How I turned a loose 20-year plan into a self-sustaining system for freedom.
Financial Pragmatism in Practice
Most people think early retirement is about money. It’s not. It’s about time, direction, and designing a life you can live deliberately.
This piece opens my series Financial Pragmatism in Practice — essays about how structure, awareness, and patience can turn long-term goals into reality.
The Real Reason Behind the Plan
When I think about the last twenty years, I don’t see a story about money. I see a story about freedom. About designing a life that lets me work on what I love, on my own terms, without waiting for permission.
From the outside, it might look like a financial success story: pay off debt, invest wisely, retire early. But that was never the real point, it’s much more than that. The real goal was to get back to creating — to write, build software, and make films — while I was still young enough to do it with energy and focus. I wanted to finance it myself so that no one else could control what I made or how I made it. That was the quiet motivation running underneath everything I did.
A Loose Plan That Became a System
When I first started, I had what you could barely call a plan. I wrote down a few ideas:
- Pay off my debt.
- Learn how to invest.
- Build a portfolio large enough to live off for the rest of my life.
- Retire early and focus on the creative work I put on pause.
That was it. No detailed spreadsheets, no step-by-step map, just direction. I didn’t know how I’d do it. I only knew I had to start. I had a vision forming, a plan taking shape, and the focus to see where it could lead.
Paying off debt came first. I could see how much mental stress disappears when you stop owing money. It creates space to think clearly. That clarity turned into momentum which I used to study investing.
I studied thinkers who understood patience, simplicity, and discipline. At first it was about copying them. I’ve always loved accumulating knowledge — connecting ideas across fields until patterns start to reveal themselves. When I started my first business, it was the same instinct: merging technology, design, and philosophy to build things people were looking for before they became mainstream.
Over time, I wasn’t just learning what these thinkers did, but how they thought: how they handled uncertainty and built systems that outperformed over time. I would eventually develop my own philosophy of money, one that matched my temperament and goals.
Somewhere halfway along that journey, I stumbled across FIRE, which stands for Financial Independence, Retire Early. There are thousands of articles and Youtube videos about this, and the people who live it. The concept was simple but powerful: live frugally, cut unnecessary expenses, save and invest aggressively, and buy back your time decades before traditional retirement age. Inspiring, isn’t it?
Many advocates suggested saving 50% or more of your income, investing long-term, and living on the growth. That level of saving wasn’t always possible for me — it applies more to higher-income earners. I simply didn’t earn enough to save that much. But I learned the principle behind it: the faster you grow the gap between income and expenses, the faster you buy your freedom. Over time, I found a rhythm that worked — early on, I was saving and investing between 20% and 30% of my income, consistently, for years. Later on, as my expenses and responsibilities grew, I was saving just 10-20% of my income – but the important part is how much I was able to save early on. When it comes to investing, time is your best friend.
At first, I followed the FIRE movement’s 4% rule — the idea that if you save 25 times your annual expenses, you can withdraw 4% each year and live indefinitely from your investments. It sounded simple and elegant, but as I learned more, I saw the weakness: the plan assumes the markets will keep growing at least 4% after inflation, every year, forever.
In reality, markets don’t move in straight lines. Inflation rises, cycles fluctuate, and a bad decade can easily break this model. I didn’t want my freedom to depend on optimistic math.
There are many FIRE calculators on the internet. I played with many of these, adjusting variables, playing with long-term stock market simulations, and truly understanding my current and future budgeting to more clearly see what works and what doesn’t.
That’s when I realized the system itself needed to evolve. I didn’t want to copy FIRE; I wanted to build something more resilient, something that could survive through the good and the bad.
The System Takes Shape
Armed with this new knowledge and insight, I updated the plan. My new goal became a 2% withdrawal rate, supported by a portfolio worth 50 times annual expenses — essentially doubling the stability of a traditional FIRE approach. It sounded ambitious, but it was far more realistic, secure and resilient. I called my approach SURE-FIRE.
SURE-FIRE =Secure, Uncomplicated, Resilient, Effective. A model for Financial Independence to Retire Early.
It’s more achievable than most people think if you have strong control of your expenses, foresight, and the willingness to make sacrifices today for the life you want later, while maintaining a balance between living comfortably and planning for your future.
