10 Money Rules I’m Teaching My Kids (and Still Live By Myself)

Practical lessons on debt, housing, investing, and mindset that actually hold up

Intro: Why This Matters
I’ve been on this private investor path for a long time. Yes, I’ve been full-time since 2018, but it was a side hustle and passion for over a decade before that. While this Substack leans toward public markets, the biggest driver of my success hasn’t been portfolio performance — it’s been my personal finance mindset.

Even if my returns were only average, I still could have left work by 45 (maybe sooner). As my oldest son gets more exposure to money, I’ve been thinking more about what values I want to pass down.

I touched on this in an earlier post about financial education, but this time I want to lay out some core money values I’m trying to instill in my kids. Some might surprise you. You can check out that post below.

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The Family Template
The money template we inherit from our parents is powerful. Without realizing it, we absorb their attitudes — not just the rules they state, but the habits we watch. Breaking free from those patterns takes real effort.

I think about this all the time as a parent. What am I teaching my kids intentionally, and what am I teaching them by accident?

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Rule #1: Be Honest, Accountable, and Realistic
As with most things in life, success starts with being real with yourself. High but realistic expectations beat having none — or setting goals that are impossible to reach.

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Rule #2: Don’t Borrow for Depreciating Assets
For 99% of people, the only debt worth taking on is for a home. Cars, boats, Pokémon cards, computers — they should all be paid in cash.

The biggest point of contention is cars. Many people say they need a new car to get or keep a job. But the truth is, there’s nothing wrong with an older car. If you can only save $10k for a car, then you’re buying a $10k car. The discipline of working within that budget — and researching hard — matters more than Bluetooth or A/C.

Sure, you’ll hear stories of someone who sold their car for more than they bought it. But those are exceptions, not reasons to justify debt.

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Rule #3: Renting Is Fine. Buying Is Fine. Just Run the Numbers.
Culturally, Canadians see renting as “less than,” but it’s not. With discipline, investing the difference can leave you well ahead.

If you do buy, your first home should be a true starter home. There’s nothing wrong with an older house that needs sweat equity. In fact, learning the costs and quirks of homeownership is part of the education.

And remember: unless you’re flipping or renting properties, your home is not an investment. It’s where you live.

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Rule #4: Credit Cards Are Fine. Carrying a Balance Is Not.
Credit cards are the ultimate test of discipline. Even free cards offer great perks, but the interest rates are brutal. Pay them in full every month.

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Rule #5: You Don’t Have to Join the FIRE Movement
I’ve benefited from the FIRE mindset, but you don’t have to retire early to live a good life. Many people are perfectly happy working well into traditional retirement years.

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Rule #6: There’s No “Falling Behind”
A friend once told me he went back to school because he felt he was “falling behind.” When I asked if he liked the courses or had calculated the payback, he had no answer.

The truth is, you’re not on anyone else’s timeline. You can’t change the past, but you can change today and tomorrow.

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Rule #7: Don’t Live at the Extremes
Financial discipline doesn’t mean never enjoying life. No, you don’t need five pairs of Jordans — but a pair you really love, if it fits your budget, is perfectly fine.

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Rule #8: Automate the Important Things
Save, invest, and pay bills automatically. Prioritize what matters first, and make the rest a choice. The fewer money decisions you need to make each month, the better.

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Rule #9: You’re Not a Special Snowflake
There are no shortcuts. Sure, some people get lucky with options or crypto. But for every story of someone who nailed the timing, there are countless others who blew up.

Do what works. Stick with it long enough. That’s how results happen.

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Rule #10: You Don’t Need a Side Hustle
The internet loves to glamorize side hustles — flipping sneakers, driving Uber, drop-shipping. But for most people, the biggest wins don’t come from squeezing out a few extra bucks in evenings and weekends. They come from managing the money you already earn with discipline.

If you spend intentionally, avoid bad debt, and automate saving and investing, you don’t need three jobs to get ahead. A side hustle can be fun or fulfilling, but it shouldn’t be a crutch for poor financial habits.

After all, if you are fortunate you can always execute the original side hustle - work overtime.

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Closing Thoughts
That’s my list — or at least what comes to mind today. What about you? What personal finance rules do you live by? Drop them in the comments — I’d love to hear them.

Thanks for reading,
Dean