the first mistake.

We let other people become the yardstick for what success is supposed to look like.

Who made the Joneses next door the benchmark for success?

Their house might be nice.

Their car might be new.

But we still don't know whether they're living a successful life. Half the time, the neighbour with the European SUV and private school fees is drowning in debt, living pay-check to pay-check on $300,000 a year. We ruin our health and burn our prime years trying to match a lifestyle that is fundamentally illiquid and insecure.

We look at the visible evidence of someone's life and quietly turn it into evidence that they're doing better than we are.

Nothing about our life has changed.

Someone else's has.

Yet somehow we're the ones who feel "behind".

We're not necessarily trying to become rich.

We're trying not to feel behind.

That's an expensive way to live.

If you let other people define success, there is no point at which you arrive.

The goalposts just keep moving.

So perhaps the first question isn't:

"How much do I need to keep up?"

It's:

"Who decided I needed to keep up in the first place?"

You don't have to run someone else's race.

There are plenty of places where you can find someone telling you which ETF or shares to buy, which super fund you should invest in, or which postcodes are supposedly the next property boom.

There's value in that information.

I'm not suggesting otherwise.

But that's not really what I'm here for.

I'm more interested in questioning what money is, the pursuit of money, human behaviour around money, and whether life has just become a rinse-and-repeat cycle of turning up to work, paying bills, buying shit we don't need, saving a bit for an abstract future, then doing it all again until we've depleted ourselves.

These are the things I'm interested in.

And perhaps the biggest question of all is whether being financially successful and living a successful life are necessarily the same thing.

I'm not writing this because I've figured life out.

Quite the opposite.

The older I get, the more questions I seem to have.

I look at people and wonder whether we've become obsessed with both the accumulation and consumption of money.

We know how to make it.

We know how to spend it.

We know how to invest it.

But do we know how to use it?

Do we understand the real cost of obtaining it?

Do we know what enough actually means?

And perhaps most importantly, do we know what we're actually trying to buy with all those years of work?

That's what Sleepwalk Money is about. I’ll dive into areas such as the below and more:

• Deconstructing Corporate Energy Theft: The promotion traps, performance review farces, and phantom pay raises that burn your best years.

• Systemic Leaks & Micro-Tolls: How bracket creep, friction costs, and convenience spending quietly drain your freedom.

• Building the Equity Engine: Simple index funds, dividend cash flow, and shifting from a wage-earner to owning a piece of the pie.

• The Asymmetry of Ageing: Balancing health-span with wealth-span, and why $10,000 spent at age 28 yields memory dividends that age 68 cannot buy.

• Breaking the Cost-of-Status: Escaping the McMansion paradox, private school traps, and postcode penalties to define your own "Enough."

• Advisory Receipts & Practical Moves: Real observations from decades of client sessions, paired with practical levers to claim back your time and agency.

I'm not here to tell you how to live your life.

I'm not going to tell you to quit your job, save less, spend more or retire at 40.

I'd rather ask better questions.

What is enough?

What is this money actually for?

What are you buying with another year of work?

What are you postponing?

And if money is supposed to help us build a life, are we actually using it that way?

Are we being fooled into thinking we’re “getting ahead?”

Maybe you're doing everything right.

Maybe you're not.

Maybe there isn't a right answer.

But before you spend another year doing what you're doing, perhaps it's worth asking what you're doing it for.

Welcome to Sleepwalk Money.