The Last Question You Should Always Ask First

The last question you should ask first

Your biggest financial decision has a blind spot. Here’s how to fix it.

Checking your personal insurability isn't the last step in a big decision - it's the first.

It's a uniquely Australian ritual. Every few years, the north-eastern coast of Australia is either devastated by catastrophic floods one year, fires seemingly the next. Lives, homes and businesses are swallowed up by churning brown water or burnt beyond a crisp. The media descends. We hear the same questions on a loop: “Why do people still build here?” and “Why do businesses still stay here?” and inevitably, “Don’t they know it’s a flood zone?’”

But they always miss the real question, the one that truly matters: What happens when you become uninsurable?

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The uncomfortable truth of facing personal uninsurability

We acknowledge this uncomfortable reality and understand almost instinctively, that a postcode can become uninsurable. A line gets drawn on a map, and suddenly, the risk is too great to insure. The safety net is gone.

But here’s the uncomfortable truth we never talk about: that same crisis doesn’t just apply to postcodes. It also applies to people.

You can have your own personal flood zone. The scary part? You won't hear a weather warning. You won't see the storm clouds. You’ll just feel the water rising around your ankles when it's already too late.

Think of it as a ticking clock in your own biology. One unexpected medical diagnosis. One shift in your family's medical history and the alarm goes off. Suddenly the line isn't on a map. It’s drawn around you. The door slams shut. You’ve become uninsurable.

And if that happens the day after you’ve just signed the mortgage, launched the business, entered the partnership, purchased the franchise or guaranteed that loan? There’s no appeal. You've just locked yourself into a risk you can no longer transfer. You've built your dream on a flood plain, and the rain has started.

The cost of convenient silence

In my work as a specialist risk adviser, I see the aftermath of this conversation avoidance every day. I see smart, ambitious people - business owners, families taking on a new mortgage, partners buying into a venture, perhaps a franchise or an exciting opportunity, intended parents going through the process of IVF or even choosing a surrogate, who did everything right, except for one thing. They never asked the first question first: “Am I insurable?”

The unasked question: Why (some) advisers stay silent

Why others seem content to avoid this conversation, I believe it's the most foundational one we're not having. It's time for a mature honest look at the question you can't afford to ask last: what happens when I become uninsurable?

Were you properly guided to have this type of talk about managing your personal risks when you became a newlywed, a joint mortgagee, a business partner, a franchisee, a parent lending the deposit for a house to an adult child, or even an intended parent or surrogate? If the answer is no - if you weren't pushed to explore this fundamental question - then you haven't just been poorly advised. You've been critically under-advised.

Why is this conversation so often avoided? Let’s be blunt. For many in the financial world, the primary focus is on wealth accumulation. Paying for insurance premiums can mean less money to invest, and if an adviser’s fees are tethered to the level of funds under management... well, you can see their silence is profitable.

Let's be clear. Is your financial plan an actual plan? Or is it just a high-stakes gamble you haven’t admitted to yourself?

A financial plan that ignores personal risk isn't a plan. It’s a gamble. Failing to have this hard conversation isn't a minor oversight; it's a critical failure of advice.

Put another way, it’s like seeing a doctor for pounding headaches but they never once take your blood pressure - well, you know where I’m going. You haven't just been poorly advised; you've been critically under-advised.

Life’s wicked problems

This critical failure of risk advice has profound implications when we consider the emotional and financial outcomes of managing our personal risks.

In our personal lives, the most difficult risks are those that have both emotional, and financial, consequences. These wicked problems, if you like, inevitably cloud our judgements and plead for special leniency and forgiveness, when things ‘don't work out as they were expected to’. While the focus of a financial plan often remains on wealth, the true measure of a sound plan lies in how it addresses these 'wicked problems' that overlap life, love, and business.

Let's take a hard look at the real life issue of suddenly finding out you're either uninsurable (or hard to insure), and how that affects the management of your personal risks in life, love, and business.

Most people agree successful life and business decisions revolve around good timing and getting the decision sequence right. Many optimal life and business decisions hinge on knowing the right sequence of steps, much like making good coffee.

For business owners, and their families making crucial personal decisions, how does this important conversation begin when you're considering a new business venture or partnership?

How does this look for a double income family looking to have a double mortgage through the purchase of an investment property? And for folks going down the SMSF route, what are the right questions to ask, before you sign the paperwork and become the Director's of a Corporate Trustee company, first?

Two foundational questions your adviser expects you to have asked yourself

Banks deal with you on commercial terms - expecting you have carefully considered ( been advised, even) about the consequences of your decisions with them, just in case life doesn't work out the way you hope. Read the fine print in any home loan agreement and you'll see you're required to keep your property appropriately insured for the term of the mortgage debt - against fire and floods.

So here are two hard questions, one commercial one personal, you’d want to have hard answers for.

1. What's the risk management sequence you need to follow as you consider your next big adventure?
2. What level of personal courage is required for you to disengage, professionally or personally, from situations where you later find out the risks are actually unmanageable, or unusually high, compared to the promised rewards?

Managing - not avoiding, the risks of life (love) and business

Let's return to the basic components of managing life and business risks, and in particular those personal risks that seem to ‘overlap’ each other, that affect us all each day.

You can't avoid risk, so manage it

Life and business is all about managing our risks - not necessarily avoiding them. And while these two areas of our life overlap, we cannot forget the reality of how love and relationships intertwined with our life and business, and so deserve special respect and attention, also.

Risk management is a ceaseless, evolving art. Today, crossing a busy road demands a double-check while navigating a footpath now requires a new 'dance step,' thanks to the omnipresent home food delivery scooter service.

