Learning How to Stay Rich

The Two Games of Money: Why Your Best Strength is Your Greatest Blind Spot

You're an optimist and a builder, you're wired to chase opportunities and grow your wealth - and who doesn't like that. But what if that very superpower is the crippling blind spot that stops you from protecting everything you've built? Getting wealthy is one thing, staying wealthy is another game all together

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Some of My Favourite Kinds of People

I recognise you.

I see you in my office, on our Zoom calls, and occasionally at networking events. You’re the entrepreneur and business owner and builder who is always building something from nothing. You're either a professional who’s at the top of their field, or a small business Tradie, with a killer idea and great new service, filling a need. Either way, you're probably doing the work of five other people and constantly changing hats.

You’re an optimist. I mean you have to be. You’re wired to see opportunities and deals where others see risks and random disconnections. You know, deep in your bones, that you will succeed against the odds, that's what you do.

And to be honest you’re probably one of my favourite kinds of people to work with.
We’ll talk for an hour about your business. We’ll map out growth strategies, investment opportunities, and ways to build your wealth. You might be using a SMSF. You might be using a partnership structure to leverage opportunity, or you might be building a new market. The energy is electric. It’s all about offense. It’s about ' what could go right?' and connecting the dots everyone else missed.'

Then, the conversation shifts gears.

I’ll gently ask, ' Okay, that’s the growth plan. Let’s talk about the protection plan. When did you last update your Will document and is your Company Power of Attorney in place?'
And with that question the air gets sucked out of the room.

Sometimes your eyes glaze over. You’ll shift in your seat. You’ll look at the ceiling. You’ll laugh and say, 'Oh, God, I’ve been meaning to do that for years. It’s on the list.'
Then I’ll ask, 'And your life and disability insurance - who are they with? If you couldn’t work for the next six months, how long would the business survive?'

And just like that, the high-energy visionary is replaced by someone who’s a little tired, a little guilty, and very keen to change the subject.

If this feels familiar to you, take a deep breath: you're not lazy, you’re not irresponsible, and you’re not failing. You're probably working exactly as our evolutionary wiring expects and you’re just trying to play two completely different games at the same time, using the wrong set of rules.

The Tale of Two Games

In my years of working with small business folks, I’ve come to see that building a successful life requires you to master two different games. The problem is, the skills that make you a superstar in the first game are the exact same skills that will make you fail miserably at the second.
Let me show you how that happens.

Game 1 is The ‘Getting Rich’ Game.

This is the game of Offense. This is your world.

• The Goal: Accumulation and Growth
• The Feeling: Excitement, stimulation, ambition
• The Mindset: 'What could go right?'
• The Actions: Chasing opportunities, researching investments, building the business, taking calculated risks.

This is a high-feedback game. When you do something right, you get an immediate reward. A new customer signs on, you become a favoured supplier, your revenue target is hit. It’s a dopamine-driven world, and it feels fantastic.

To win this game, you must leverage your Optimism Bias (that very human tendency to overestimate the likelihood of good events occurring and underestimate the likelihood of bad events occuring). I don't believe it's a flaw, but rather the essential fuel of an unshakeable belief that you’re more likely to succeed, than fail. I know it's not ignorance; I’d describe it as being more ‘hyper focused on what's needed now’.

Without it, you’d never have started your business. You’d never have taken the risks that got you here. It is the single most important mental tool for playing offense.

Game 2 is The ‘Staying Rich’ Game.

This is the game of Defense. This is the world you avoid.

• The Goal: Preservation and Protection
• The Feeling: Prudence, humility, responsibility
• The Mindset: 'What could go wrong?'
• The Actions: Setting up a Will document, establishing life disability insurances, creating Powers of Attorney, having tough conversations

This is a low-feedback game. When you do something right - like pay your insurance premium or sign your estate plan - you get... nothing. Just quiet. Clearly, there’s no dopamine hit and no immediate reward. Sure, it's a feeling of relief your future self will thank you for, but just not today. It’s about preventing a future catastrophe, not creating a present win. It’s a cortisol-driven world, designed for vigilance, not excitement.

When Optimism is the Wrong Tool for The Job

And here is the critical, life-altering truth: The Optimism Bias that makes you win Game 1, is catastrophic in Game 2.

• It’s the right tool for the wrong job.

When you try to play the Game of Defense, your world-beating optimism becomes a crippling blind spot. It shields you from the very risks you need to see.
It whispers:

• 'You’re healthy. You don’t need to think about disability insurance yet'
• 'You’re not going to die anytime soon. The Will can wait'
• 'Your business partner is your best friend. You don’t need a formal buy/sell agreement'
• Your greatest strength becomes your greatest liability. It stops you from planning for failure, and in doing so, it leaves the entire empire you’re building, your business, your family’s security, your legacy, unprotected- and standing on a foundation of sand

Rule #1 The First Step to Wealth is Not Getting Wiped Out

We are taught to build, to grow, to play offense. But the first, most important, and most often-missed step in getting rich is not getting wiped out. You must build a rock-solid backline before you can rely on your star full-forward to kick the winning score.

