You can’t have everything. But you can have control.
An introduction to Financial Pragmatism
I retired before 50. Not because I won the lottery or built a unicorn company, but because I made deliberate, sometimes uncomfortable choices. I sold my Dodge Charger and started using transit. I stopped eating out and learned how to cook. I reviewed my spending and cut out anything that wasn’t essential. I cancelled cable TV and just watched YouTube and Netflix. I downsized services to fit my actual needs, not my imagined ones. I even stopped buying junk food and alcohol.
Over time, my expenses slimmed down. My debt disappeared. My savings grew. I didn’t aim for a glamorous life; I decided to live an intentional one. Every decision was made consciously, with my future self in mind.
This didn’t happen overnight. It started from a plan I made with myself twenty years ago, when I was deep in $50,000 of debt, had no investments, and winding down my first business. That moment forced me to think long-term: What if I could retire by 50? How much money would I need to never have to work again? It wasn’t philosophy — it was math. Once you find the answer, you work backward.
When I said I built a plan, I meant it literally — a map. I started with the destination and worked backward. If my goal was financial freedom by 50, then I needed to know exactly how to get there, step by step. I treated it like an engineering problem: what rate of return, what savings rate, what time horizon.
I casually studied long-term market data. Historically, the S&P 500 had averaged around 10 percent annually over a hundred years. Of course, it wasn’t steady — there were ups and downs — but over time, the trajectory was upward. I figured if I could capture a piece of that and stay invested through every cycle, the compounding alone would do most of the heavy lifting.
When I began, the market was still flat after the dot-com collapse — a quiet decade of single-digit growth. It didn’t look very exciting, and I had hesitation to put all my money into this idea of investing. Before this, I only knew building businesses, but even that turned out not to always be a sure thing. I diversified early: a mix of U.S. equities, Canadian markets, and a handful of sector funds in technology, value, small cap, and financials. My goal wasn’t to beat the market, but to ride it intelligently — wide exposure, minimal reaction.
A friend of mine was a licensed financial advisor and gently guided me at first, giving me a foundation of financial education and confidence to get started. Most people stop there. After a few years, I decided to take the training wheels off and go about doing it on my own.
Within a few years, those slow years turned into strong double-digit gains. The timing helped, but it was discipline that kept me from chasing trends or abandoning the plan. I learned quickly that markets move in rotations — leadership changes, cycles shift, and what wins one year often loses the next. I’d seen too many people over-concentrate and pay the price. So I kept my allocation broad and consistent. When one side fell, another side softened the landing.
That’s what a financial map really is: a structure that can survive your own emotions. A guide that lets you keep going when instinct tells you to stop. It’s not about finding the perfect investment, it’s all about designing a path that works even when things go wrong.
Most people don’t realize how early they need to start. The biggest mistake I’ve seen — as both an investor and advisor — is waiting until it feels urgent. People spend their 20s and 30s thinking they’ll plan later — life gets in the way — and by the time they finally start, the compounding window has already closed halfway. Time is the one asset you can’t buy back. Start early, start small, but start.
So I built my life around that equation. I limited my spending, tracked every dollar, and kept the focus simple: spend less than I earn. Managing finances, I realized, is much like managing weight. Calories in, calories out. If you consume more than you burn, you gain weight. If you spend more than you earn, you lose wealth. It’s math.
But over time, I learned that it isn’t just math. Numbers can give you structure, but they can’t give you discipline. To stay consistent for decades, you need a mindset — one that can delay gratification and stay focused when comfort calls your name. You need to train your behaviour, build habits that hold under pressure, and keep your goals visible when life tries to pull you off course.
Not having a map means you’ll never reach your destination. I spent the next two decades refining mine — defining my goals, setting milestones, and learning everything I could. I learned how to invest properly, how to evaluate progress without emotion, and how to make the most of every dollar I earned. Each step was part of a larger system — one that turned discipline into freedom.
That’s the heart of Financial Pragmatism. You don’t need to be a genius to retire early. You just need structure, self-awareness, and a plan you’ll actually follow.
In the rest of the series, I’ll explain how that system works — the one I built and still use today — to keep money flowing where it matters most.
Continue to part 2 – developing the mindset.
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