From debt to independence.
Almost eight years ago, I started working part-time in the financial services industry. Mostly this was to get insider knowledge of how the industry works, so I can learn how to better manage my own money, so I can better achieve my goals. I went to nearly every investment and retirement seminar I could, listening to fund managers explain their strategies, their mistakes, and what really worked. I absorbed everything I could from industry experts.
Along the way, I heard the same story from almost every client I’ve ever met. They sit down, tell me they want to retire early, and then they tell me why they can’t.
They say they have bills to pay, kids to support, or debt that never seems to shrink. Some say they aren’t investing enough, or they wouldn’t know what to do if they stopped working. Most are so focused on the day-to-day, the next meeting, the next project, the next big purchase. A new car, a bigger home, the latest phone.
And that’s the problem. We’re trained to plan for next week, not for the next version of ourselves. From the time we’re young, we’re told to follow a path that ends at 65 — it’s seen like some kind of magic number – work hard, save a little, and someday you’ll finally get to live. But that story keeps people trapped. They chase milestones that someone else defined — the promotion, the new car, the bigger house — and call it success. But that isn’t a life plan; it’s a countdown. When you’re locked into that kind of race, you never stop long enough to ask who you’re becoming, or whether the finish line you’re chasing is even yours.
Hearing their stories reminded me of my own, because I was once in the exact same position.
Two decades ago, I was a solo developer running a small software design business. I spent most of my days alone — coding, researching, avoiding people. It was safe, predictable, and deeply rewarding. I’ve always struggled with anxiety, and as an introvert, I was more at ease in my own head than in a crowd.
With the onset of the financial crisis in 2008, my business started winding down. I made a decision that, at the time, felt insane. I wanted to change not just my finances, but myself. So I stepped completely out of my element. I chose to work in hospitality, a world built on people, noise, and constant interaction. It was the opposite of everything I was used to. Then I went even further: I sold my Dodge Charger — which I loved — packed my life into a few boxes, and moved across the country to Vancouver.
No safety nets. No social network. No guarantees. Just me, an introverted tech guy, starting over in a new city and a new industry surrounded by people I didn’t understand. Looking back, that might’ve been the boldest decision I ever made up to now. It was terrifying, but it forced me to learn resilience, personal responsibility, and self-sufficiency.
And that’s really where Financial Pragmatism began — not as a system, but as survival. I learned that if I wanted freedom later, I had to start earning it through discomfort now.
I was $50,000 in debt at the time. But I had a vision of what I wanted my life to look like twenty years later. So I worked backward. I realized if I wanted that future, I needed a map, and a plan is exactly that: a map for your life.
So I figured out what I needed, set targets, and made small changes every day. I reviewed my spending, experimented with cutting what I didn’t need, and stayed focused on the plan.
Each decision, each small correction, brought me closer to where I wanted to be.
I told myself: fifteen years. If I could reach what I needed by then, I’d give myself permission to retire and go back to work on my creative endeavours.
Over the years, I would gorge myself with information, finding all the tools I’d need to arm myself with the knowledge to reach those goals. One book that changed my outlook was The Compound Effect by Darren Hardy. It taught me that big change comes from small, repeated actions. That became the cornerstone of Financial Pragmatism: the belief that freedom isn’t a miracle. It’s built through math, consistency, and patience.
But knowing the math wasn’t enough, I had to change how I behaved. Numbers are logical; people aren’t. I had to train myself to act consistently, even when emotion tried to pull me off track.
I learned to make it interesting. I gamified restraint. Each week I’d test myself: how many days could I go without buying something unnecessary? How much less could I spend than last month? Every time I resisted an impulse, it felt like a win. Instead of asking What can I buy? I started asking What can I go without?
That small shift changed everything. My savings grew, my stress dropped, and life got simpler. I started replacing overpriced brands with simpler, cheaper options that did the same job — and often, I realized I didn’t need the thing at all. Every “no” became a small victory — not just for my wallet, but for my peace of mind. I wasn’t depriving myself; I was teaching myself control.
Over the years, those quiet choices added up. I went from debt and little savings to financial freedom, not because I found the perfect stock or a lucky break, but because I built better habits. The math is important, but the mindset is everything.
That’s what I wish more people understood. Most people don’t fail because they don’t earn enough — though limited income can certainly be a factor. They fail because they don’t direct what they earn. Every raise comes with new expenses. Every bonus disappears into lifestyle upgrades. They plan for comfort, not freedom. The mindset I had to build for myself was the missing piece.
The path is simple: have a plan, have a goal, break it into small milestones. Save what you can — ten to thirty percent if possible — invest it wisely, and keep learning as you go. Those small, quiet decisions compound faster than you think.
Most people wait until it’s almost too late to start planning, but freedom only comes to those who plan before they need it.
The hardest part isn’t saving; it’s knowing when enough is enough. I struggled with that too. I kept thinking, “just a bit longer,” and a bit longer became a long time. Until I realized that the entire point of the plan was to reach this moment.
Now I’m here. The plan worked. I’ve reached the point I envisioned all those years ago. As I step into my 50s, the next few years are already mapped out — writing, film, creative projects, travel — all the things I once imagined doing someday.
And now, someday isn’t a dream anymore. It’s here.
I share all of this because I hope it reaches the people who can make the most of it. Especially if you’re in your 20s or 30s — this is for you. You still have time to design your life with intention, to build the habits that will buy you freedom later. Don’t wait until you feel ready. Start with what you have, where you are. The earlier you begin, the more forgiving time becomes. And if these words help even one person see that path a little more clearly, then sharing this was worth it.
I am proof of it.
Financial Pragmatism: The path to independence
This four-part series traces how I went from $50,000 in debt to retiring before 50 — not through luck, but through deliberate design. Financial Pragmatism is the system I built along the way: equal parts mindset, structure, and restraint. Each post explores a step in that journey — the trade-offs, the mental rewiring, the system that sustained it, and the freedom that followed.
Part 1: The Trade-Off
Part 2: The Mindset
Part 3: The System
Part 4: Freedom by Design