During my portfolio-building years, while I was still employed and had a steady flow of income, my entire portfolio was structured for high-growth long-term investments compounding for 20 years. I left a portion of “uninvested cash” for a six-month emergency fund — a financial cushion in case I lost my job. It gave me breathing room to adapt, to look for new opportunities without panic.
But a year before I transitioned into retirement, the structure evolved. I kept the six-month emergency fund for unexpected events, but I also built a five-year cash reserve — enough to live on without touching my investments. That way, if the markets went through a downturn, I wouldn’t have to sell investments at a loss. I could let the system recover on its own time.
To make it work, I built multiple layers:
- A large, high-growth, long-term portion of my portfolio, for compounding over decades
- A smaller balanced mid-term portion to buffer volatility.
- And enough uninvested cash to weather any market crash without selling investments at the wrong time.
It required patience, discipline, and a lot of foresight — but it turned my plan from a financial theory into a self-sustaining ecosystem.
Redefining Lifestyle and Happiness
The financial structure was only part of the equation. The other half was re-evaluating how I lived.
To make my plan sustainable, I had to rethink what happiness actually meant — not in abstract terms, but in daily behaviour and habits. Sustainability isn’t just about having enough money; it’s about living in a way that never forces you to overspend just to feel satisfied. That required intentional spending — focusing on essentials and only keeping the few luxuries that genuinely enrich life.
Most luxuries, I realized, are traps. They look like rewards for hard work, but they quietly chain you to more work, more spending, and more dependence. The fast luxury cars, luxury vacations, big homes, and high-end gadgets. They create the illusion of progress while pulling you further from freedom.
We like to fantasize about earning a high income and see it as “making it” or “freedom,” but, most people earning a quarter of a million, half a million, or more, often fall into the same trap. As their income grows, their expenses grow to match it, a form of runaway spending. It’s easy to justify: “I’m making so much money, why not live a little?”
I’ve known people earning more than half a million a year who can’t imagine retiring before 65. Not because they can’t, but because they’ve built a lifestyle that requires every dollar. They mistake high income for freedom, but real freedom is being able to stop, and not needing permission or a paycheque to live. It’s strange how many of the wealthiest people are also the most trapped.
This isn’t just limited to people who already earn high incomes. Most people earning less than six figures still imagine that someday they’ll be making much more, so they begin inflating their lifestyle early, in anticipation of that imagined future. They buy cars worth more than their annual income, upgrade phones and gadgets annually, take luxury vacations, and convince themselves it’s normal because “one day” they’ll be able to afford it all comfortably.
That’s a dangerous illusion.
When you live as if you’ve already reached the income you hope to have, you’re borrowing against a future that might never come. As income rises, expenses rise faster. Lifestyle expands until it becomes unmanageable, and soon you’re trapped chasing higher and higher earnings just to maintain your own expectations.
It’s not always self-inflicted. You’ll always find people who encourage it – colleagues, friends, even family – they interpret your discipline as deprivation. They’ll tell you to live a little, buy a new car, buy real estate, join them on luxury vacations. They mean well, but mostly they’re trying to justify their own choices, not seeing the harmful impact it has to their own future goals.
It’s a self-perpetuating loop. The more you make, the more you spend, and the more dependent you become on maintaining that level of income. This is why so many lottery winners go bankrupt, and why high-income earners often end up living in financial instability later in life. It’s a pattern that repeats itself through history, across income levels, cultures, and generations.
I learned this early on from actually studying it, and built my decisions around avoiding it completely. I didn’t want to live as a projection of my imagined future. I wanted to live within my present reality, deliberately, without dependence on tomorrow’s income to fund today’s comfort.
Recognizing that kind of dependency — especially when you’re already inside it — takes an incredible level of self-awareness. I learned that lesson early, after my first business began to unravel. I had already reached what most would call “early success,” but I saw how quickly it could disappear beneath me. That realization was painful, but it was also a giant wake up call.
It showed me that wealth and freedom are not the same thing — and that one can easily destroy the other if you’re not paying attention.