So, how do you manage a risk you can’t fully control? Most risk management frameworks feel like they were designed by a committee to be ignored; more a weapon for the company HR Department, not a practical tool for your life. They become an exercise in strategic avoidance.

A simple framework for a complex problem

Let’s simplify it. When it comes to the big, life-altering risks - the ones with both emotional and financial fallout - you have four choices.

• Avoid Them: Some risks aren't worth taking. (Probably not an option for starting a family or a business).
• Accept Them: You could cross your fingers and hope for the best. (A terrible strategy for anything you can’t afford to lose).
• Manage Them: This is for everyday risks, like insuring your car.
• Transfer Them: This is the one that matters the most. For the catastrophic risks in life and business; a sudden illness, a disability, a death, those outcomes too great to bear alone, you transfer them. You shift the financial burden to an insurance company whose entire business is built to carry it for you.

The real hurdle isn’t the insurance policy premium, but rather your hopeful disbelief that it could ever happen to you.

This mistake is more common than you think

This costly mistake isn't limited to a specific type of person, budget or postcode; in fact, the tendency to overlook this foundational step is very widespread.

Who's at risk? Everyone with something to build, something to protect, or a life in motion.

This isn’t a niche problem for a handful of people. The risk of becoming uninsurable hangs over us all; anyone making a significant financial or life decision.

We can group them into three main categories:

• The Builders Anyone taking on new debt to create something new. This is you when you're finally launching that business, signing the mortgage on your first home or an investment property, securing a commercial loan, buying into a partnership or franchise, or developing your first property. For The Builders, while debt is the fuel for growth, your personal insurability is the foundational ground you build upon. Without it, whatever you’re building (and with whom), is at risk.
• The Protectors Folks making significant moves to secure their families’ future. This is you when you're lending money to your children for a home deposit, acting as a guarantor on a loan, or setting up buy/sell agreements to protect your business partners. It’s you navigating the unique emotional and financial challenges of IVF or surrogacy, or carefully blending the finances of a new family after a remarriage. For The Protectors, every move is about creating a safety net for the people you love. But a net with a hole in it from the start catches no one.
• The Transitioners People whose lives are in a state of change. This is you when you’re changing careers, escaping the perceived safety of a corporate job to go out on your own, or untangling the financial complexities of a divorce. It’s you planning for that hard-earned retirement (whatever that looks like today), or dealing with the financial reset that comes from being made redundant. For The Transitioners, every major change in circumstance represents a new chapter - and a potential fault line where your insurability can unexpectedly crack.

By now you can see the sheer scope of this necessary, yet absent conversation; the one that truly matters: What happens when you become uninsurable?

Are you too close to your problem?

People defer the question of their insurability until the eleventh hour, often, after months of sunk costs. Insurance becomes a grudge purchase, the last box to tick. Then comes the final, unwanted answer: "No." In the deafening silence, the sunk cost fallacy takes hold, and the desperate plea of "we've come too far" begins to defy financial gravity.

How certain are you that you can manage the risks sufficiently?

When it comes to taking risks and the question of, ‘how much is too much,’ this is a personal question we all must answer ourselves. Human nature reminds us, being too close to a problem, even a bystander to a complex situation, can raise fair questions about our own loss of perspective and simply ‘being too close’ to see the forest for the trees. And who wants to have a difficult conversation anyways?

The conversations we have, and the conversations we avoid, all help frame how we see the world around us. When we habitually avoid these types of questions, we also avoid developing the skills to have them and learning how to integrate them into our life, rather than being frightened about their presence in our life.

Avoiding these conversations allows a problem to loom too large to the point the problem we talk about feels simply too big, so we become apathetic about it and unconsciously look for ways to avoid it.

What we do know is that those risks that have both emotional and financial consequences are doubly compressed and equally dangerous. A life well lived is about how you manage those risks with intentionality. Some risks in life and business are simply too big to carry alone. Using life and disability insurances to carry them for you and your family (and your business) is not about fear; it is about smart planning.

Remember: It's not the cost that's the biggest obstacle; it's the quiet hope that ‘it won’t happen to you’.

The first step is to take control by asking about your insurability. The second is to act on that knowledge and ask yourself, ‘ok what now?’

It's the difficult conversations that allow you to build a safer future for your family and business on purpose, ensuring the life you are creating is built to last, and not become the expensive casualties of a last minute check, ‘hey, can I get insurance for that?'

The Unasked Question and the Unexpected Answer

Too often, I see people at the eleventh hour of a deal. They’ve poured months of time, money, and emotional energy into a project. The insurance is the last box to tick, a ‘grudge purchase’ to placate a bank or a partner, or the nagging accusatory voice in the back of their mind.

Then comes the unwanted answer with a burning sting of comprehension: "No."
The silence that follows is deafening.

In a desperate attempt to avoid the gut-wrenching question, ‘Should we still proceed?’ a dangerous cognitive bias then kicks in: the sunk cost fallacy. You hear yourself saying, "But we've invested so much to get this far..." as if that emotional plea could somehow defy financial gravity.

Suddenly our relationship with good sense seems unusually strained and we begin the mental gymnastics of trying to justify what in other times we would point to as high risk and questionably acceptable.

But not now; not for us; maybe.

This isn't about fear; it's about foresight. It's about demonstrating grace under pressure by having the difficult conversations before they become desperate ones. Building a business, a partnership, or a secure future for your family is about getting the sequence right.

Don't wait until you're standing on the riverbank to ask if the ground is stable. Ask the hard question first. Find out if you’re insurable. Because the life you are building deserves to last. It deserves to be built on solid ground, not on chance.