There’s a scene in The Gambler where John Goodman sits across a table and lays out, with terrifying clarity, what it means to be free. It wasn’t wealth, luxury, lifestyle, or a number in a bank account. He talks about being in a place where nobody can make you do anything you don’t want to do.
He calls it the level of fuck you.
I first saw that clip on Instagram some time ago, scrolling late at night the way we all do when we’re too tired to sleep. I watched it several times. Then I thought about it. I realised I might have already stumbled into that sweet spot without realising it. And I hadn’t planned any of it.
The Wrong Question
Most of us spend our working lives asking the same question: How much money do I need before I can stop?
It’s a common question. It’s also a trap.
The number is always moving. You hit it, and the goalposts shift. The market dips, and suddenly you need more. Your lifestyle creeps upward, and the number creeps with it. You talk to a financial planner, and they run projections based on assumptions that make you feel sick. “How much? To retire?” You lie awake at night running your own calculations, and the answer is always “not yet.”
I know of people who earn three times what I ever did and still don’t feel like they have enough. Superannuation balances that would make you blink. Investment properties. Diversified portfolios. And they’re still afraid. Still grinding. Still tolerating what they shouldn’t have to tolerate.
“Enough” isn’t a number. It’s a feeling. And you can chase that feeling for your entire working life without ever catching it.
The question that matters should be: Who has leverage over me right now, and how do I start removing it?
That you can act on. Today. At any age.
How I Stumbled Into Retirement
I spent more than a decade in my twenties and thirties moving from job to job until I landed a position at a little-known automotive dealership. Over the next 10 years, I did good work, increased sales by some 800%, and was well paid for it.
Then we migrated to Australia and started over from zero.
Here, after spending 7 years at a small training and consulting firm, I was convinced that “a job” would never lead to financial independence. At a third of what I used to earn, I could see clearly that the light at the end of the tunnel was an oncoming train. So I decided to start a business, which meant taking on a substantial loan to build and own a commercial kitchen. The restaurant closed after 5 years. But I was lucky with the commercial kitchen we built. It now returns a decent rental yield.
Arse luck, I always say.
What happened in Australia was mostly luck. Through a combination of decisions that turned out better than expected, I came out on this side with very manageable debt and enough passive income to live on. The current trajectory looks good; the grind was over. Nobody had leverage over me.
At 60, I had accidentally stumbled into retirement.
It took me a while to realise it. For a long time, I kept running numbers in my head, awake at night, stress-testing scenarios. What if the property market drops? What if I’ve made a bad purchase? But I realised that the anxiety wasn’t about money. It was about the loss of forward motion. For thirty-something years, earning had been proof that I was still in the game. Without it, I felt vulnerable.
When I finally asked the real question (does anyone have leverage over me?), the answer was obvious. Nobody did. I was free.
I just couldn’t feel it, because I was still stuck in the old mindset.
What I’d Do Differently
Here’s the part that keeps me up at night now. Regret.
If I had my time again, I would have started this at thirty. Maybe earlier. I would have been deliberate about building the position instead of arriving at it by accident. I would have worked backwards from the condition in which nobody has leverage over me, rather than forward to an elusive number that was never going to feel like enough.
I wouldn’t have needed luck if I’d had a plan.
Luck flatters, but it’s unreliable. Too many did everything right by the old rules: earned well, acted responsibly, showed up. Yet they remain trapped and afraid, still working at sixty because they asked the wrong question too late.
I got lucky. They deserve better than luck.
The Framework: Dismantling Leverage
If you’re in your fifties now (or earlier), with ten or fifteen productive years ahead of you, here’s the reframe that could change everything: stop chasing a retirement number. Start auditing your dependencies instead.
Leverage means having something or someone with power over your decisions. It’s not a vague feeling of insecurity; it’s a clear list of forces, relationships, debts, situations, that, if disrupted, would force you into choices you don’t want to make. You can identify them. You can name them. And once they’re named, you can start dismantling them, one at a time.
