Building Your Investing Rules: Never Let Your Investment Fail You
Investing without rules is like sailing without a compass. You may drift along while the sun is shining, but the moment the seas get rough, you’ll find yourself lost, scrambling to make decisions based on fear or impulse. That’s how portfolios fail.
The antidote? Building your own set of investing rules — a framework that protects you from costly mistakes and keeps you on course toward your financial goals.
I like to think of these rules in two parts: Principles (the foundation) and Guidelines (the playbook you put into practice). Together, they become your personal investment system — one that ensures your portfolio will serve you in good and bad times.
Principles: Your Investing Foundation
These are the timeless beliefs that should anchor your decisions. They won’t change with market cycles, headlines, or fads.
1. Start with a Roadmap
Why: Without clear goals, time horizon, and risk tolerance, you’re investing blindly. Your strategy should align with your purpose — retirement income, wealth growth, or financial independence.
Example: A 30-year-old saving for retirement can load up on equities and ride out volatility, while a 65-year-old needing income must prioritize stability and cash flow.
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2. Diversify with Purpose
Why: Diversification protects you from being wrong. Canada’s market is concentrated in banks, energy, and materials — leaving investors exposed if those sectors falter. Global diversification balances risk and opens growth opportunities.
Example: Between 2014–2016, oil prices collapsed. Energy-heavy Canadian portfolios suffered, but investors with U.S. tech or healthcare exposure saw far less impact.
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3. Focus on Quality
Why: Strong businesses endure; weak ones don’t. Prioritizing durable business models, strong balance sheets, and consistent dividend growth reduces the chance of permanent capital loss.
Example: During the 2008 financial crisis, high-quality dividend growers like Johnson & Johnson maintained payouts, while speculative banks and leveraged firms cut dividends or collapsed.
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4. Stay the Course
Why: Emotional decisions ruin returns. Panic selling in bear markets locks in losses; chasing hot stocks in bull markets often means buying high. Staying the course ensures you capture long-term growth.
Example: In March 2020, the TSX dropped ~30%. Investors who held steady saw a full recovery within months, while those who sold missed the rebound.
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5. Harness the Power of Compounding
Why: Compounding is the engine of wealth. Reinvested dividends and long-term growth create exponential results over decades.
Example: $10,000 invested at 8% grows to $100,000 in 30 years. Without reinvestment, growth is much slower — you’re relying on savings, not exponential compounding.
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6. Keep Learning
Why: Markets evolve, businesses change, and tax rules shift. Stagnant investors risk being left behind. Ongoing learning sharpens your strategy and keeps your portfolio relevant.
Example: Investors who ignored tech in the 2000s missed the rise of Apple, Microsoft, and Amazon. Those who stayed curious and adapted gained exposure to some of the century's biggest compounders.
Guidelines: Your Investing Playbook in Action
Principles set the foundation, but Guidelines turn belief into action. These are practical boundaries and habits that keep you on track.
Portfolio Guidelines
- Limit any single sector to ~30% of your portfolio. 
 Why: Concentration magnifies risk, but within a sector (e.g., Canadian banks vs. insurers, or energy producers vs. pipelines), business models can still vary significantly. A 30% cap provides balance without being overly restrictive.
 Example: Within Canadian financials, TD, Sun Life, and Brookfield all operate in different niches. A 30% sector cap lets you own them all without overexposure.
- Maintain a margin of safety (cash buffer, avoid overleverage). 
 Why: Unexpected events happen. A buffer keeps you from selling investments at the worst time.
 Example: Investors with emergency funds in 2020 avoided selling stocks to cover expenses during lockdown job losses.
- Review your portfolio once or twice a year, not daily. 
 Why: Frequent monitoring leads to emotional decisions and short-term thinking.
 Example: Investors checking portfolios daily in March 2020 often sold in fear, while those reviewing annually stayed the course and recovered.
Business Guidelines
- Never invest in a company you don’t understand. 
 Why: If you can’t explain how it makes money, you can’t judge its future. Investing is about capturing, as best as possible, where the company is going and not where it has been.
 Example: Many bought into Nortel in the early 2000s without understanding its business — and lost everything when it collapsed.
- Avoid unsustainable payout ratios (over ~70%) or high debt. 
 Why: High payout ratios and debt reduce flexibility and risk dividend cuts.
 Example: In 2015, many oil companies slashed dividends when oil fell — payout ratios were unsustainable.
- Don’t chase yield — focus on dividend safety and growth. 
 Why: Very high yields are usually warning signs, not gifts. Active income investing with covered call ETFs is a different type of investing.
 Example: Investors chasing 12% yields in risky income trusts often faced dividend cuts and capital losses.
- Sell if dividends are cut or fundamentals break down. 
 Why: A cut signals management sees trouble ahead. Don’t wait for worse news.
 Example: When GE cut its dividend in 2018, the stock dropped further as fundamentals unraveled.
Process Guidelines
- Define your entry: fair valuation, yield, growth prospects. 
 Why: Buying with discipline avoids overpaying or chasing hype.
 Example: Investors who bought Canadian banks at depressed valuations in 2009 enjoyed outsized gains and dividend growth.
- Never sell just because a stock price drops. 
 Why: Price is not the business. Selling on fear often means realizing losses unnecessarily.
 Example: Apple dropped nearly 40% in 2012. Those who sold missed its multi-trillion-dollar growth since.
- Rebalance periodically, not reactively. 
 Why: Systematic rebalancing restores balance without emotional timing.
 Example: An annual rebalance in 2021 helped investors capture tech gains and shift into undervalued sectors, without panic-trading during volatility.
Tax & Cost Guidelines
- Keep fees low. 
 Why: Costs are certain, returns are not. Compounding fees erode wealth over decades.
 Example: If you start with $250,000 and earn 8% before fees, a 2% MER leaves you with about $1.44M after 30 years. Switching to a low-cost 0.1% MER boosts that to about $2.45M — more than $1 million extra just by reducing fees.
- Use registered accounts (TFSA, RRSP, FHSA) strategically. 
 Why: Taxes can take more from your returns than market volatility. Smart account use maximizes after-tax wealth.
 Example: Holding Canadian dividend stocks in a TFSA makes all income and growth tax-free — forever.
- Hold U.S. dividend payers in an RRSP. 
 Why: This avoids the 15% withholding tax under the Canada-U.S. tax treaty.
 Example: A U.S. stock paying 3% yields you 3% in an RRSP, but only ~2.55% in a TFSA after withholding.
- Keep Canadian dividend stocks in taxable accounts. 
 Why: They qualify for the dividend tax credit, making them more efficient than U.S. dividends outside registered accounts.
 Example: A $5,000 Canadian dividend could be taxed at a much lower rate than foreign dividends in a non-registered account.
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Final Thoughts
Your Principles explain why you invest the way you do.
Your Guidelines keep you disciplined with practical, real-world boundaries.
Together, they form a system that ensures your portfolio never fails you — no matter what the markets throw your way.
The sooner you write down your rules and commit to them, the sooner you’ll invest with clarity, discipline, and confidence.