That experience changed my trajectory. It made me question what “enough” really means, and how fragile success can be if it isn’t designed with foresight. I learned to build systems that could bend without breaking, designing for volatility instead of assuming permanence.
Freedom, I’ve learned, is being able to let go, to release the things you don’t actually need, and to do so without regret. True freedom isn’t measured by how much you earn or how many toys you have. It’s measured by how little you depend on them to be happy.
It became a cornerstone of my own philosophy, drawn from Buddhism’s simple truth: that attachment is the root of suffering.
That realization changed everything for me. I stopped measuring success by accumulation and started measuring it by independence.
Fortunately, my partner – being Buddhist himself – shares those same values, and that shared mindset made everything easier. Together, we designed a life built around sustainability.
It wasn’t about living cheap. It was about living smart — building a lifestyle that never demands growth just to stay alive. That philosophy led me to question the larger illusion we all grew up with – what is often referred to as the American Dream.
The American Dream is Dead
Versions of this exist everywhere — in Canada, Europe, Asia — built on the same promise: go to school, get a job, build a career, buy a home, raise a family, and retire at 65. Contribute to your pension, trust that the system will take care of you, and someday you’ll have “made it.”
It promises stability, but in reality it creates dependency — on employers, on banks, and on a fragile idea of security that only works if nothing goes wrong. It trains people to build a lifestyle that fits their paycheque, not their purpose, and to spend forty years maintaining it. This is about socially-accepted servitude, it is not freedom at all. It’s slavery with a twist: but you can recognize it for what it is, follow a different path, and escape it.
I rejected the socially-accepted path early, when I started my first business. I didn’t want to wait until 65 to start living out my goals, or to rely on a pension to buy back my time. I wanted a life that didn’t depend on anyone’s system at all. Freedom, to me, meant building a system that supports the life I want, instead of trying to fit my life into someone else’s.
The promise of the dream worked in an entirely different era — when one income could buy a house, raise a family, and still leave room to save. But that world is gone. For most people today, wages have barely grown while the cost of living has soared. Houses now cost six to ten times the average household income in most major cities.
Secure defined benefit pensions have been replaced by riskier self-managed plans, and long-term job stability has faded into short-term contracts. People are told the same story — work hard, stay loyal, retire comfortably — but the math no longer supports it. It’s a lie.
The result is a quiet disillusionment: entire generations doing everything “right” and still falling behind. That’s why I call it a cultural myth, not because it was never true, but because it stopped being true long ago, and most of society never updated the story, clinging to that glorious ideal.
The world changed.
Adapting to Reality
Adaptation is key to survival. It’s evolution. Without it, even the best financial plan eventually collapses under new conditions.
I didn’t have a six-figure income. I had to make do with what I earned and learn how to stretch it strategically. That meant tempering reality — understanding my limitations and designing a plan that worked within them.
That’s the biggest mistake most people make: living beyond their means. As their income rises, their expenses rise with it. They never escape the loop.
I learned early on that change is necessary — especially when your resources are limited. You can’t keep doing the same things and expect a different outcome. That’s the definition of insanity. Change is the mechanism that makes progress possible.
Over the years, I’ve gone through the same kinds of major life events that shape everyone: moments of love and loss, health scares that shift priorities, financial hardship that tests patience, and those quiet, introspective phases of self-awareness that reveal who you’ve become. Each of these experiences leaves a mark, forcing you to adapt, realign, and decide what still matters.
What matters most is how you let these moments shape you, whether you resist them or use them as signals to adjust your path. To evolve, you have to know yourself well enough to recognize what truly drives you.
You have to understand who you are, why you are, what you want, and where you’re going.
Can you answer those questions honestly and feel their weight?
Does it hurt?
Does it make you cry?
I realized some time ago that my identity and self-worth had been built on what other people thought of me, that I was holding myself back, delaying the things I needed to do just to fit in with society. I was depressed, demotivated, clinging to a life I wasn’t sure about. The fear of facing the future and confronting uncertainty is what held me back. That discomfort was a signal, a message from my subconscious trying to tell me, trying to help me to move forward. It was time to ask myself those questions. Time to pivot in a new direction.
I no longer cared about being “weird” or not fitting in. If I couldn’t live authentically — if I had to become what others expected just to belong — how could I ever truly be myself?
