I wore golden handcuffs for the better part of three decades and thought they were proof I'd made it. Group CISO at Standard Chartered Bank, S&P Global, Qantas Airways, IBM. The compensation packages got bigger at every move: base salary, equity, annual bonus, pension contributions, long-term incentives. Every new offer felt like validation that the system valued me.
It took an embarrassingly long time to realise the system wasn't valuing me. It was pricing me. There's a difference, and it matters more than most executives want to admit.
The trap is not the salary
When people talk about golden handcuffs, they usually mean the money is too good to walk away from. That's not quite right. The salary is not the trap. The trap is what the salary has done to your identity, your dependency, and your ability to imagine a life that isn't funded by someone else's payroll.
You can earn $400,000 a year and still be financially fragile, because if the income stops, everything stops with it. That is not wealth. That is a high-paying dependency.
Most executives I work with have spent 20 or 30 years building impressive careers and have almost nothing that generates income without their direct involvement. They have savings, sure. They might have some shares vesting over the next few years. But if you asked them to maintain their current lifestyle for 18 months without a salary, most would start sweating within the first quarter.
You are running your life like a P&L statement
Here is the shift that changed how I think about money, and it comes down to two financial statements every executive already understands from work but has never applied to their own life.
A P&L statement (profit and loss) tracks revenue in, expenses out, and whatever is left over is your margin. Most executives run their personal finances exactly this way. Salary comes in, mortgage and school fees and holidays go out, and whatever survives gets parked in a savings account or super fund. The entire model depends on revenue continuing to flow, which means it depends on you continuing to show up.
A balance sheet measures something different. It measures what you own that holds value and generates returns independent of your effort. Property that produces rent. A business that runs without you in the room. Intellectual property that sells while you sleep. Content libraries, digital products, licensing agreements, equity in ventures you helped build.
A salary is a line on the P&L. It measures activity, not worth. Assets are the balance sheet, and they measure what works whether you show up or not.
If you have been in corporate for 20 years and your balance sheet is mostly your house and your super, you have been running a P&L life. High revenue, low asset accumulation. The business equivalent would be a company turning over millions with nothing on its books, and no investor would touch it.
My dad understood this better than any CFO I've worked with
My father worked in a foundry. Hard, physical work. But he also ran an ice cream van on weekends and evenings, and he owned rental property. He built redundancy into his income the way an engineer builds redundancy into a bridge.
If the foundry shut down, the ice cream van still ran. If the weather killed ice cream sales, the property tenants still paid rent. He never used the language of portfolio theory or diversification strategy. He just understood, from lived experience, that depending on one source of anything was a structural weakness.
Daniel Priestley puts it simply: income follows assets, not effort. My dad lived that principle decades before anyone wrote a business book about it, and it took me three decades of climbing corporate ladders to remember what he'd already shown me.
The irony is that executives are trained to think in terms of risk management, redundancy, and contingency planning at work. We build disaster recovery plans and business continuity frameworks. Then we go home and bet our entire financial life on a single income source controlled by someone else. We would never let a business operate with that kind of concentration risk, but we accept it in our own lives without question.
What is your actual freedom number?
Kristy Shen introduced the concept of the freedom number, and it is worth every executive doing this calculation properly. Your freedom number is not just a target portfolio balance. It starts with understanding your burn rate: your annual expenses minus any passive income you already have.
Most people skip straight to "how much do I need invested?" without first getting honest about what they actually spend. So start there. What does your life cost per year, with nothing cut? Include the mortgage, the school fees, the insurance, the holidays, the subscriptions, all of it.
Now subtract any income that would continue even if you stopped working tomorrow. Rental income, dividends, business revenue that does not require your presence. For most executives, that second number is close to zero, which means their burn rate and their total expenses are almost identical.
That gap between your expenses and your passive income is the problem you need to solve, and a bigger salary does not solve it. A bigger salary just increases the P&L revenue line while the balance sheet stays empty.
The shift from P&L to balance sheet thinking
Making this shift does not mean quitting your job. I am not suggesting anyone hand in their resignation on Monday. What I am suggesting is that you start allocating time, energy, and capital toward building assets alongside your career, rather than waiting until you leave to start from scratch.
This means asking a different question. Instead of "how do I increase my salary?" the question becomes "what can I build or buy that produces income without me?"
The answers will vary. For some executives, it is property. For others, it is a digital product or an online education business built on their professional expertise. Some will build a consulting practice that can eventually run with a small team. Others will invest in or acquire small businesses.
The specific vehicle matters less than the principle: every dollar and every hour you put toward an asset moves you from P&L dependency toward balance sheet strength. Your career becomes one income source among several, rather than the only thing between you and financial trouble.
What this looked like for me
While I was still in corporate, I co-founded the Cyber Leadership Institute. It started as a side project, built on expertise I had developed over decades as a CISO. Over time, it became a seven-figure business. When I eventually left corporate in 2025, I did not jump into the unknown. I stepped onto a foundation I had already built.
That is the difference between an exit and a collapse. An exit is planned, funded, and supported by assets that were already producing before you walked out the door. A collapse is what happens when someone leaves a high salary with nothing underneath them.
My dad would have called it common sense. I call it balance sheet thinking, and I wish I had started a decade earlier.
Three questions to ask yourself this week
If you are a senior executive reading this, you do not need a full financial plan today. But you do need to get honest about where you stand. Here are three questions worth sitting with:
- If your salary stopped in 90 days, how long could you maintain your current life? Not a reduced version. Your actual life, with all its current costs.
- What do you own right now that produces income without your involvement? Be strict with this. Shares that might pay dividends someday do not count. What is actively producing cash flow today?
- In the last 12 months, how many hours did you spend building an asset versus earning a salary? If the answer is zero hours on assets, you have been running a pure P&L life, and the balance sheet is not going to build itself.
These are not comfortable questions. They were not comfortable for me either, especially when I realised that years of six-figure salaries had produced almost no independent income-generating assets. But discomfort is where the shift starts.
Salary is a tool, not a destination
None of this is an argument against earning a good salary. Thirty years in corporate gave me the expertise, the credibility, the network, and the capital that made everything else possible. The salary funded the assets. The career built the authority. I would not trade that experience.
But a salary that funds nothing except lifestyle is a salary on a treadmill. It feels like progress because the numbers go up, but the balance sheet stays flat. The goal is not to stop earning. The goal is to make sure that what you earn is building something that lasts beyond your next employment contract.
Your salary is not wealth. It is revenue. And revenue without assets is just a high-paying job with an expiry date.