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Resist the Urge to Make a Quick Profit on your Best Stock Picks

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Investors often go for the easy gains, but resist the urge to dump your best stock picks for a quick profit

Image courtesy TSInetwork.ca

Here’s a quote from one of the first highly successful investors I ever had the privilege of meeting. While talking about the stock market, he casually mentioned, “I’m a rich man today because I was smart enough to buy Canadian Tire stock at $0.50, and too stupid to sell when it hit $2.00.”

The quote deserves to be repeated more often, since it simplifies a key rule for successful investing and preserving your best stock picks: Don’t be too quick to sell a winner. Unfortunately, this rule gets broken all the time. Many investors buy a particular stock, often a junior stock, because they like a number of things about it: the business plan, the experience and achievements of the management, the outlook for the industry the company is targeting, the general economic environment, and so on. Before too long, however, other investors are likely to discover the same stock.

They may like it so much that they bid up its share price. When that happens, it can spur the early buyers to take profits.

These early buyers may lose interest because they fear the stock has burned up its near-term potential. Worse still, they may fear the rise is a “last gasp” and that the stock may suddenly go into a deep setback. Or, they may decide they found one good stock before the rest of the market did, so they can sell their latest winner and go on to invest the proceeds in something better.

Their initial good fortune may give them the urge to sell their first winner, in hopes of finding something else just as good, but with more profit potential because it has not yet caught the market’s attention.

Before you yield to this urge, it’s better to consider what else has changed about the stock, other than its rise in price. Did its business plan change? Probably not. Chances are that few if any of its attractive industry aspects have changed. Good management, good industry opportunities, a positive economic outlook and so on can persist through long periods of adversity.

That’s why you need to overcome the intermittent but all-too-human urge to take a quick profit on your best stock picks.

Mind you, before selling the stock and buying something else, you need to contemplate a related rule: Resist the urge to declare a junior investment a winner, just because of its novelty, or its uniqueness, or its frequent appearance in the broker/media limelight.

Lots of good-sounding investment ideas turn out to be poor investment performers.

Think long-term when it comes to maximizing gains on your best stock picks

The goal of an investor, particularly if you follow the Successful Investor approach, is to make an attractive return on your investments over a period of years or decades. Failure means making bad investments that leave you with meagre profits or losses.

Unsuccessful investors can still make some profits. They just don’t make enough to offset the inevitable losses and leave themselves with an attractive return. If you focus on the idea that you never go broke taking a profit, you may be tempted to sell your best investments whenever it seems the investment outlook is clouding over.

On occasion, you may succeed in selling just prior to a major downturn, and buying back at much lower prices. More often, prices will soon hit bottom and move up to new highs. If you buy back, you’ll pay higher prices. If you had followed this investment belief with Canadian bank stocks, for example, you could have missed out on some big gains over the years.

In hindsight, market downturns are easy to spot. Spotting them ahead of time is much harder, and impossible to do consistently. After all, if you could consistently spot market downturns ahead of time, you could acquire a large proportion of all the money in the world, and nobody ever does that.

The problem is that you’ll foresee a lot of market downturns that never occur. All too often, the market-downturn clouds disperse soon after skittish investors have sold. Good reasons to sell do crop up from time to time, of course, even if you follow a long-term conservative investing approach. But “You’ll never go broke taking a profit” is not one of them.

So, when is it the right time to sell your best stock picks?

Investors often ask, “When do I sell?” There is no simple, fits-on-a-t-shirt answer to the question. But there are some helpful guidelines. Continue Reading…

Avoid being trapped by a Mortgage as a FIRE Retiree: 5 Tips

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Can you really achieve Financial Independence when you still have a mortgage looming over you? Our insights will help you avoid feeling trapped by payments.

Image: Iryna for Adobe

By Dan Coconate

Special to Financial Independence Hub

Achieving Financial Independence early brings freedom, flexibility, and opportunities. But entering this new chapter requires thoughtful planning, especially when it comes to housing.

Avoid being trapped by a mortgage in early retirement by adopting a strategic approach that aligns with your financial goals. Whether you plan to downsize, relocate, or stay put, being proactive can preserve your hard-earned independence without a mortgage becoming a financial burden.

Below are five essential tips to guide you through managing your mortgage while protecting your financial independence.

Prioritize Paying off your Mortgage

Carrying a mortgage into Financial Independence can feel like dragging a heavy anchor. If you can, aim to own your home outright before retiring early. This eliminates one of the largest monthly expenses, giving you greater control over your budget. Many Canadians find success by accelerating their payments or making lump-sum contributions when possible. Debt-free living provides immense peace of mind and opens up new possibilities for pursuing the lifestyle you envisioned.

Consider Downsizing

Scaling down your home can offer financial and lifestyle benefits. Downsizing can free up home equity, reduce maintenance costs, and even lower property taxes. However, a well-thought-out plan ensures you don’t trade your current home for another financial burden.

