How to Clean Up Your Dividend Portfolio (Without Panic or Regret)

Every investor’s portfolio ends up a bit like their garage.

You start with good intentions. You add new positions. Then, over time… it becomes a cluttered mess.

You’ve got duplicates, tiny holdings you forgot about, a few sentimental “losers,” and probably a couple of overgrown positions too.

Spring is the perfect time to declutter your portfolio—and I’ll show you how.

First: Why You Need to Clean It

Think of your portfolio like a garage full of tools. If you’ve got seven different types of salt in your spice rack—or five Canadian banks in your RRSP—chances are you’re not gaining extra protection. You’re just making your portfolio harder to manage.

A messy portfolio leads to:

• Missed red flags: It’s easy to overlook a dividend cut or weak quarterly result when you’re tracking 50+ positions.

• Confused strategy: Without alignment, your portfolio becomes a mash-up of old ideas, random tips, and “why did I buy that again?” stocks.

• Opportunity cost: Poor performers tie up capital that could be invested elsewhere, compounding returns.

• Analysis paralysis: Too many stocks, no clear rules = inaction.

Let’s fix that.

Step 1: Spot the Duplicates

Holding a bunch of stocks from the same sector doesn’t mean you’re diversified. In fact, it could make your portfolio more vulnerable.

Do you really need 4 railroads, 5 Canadian banks, and 3 life insurance companies?

Probably not.

How to choose the best one:

• Use the Dividend Triangle: Look at each stock’s revenue, earnings, and dividend growth over 5–10 years.

• Use comparison tools: At Dividend Stocks Rock, we use a stock comparison tool and dividend triangle charts to show clear winners and laggards in each sector.

• Example: Compare National Bank vs. Scotiabank—the numbers don’t lie. One quietly crushed the other for over a decade.

Step 2: Trim the Tiny Positions

Small positions (<2% of your portfolio) don’t move the needle, but they still add complexity.

Ask yourself:

“Do I believe in this company enough to build it into a full position (e.g. 3%)?”

If not, why keep it?

Tiny positions are like clutter in your garage—you’re not using them, and they’re taking up mental space. Sell, simplify, and reallocate that capital into something with real conviction.

Felling Lost in the Investing Process?

You’re not alone. Whether you’re sitting on cash or trying to fix a messy portfolio, it’s hard to know where to start—or what to do next.

That’s why we created the DSR Investment Roadmap.

This simple, step-by-step guide takes you from “What do I do with this money?” to “Boom! I’ve built a solid, diversified dividend portfolio.”

Ground rules, filters, stock selection, position sizing, mock portfolio setup—it’s all covered.

Grab the Investment Roadmap and take back control of your portfolio

Step 3: Rebuild Conviction

When was the last time you:

• Checked a company’s quarterly results?

• Reviewed your investment thesis?

• Ask yourself, “Would I still buy this today?”

It’s easy to coast on old research or assume “blue chip” equals bulletproof. But businesses and economic conditions change—so must your understanding.

Tip: Use quarterly summaries or stock cards to stay informed in minutes, not hours. DSR members can track 400+ companies with clear, up-to-date snapshots—no need to read every 30-page report.

Step 4: Know When to Sell a Loser

“If I don’t sell, I haven’t lost money.”
That logic keeps more investors stuck than anything else.

The real risk? Dead money.

Holding a loser for 5–10 years that never recovers ties up capital that could’ve been working for you elsewhere.

What to do:

• Revisit your investment thesis: Is it still valid?

• Look at the numbers: Are they improving or declining?

• Set a timeline: Give the company 1–2 years to turn things around, and monitor closely.

If nothing changes, take the loss, free up the capital, and move forward. That’s how you win long term.

Step 5: When to Sell a Winner

This one’s even tougher—because it feels wrong.

“But it’s up 150%! Why sell now?”

Because the price is rising, but the story may be falling apart. Maybe the dividend growth is slowing. Maybe earnings are declining while the market is still euphoric.

Example: I sold Texas Instruments and BlackRock after 100%+ gains. Why? Because the financial metrics no longer supported the high price.

When Do You Sell a Winner? – January Dividend Income Report

The same rule applies: If the investment thesis no longer checks out, sell, even at a profit.

Step 6: Cut What Doesn’t Fit

Sometimes, you’ve got holdings from:

• Old strategies

• Random “hot picks”

• Well-meaning friends

If a stock doesn’t align with your strategy today, it doesn’t belong.

“You can mimic someone’s portfolio, but not their conviction.”

Without a clear reason to own it, you’ll second-guess yourself when the market turns. Sell what doesn’t fit and focus on building a portfolio that matches your goals.

Step 7: Use Simple Rules

Let’s make this whole process easier with a few evergreen rules:

Asset Allocation Rules

• Fully protected assets (cash, GICs): e.g. 10–20%

• Partially protected (bonds, preferreds): e.g. 20–30%

• Not protected (equities): e.g. 50–70%

• U.S. vs Canadian split: Set a % range for each. Example: 50/50

This gives you a map, so when your U.S. stocks jump from 30% to 45%, you know it’s time to rebalance—without second-guessing.

The Vanguard investors quiz is a good method to help you figure out the right asset allocation.

Holdings & Position Size Rules

• Holdings: Aim for 20–40 to balance diversification and manageability.

• Target position size: Use this to guide new purchases and trim overgrown positions.

• Overweight limit: Decide your max exposure per stock. For example, if losing 50% of a $60,000 stock would make you queasy, cap each position at 6% of your portfolio.

Final Thought: Avoid Analysis Paralysis

“The deer in headlights” moment happens when investors face too much information—and no clear plan.

The solution is simple:

• Cut the noise.

• Stick to your strategy.

• Let the numbers tell the story.

• Make decisions based on facts, not feelings.

When you clean up your portfolio, you take back control. You reduce stress. You increase conviction. And best of all—you put your money where it matters most.

Ready to Build a Portfolio You Can Be Proud Of?

Cleaning your portfolio is just the start. If you want to build a strategy that lasts for decades, not just the next market swing, you need a plan.

The DSR Investment Roadmap gives you exactly that:

• A proven path from cash to confidence

• Clear steps for picking the right stocks

• Smart filters, mock portfolios, and rebalancing tips

• Built-in support for long-term dividend investors

Download your free copy now and take your next step as a confident investor.

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