The 'Staying Rich' tools - the Will, the insurance, the legal agreements - are the concrete foundation. The 'Getting Rich' game is the awesome house you build on top of it, but optimism bias is pushing you to build the house first, and it’s a fatal mistake.

So, how do we fix this? How do we tame the very mental bias that makes us successful?
We can’t kill off our optimism; we all need it to get out of bed in the morning. And the solution isn’t to become a dark pessimist either. The solution is to become a professional.

A professional athlete knows when to play offense and when to play defense. You have to learn to do the same. You have to consciously and deliberately change your mindset. Here are the practical steps to building your defense.

1. Name the Game You're Playing Today

You cannot play both games at once. The mindsets are incompatible. The first step is a simple awareness - when you find yourself avoiding a task, just pause and name it.

• 'Oh, I’m avoiding this. This is a Game 2 (Defense) problem'

That simple act of naming it (out loud even) creates a mental space. It separates the task (signing a document) from the feeling (dread, boredom). It’s no longer a vague cloud of 'stuff I don't want to do', it's a specific, defined task that you’ve identified as part of your defensive strategy.

2. Schedule Your 'Game 2 Huddle'

Don’t try to learn about the essentials of Will documents on a Tuesday afternoon between a sales call and a client meeting. Your brain will be in full-on 'Offense' mode, and you’ll fail.

• You must schedule a specific, separate time to play defense.

Put it in your calendar just like you would a sales meeting. Call it 'Risk Planning' or 'Legacy Strategy.' This is your 'Game 2 Huddle.' It’s a 90-minute block where you give yourself permission to take off the optimist's hat and put on the pragmatist's hat. In this huddle, your only job is to ask the hard question: 'What could go wrong?'

3. Run the 'Pre-Mortem' Exercise

Your Optimism Bias makes it hard to imagine a negative future. So, let’s trick it. This is a powerful exercise I do with all my business-owner clients. Instead of asking, ' What might go wrong?' we do a 'pre-mortem.' We assume it already has.

I want you to sit in your ' Game 2 Huddle' and write down the answers to this: 'It’s one year from today, and my life is in ruins. What happened?'

This future-pacing exercise short-circuits the optimism bias. It gives your brain permission to find the cracks in a successful situation, without feeling like it’s being disloyal to your goals. The answers that come out are often brutally honest and incredibly clarifying.

• 'I had a car accident, I couldn't work and I had to drain the business cash to pay for surgery and rehab. The business ran out of operating cash in 60 days.'
• 'My business partner had to unexpectedly exit the business, and we had no written partnership agreement, so I was forced to sell the business to pay him out.'
• 'I died, and my spouse, who knows nothing about the business, was left to deal with the chaos.'

Kudos. You’ve just found your defensive priority list.

4. Reframe the Win

In Game 1, the 'win' is a feeling of excitement. In Game 2, the 'win' must be a feeling of responsibility.

• This is the most important mindset shift you can make.

Paying your life and disability insurance premium isn't a 'cost.' It’s not a 'loss.' It’s an act of love. It’s you, today, protecting your family in a future you’re not in.

Signing your Will isn't 'planning for death.' It’s about creating a future peace for tomorrow and a calm for today. It's the final and most profound act of care you can show, so you don’t leave behind a legacy of chaos (and legal bills) for the people you love most.

You have to find a new 'why.' You’re not doing this because you’re afraid; you’re doing this because you’re responsible.

Your Legacy is a Resilient One

Being a successful entrepreneur or business professional isn't just about your offensive stats. It’s not about your revenue or your growth rate. That’s just half the scoreboard.

A true professional, a true leader, is someone who builds something that lasts. Something that is resilient. Something that can take a hit and keep standing and something that doesn't leave your partner without a protective roadmap to follow, if something unexpected happens to you.

Building your defense - your Game 2 strategy - is what gives you the freedom to play offense with true confidence. It’s the act of a professional who understands the whole game, not just the exciting parts. It’s the ultimate expression of care for your business, your team, and your family. So, I see you. I see your drive and your optimism. It’s your superpower.

Don’t let it be your blind spot.

Is it time to book your Game 2 Huddle with me? You do the hard, quiet work of building your foundation. Offense might win headlines, but I’ll work with you to build your defence, that builds a legacy.

Frequently Asked Questions: The Two Games of Money

Drew Browne is a specialty Financial Risk Advisor working with Small Business Owners & their Families, Dual Income Professional Couples, and diverse families. He's an award-winning writer, speaker, financial adviser and business strategy mentor. His business Sapience Financial Group is committed to using business solutions for good in the community. In 2015 he was certified as a B Corp., and in 2017 was recognised in the inaugural Australian National Businesses of Tomorrow Awards. Today he advises Small Business Owners and their families, on how to protect themselves, from their businesses.  He writes for successful Small Business Owners and Industry publications. You can read his Modern Small Business Leadership Blog here. You can connect with him on LinkedIn.  Any information provided is general advice only and we have not considered your personal circumstances. Before making any decision on the basis of this advice you should consider if the advice is appropriate for you based on your particular circumstance.