I realized I didn’t need to follow a script. I didn’t need to do what everyone else was doing — get the job, buy the house, climb the ladder, retire at 65. Those were someone else’s expectations, not mine. I could write my own story, and build a life that actually reflected who I was, not what everyone else was.
Without that level of self-clarity, it’s easy to live reactively, to be pushed by circumstance rather than guided by intent.
That’s what I learned to do. Every experience — good or painful — became input. I learned to read those inputs and adjust the system to test desired outputs. Over time, that’s how I evolved the person I needed to become.
The Real Meaning of Retirement
Most people see retirement as an endpoint. A time to relax, play golf, travel, or sit on a beach with nothing to do. And that’s fine if it’s what they want.
But that was never my goal. My idea of retirement was an upgrade: a return to full creative mode.
When I ran my first company, I did a lot of writing and software development. I did it first for the joy and the experience of it, the creative satisfaction of building something from nothing. But I also had to make money from it. That meant compromises. I had to design software that would appeal to a broader audience, manage infrastructure within the confines of someone else’s budget, and constantly build a client base to sustain the business and my lifestyle. The creative process was always mixed with financial pressure.
Retirement, for me, meant going back to doing what I loved — writing, building, and developing — but this time for my own goals and personal achievements. To create because I want to, not because I have to.
All those years ago, I realized that if I could build a portfolio large enough to pay for my lifestyle, I could reach a point where I could do whatever I wanted without worrying about where the next paycheque came from. That became my guiding principle, not wealth for its own sake, but independence through design.
That vision required two things: time and autonomy. And that autonomy required money — not for status, but for stability.
To reach that, I had to spend years in the corporate world — using stability as leverage. My salary was predictable, and that predictability became the foundation for long-term planning. I divided my income between living expenses, debt reduction, and investment. Every month was a small trade: my time in exchange for the freedom I was building later.
The structure of a regular job gave me the consistency to design my own escape route. It wasn’t ever meant to be glamorous. It was strategic.
The Attainable Dream
Long before I ever thought about money or plans, I was driven by a different kind of imagination: the worlds I saw as a child through the stories and films that shaped me.
I grew up inspired by storytellers who imagined futures where humanity and technology worked together. They were not tools for power, but extensions of creativity, empathy, and curiosity. These stories weren’t just science fiction; they were philosophies of human potential — visions of what life could look like if we chose reason, compassion, and intelligence over fear and greed.
That vision never left me. It became the foundation beneath everything I built — from my fascination with software and design to my deeper interest in systems thinking and creative freedom.
In a sense, that’s what this entire journey has been about: designing a life that would allow me to help build that kind of world — one where technology doesn’t replace humanity, but expands it.
Becoming the Person You Need To Be
One thing I never could have expected was how much this process would change me.
At first, I wanted money for security. But over time, I realized I was actually building capability. Each stage — paying off debt, learning to invest, refining my habits — changed how I thought. I became more patient, more deliberate, more aware of how structure creates freedom.
By the time I reached my financial goal, I’d already become someone new — someone capable of living the life I had imagined.
Now, after two decades of personal growth and self-development, I’ve circled back to the creative life that started it all. Writing, software, filmmaking… all the things I used to dream about doing freely, I can now do without compromise.
This is creative sovereignty — the freedom to make and build what I want, how I want, without needing anyone’s approval.
I feel now like that’s what this whole journey was really about. Not comfort, not luxury, not an escape from work, but the ability to spend the rest of my life creating and contributing, in ways that feel honest and alive.
The Real Outcome
So what actually happened?
I followed a direction, not a perfect plan. I learned from every step, good or bad. I built systems that supported my goals. I worked within the system long enough to build independence from it.
The result looks like early retirement, but it’s really a creative beginning — a return to the dreams that started all of it.
Freedom doesn’t come from avoiding structure; it comes from building the right structure, one that serves the life you actually want to live.
Most people never start because of fear — fear of mistakes, fear of loss, fear that it’s too late. That’s the next piece in this series: how fear, properly understood, becomes a signal, not a stop sign.
From the series Financial Pragmatism in Practice — reflections on how deliberate structure and adaptive design can build a sustainable, independent future.