Income dependency. Does everything in your life collapse if you lose your job? For most people, the answer is yes. One income source. One employer. One decision-maker who could end your financial security with an email. That’s leverage. The question isn’t “how do I earn more?” It’s “how do I build another source of income, even a small one, that doesn’t depend on the same person or institution?” It doesn’t have to replace your salary. It just has to exist. A rental property. A consulting side practice. A digital product. A weekend gig. Something that proves to your nervous system that you have options.
Housing dependency. Does your landlord have leverage over you? Does your mortgage lender? When you rent, someone else controls the roof over your head. They can raise the price. They can sell. They can choose not to renew. When you carry a large mortgage, the bank has leverage. You can’t afford to earn less. You can’t afford to take a risk. You can’t afford to stop. The path toward owning your home outright, as boring and unglamorous as it sounds, is one of the most powerful leverage-removal moves you can make. Nobody can take the roof from over your head when it’s yours.
Lifestyle dependency. Have you built a life that requires peak earning to sustain? This one is sneaky because it happens so gradually. The nicer car. Another car. The private school fees. The holidays that got a little more expensive each year. The subscriptions, the gym membership that you never really use, the upgrades. None of them felt like a big decision at the time. But together they’ve built a life that requires a substantial income to maintain, and that requirement is leverage. The question is: what could I cut now without losing anything that actually matters to me? You might be surprised by the answer.
Debt dependency. Are you carrying obligations that lock you into earning at a certain level? A car loan. A caravan loan. An investment loan. Credit card balances that somehow never quite cleared. Each one is a leash. A link. The kind you stop noticing because you’ve been on it for so long. Every debt you clear removes a link. Every link you remove gives you room to breathe, to choose, to say “fuck you.”
Identity dependency. This might be the most dangerous of all. Have you built your entire sense of self around your job title, your industry, your professional reputation? What happens to you, psychologically, if that role disappears? Replaced by an algorithm? Outsourced? I’ve watched people fall apart not because they ran out of money but because they ran out of identity. The paycheque wasn’t just income. It was proof of who they were. What they’re worth. If you can’t answer the question “Who am I without my job?” you’re carrying a dependency that no amount of money can resolve.
This isn’t a financial plan. I’m not a financial planner. Think of it as a kind of diagnostic. A way of looking at your life and asking, honestly, where are the leashes? Where are the things that have a hold on me, that would force me into a corner?
Name them. Then start working on them. One at a time. Deliberately.
The Paradox
Once you’ve dismantled the leverage, once you’ve reached the position where you could genuinely walk away from anything that has a hold on you, something unexpected happens.
You might not want to leave. Your job. Your situation.
The job that felt like a prison? It becomes tolerable the moment it becomes a choice. The boss who drove you crazy? Less infuriating when you know you could hand in your notice tomorrow and your life would be fine. The grind that was slowly killing you? It’s just work, once it’s no longer compulsory.
The “fuck you” money isn’t really about saying fuck you. It’s about never needing to. It’s the quiet confidence that comes from knowing you have options. And that confidence changes everything: how you carry yourself, how you negotiate, how you respond to pressure, how you sleep at night.
I suspect that many people who reach the position will choose to keep working. Just differently. On their own terms. For their own reasons. Because they want to, not because they have to.
That’s what freedom actually looks like. Not endless days at the beach. Not a golf course. Or Business-class vacations. Just the absence of compulsion.
Start Now
“The best time to plant a tree was 20 years ago.
The second best time is now.” - Old Chinese Proverb.
This conversation should start at thirty. Build the structure early, when time is on your side, and the compounding works in your favour. If I could go back, that’s what I’d do.
But if you’re fifty, you have ten or fifteen years. There’s still time. Enough to clear the debts. Enough to build a second income stream. Enough to right-size a lifestyle that may have crept beyond what you actually need. Enough to start answering the question of who you are if you lose your career tomorrow.
If you’re sixty, you have less time but more clarity. You know what matters. You know what doesn’t. Use that.
The worst version of this story is the one where you arrive at retirement age with no position, no plan, and no choice. Still dependent. Still afraid. Still hoping the number will be enough.
It won’t be. Because it was never about the number.
Start dismantling the leverage. One at a time. That’s the art of “fuck you” money. And that’s what The Second Act is about.