You’re going to retire one day. Don’t be stupid enough to do it broke

It was a crisp, sunny day in Bathurst, NSW, in 2023.

My dad was at the local pub, celebrating the culmination of a business deal. He had also just turned 65 - the age many hail as the finish line of the rat race today.

I called him from Waterton Lakes, Alberta, where I was on a road trip, to congratulate him on both the deal and the birthday. But I also wanted to ask a bigger question: how did it feel to hit retirement age, and what lessons had he learned?

His answer has stayed with me ever since.

“Son, retirement will sneak up on you faster than you expect, and if you’re not prepared, you’re screwed.”

It’s one of the best personal finance lessons he ever gave me, and made me double-down on strategies like increasing super contributions and it certainly jolted my curiosity about optimising tax.

The retirement mistakes I’ve seen up close

More importantly, he gave me a front-row seat to what happens when people ignore it.

Through his circle of friends, colleagues and peers, I’ve seen what retirement looks like when people drift into it without a plan - and it’s rarely pretty.

Here are a few I want you to pay close attention to... because it shows how underestimating retirement planning can cause your quality of life to become completely unrecognisable, and at the worst possible time.

1) I’ve seen people make the baffling decision to quit work the moment they can access their super or the Age Pension. One family friend did exactly this, only to realise after his farewell lunch he still has a crippling mortgage to deal with and can't afford the lavish lifestyle he dreamed of.

Additionally, a costly divorce kicked him in the teeth; the matrimonial home sold at a loss, but due to the cost of living crisis, he and his ex-wife are still forced to live together, pay rent that the Age Pension barely covers, and say they may never be able to afford going overseas again.

2) I’ve seen others do what feels “safe” - withdraw all their super and make term deposits their entire asset allocation outside super (the ATO loved them for this). But by the time they hit their 70s, inflation and taxes had ravaged their capital, and the weekly lunch at their favourite Spanish restaurant became a once-in-a-blue-moon luxury.

3) Then there’s the widow who spent freely all her life, comforted by the belief that “the government will look after me.” They won't. Little did she realise the true cost of assisted living, where every service carries a price tag - from an insulin injection to help getting from the dining room back to her living quarters. Her daughter keeps bailing her out at great cost.

4) I’ve seen parents, acting from nothing but love, hand over a $400,000 house deposit from their super to help their newly married son and his wife into the property market - only to later realise they never properly protected that money from relationship breakdown risk.

The marriage fails, the daughter-in-law walks away with half the deposit and equity, and what was meant to be a family head start becomes a devastating retirement setback.

5) And I’ve also seen Australians, like many Livewire readers, do almost everything right: work hard, contribute diligently, invest consistently and try to stay ahead. Yet as the years rolled on, the rules kept shifting beneath them. Contribution caps changed, pension settings moved, and new taxes emerged. Not to mention, the cost of living has exploded. The finish line keeps moving just as they thought they were finally getting close.

And they are far from alone.

Why so many Australians feel uncertain

For those of you focused on retirement but feeling like you don’t quite have the pieces together, that’s normal.

As Felipe Araujo, CEO of Generation Life, puts it: “A secure, comfortable retirement is the ambition of every Australian - it’s their highest financial priority. But the journey feels less certain.”

New research from Generation Life’s 2025/26 Navigating Uncertainty Report shows retirement confidence among affluent Australians has deteriorated sharply since 2022, with:

• 69% now less confident about retiring comfortably
• 71% less confident about their financial security, and 
• 66% saying the super rules change too often and are too hard to follow.

What stands out is that retirement is still the top financial goal. The ambition hasn’t changed. But the path to achieving it feels far less certain, particularly as tax debates, superannuation rule changes and estate-planning complexity increasingly collide.

In fact, even the wealthiest Australians are worried. While 84% of high-net-worth Australians still believe Australia has one of the best retirement systems in the world, 61% are no longer confident it will adequately build and protect long-term savings.

It might sound like something out of la-la land, but I’ve had CEOs of funds management companies admit to me that, between expensive home renovations, kids’ private school fees, and lavish travel habits only made possible by high incomes, they are deeply worried about what happens once the pay cheques stop.

That tension - the onslaught of high taxes and uncertainty in the rules - is exactly what makes retirement planning so difficult today.

Why we’re launching the Livewire Retirement Series

That is exactly why we’re launching the Livewire Retirement Series.

By 2030, all Baby Boomers will turn 65, and in Australia, there's over $5 trillion at stake in terms of wealth to be spent or passed on over the golden years. Gen X and Y aren't far behind, with many entering their 50s and 40s, respectively.

Commencing tomorrow, we’ll publish a series of high-quality interviews and wires with some of Australia’s leading retirement specialists, portfolio builders and wealth advisers - tackling the biggest questions investors face as they move from accumulation to decumulation.

The contributors include:

• Melody Edwards from Evalesco, sharing practical steps you can take in the final decade before retirement.
• Adam Dawes from Shaw and Partners, with a portfolio construction masterclass and top ETF ideas.
• Rebecca Hurford from Infocus Australia, on tax strategies that could save wealthy Australians hundreds of thousands.
• Dr Don Hamson, on the role Australian equities still play as a retirement income pillar.
• Laurence Parisi of Trilogy, who emphasises the focus on a balanced portfolio, with income and growth, risk and stability, and short-term certainty with long-term sustainability.

Because whether you’re five years from retirement or 25, one truth remains undefeated: 

You’re going to retire one day - don’t be stupid enough to do it broke.

I know plenty of people on $300,000 to $400,000 household incomes, still 10-15 years away from retirement, with no meaningful assets, holiday debt, and super balances that are beyond embarrassing given what they earn.

Once the rivers of gold from employment stop, they are in for a very, very rude shock - an old age defined by miserable austerity - a fate I’d like you to avoid.

Get involved and win a Livewire hat!

We’d love your input throughout the series.

We are giving away free Livewire hats for great comments; whether they are thoughtful remarks, relatable stories or fantastic questions - which we will happily try and get the pros to answer - so please drop your thoughts on the articles/videos as you see them. I will read each one of them.

Most of all, enjoy our Retirement Series - you will learn a lot from it.