It is possible to buy a new home before selling yours: you just need to be strategic about it. You also don’t have to limit yourself to smaller square footage; consider homes in less expensive areas or those better suited to your needs.

Explore Passive Income from Real Estate

Turning your property into a source of income can significantly offset costs. For instance, renting out a portion of your home or owning a rental property can transform your mortgage payment into a cash-flow opportunity. Many pursuing Financial Independence have increasingly tapped into short-term vacation rentals or long-term tenants to supplement their budgets. Proper research and planning ensure this approach aligns with your goals while providing notable financial advantages. Continue Reading…

Gold’s Shiny Moment — But I’m still not buying it

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By Alain Guillot
Special to Financial Independence Hub

It’s all over the news. The price of one ounce of gold is over $4,000

Millions of people — and even some governments — consider gold to be an investment. Good for them.

Ever since I became interested in investing, I’ve always dismissed the idea of owning gold. I still haven’t changed my mind, but I must admit: the gold bugs are having a good moment.

As of October 22nd, gold was trading at $4,067. That’s a 48% increase from one year ago when it was $2,744. Congratulations, gold bugs. Especially to my friend Michael who has been telling me to buy gold for the past 10 years.

It’s been an amazing run. If you had put your money into gold at the beginning of the millennium, in January 2000, you would have ended up with more money than if you had invested in the S&P 500. A lot more. About three times as much, as you can see from this chart.

And remember: the S&P 500 represents real businesses. Companies producing goods and services, generating profits, paying dividends, and giving you a claim on future cash flows — cash flows that are much larger today than 25 years ago. Gold, on the other hand, is — as British economist John Maynard Keynes put it — a barbarous relic. It produces nothing. It just looks shiny.

Yes, it has some industrial use in electronics, and millions of people all over the world wear it as jewelry. But economically speaking, it’s just a shiny object.

So how does this shiny object — which does nothing except sparkle — outperform one of the greatest bull markets in U.S. history? It boggles my mind.

Why I still prefer stocks

First, let me tell you why I prefer stocks.

The reason I prefer stocks over gold is simple: cash flow compounds.

When you own productive assets:

Companies earn profits.
They reinvest those profits to grow.
They pay dividends or buy back shares.
Your slice of the economic pie keeps expanding — even while you sleep.

That compounding effect is relentless. It’s like planting a tree that keeps bearing fruit year after year. Gold, on the other hand, just sits there. It doesn’t grow. It doesn’t reproduce. It doesn’t innovate. You’re entirely dependent on the next buyer being willing to pay more for it than you did.

That’s not investing. That’s speculation.

Why some like Gold

I admit it, gold does have a legitimate purpose:  it serves as insurance against currency collapse or geopolitical disasters. Imagine for a second that you live in a country with high inflation, like Venezuela. If you have gold, you don’t care that the local currency, the Bolivar, collapses. You are good, you have gold.

One possible reason for gold’s recent rise is central banks. Many of them have been buying gold as part of their foreign exchange reserves. Traditionally they buy U.S. dollars, but some of them are switching to gold because their relationship with the U.S. has been deteriorating. Continue Reading…

3 books I just read that Retirees DIYing their pensions need to read

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Amazon.ca

My latest MoneySense Retired Money column looks at a must-read new book on Retirement as well as two related books on DIY stock-investing. You can read the full column by clicking on the highlighted headline: Who you gonna trust: Barry Ritholtz or Jim Cramer?

The must read and main focus of the MoneySense column is William Bengen’s A Richer Retirement: Supercharging the 4% Rule to Spend More and Enjoy More. If that sounds familiar it should: Bengen’s original book on the 4% Rule is considered the bible of retirement, with his famous “SAFEMAX” guideline of 4% a year being an annual amount of withdrawals that should be “safe” for retirees to continue for a full 30 years, even after inflation. The original book,  titled Conserving Client Portfolios During Retirement, was first published in 2006.

Never mind that even Bengen considers 4.7% be a more universal SAFEMAX. The original book was aimed at financial advisors and professionals while the new one ostensibly is aimed at retail investors and retirees. I say ostensibly because I was a little disappointed with it and found the plethora of complicated charts and tables a bit much for lay investors. Still, there’s a lot of common sense there: Inflation is big long-term threat to retirees as are bear markets. Withdrawing too much from portfolios can be disastrous if you are unfortunate enough to retire just as a bear market hits and/or inflation starts to bite.

On the other hand, sticking with the old 4% rule or even the smaller amounts of 3% or even 2% advocated by some cautious souls, could result in you withdrawing less than you really need to enjoy retirement, although the tax department and any heirs might commend your caution and frugality.

How to make money in any market

Amazon.ca

While it’s rare for me to buy new hardcover books because I receive so many “free” review copies of financial books, I actually did buy A Richer Retirement as soon as it was available on Amazon. Plus, unusually, I also bought two other brand new books on the related topic of investing and stock-picking.

One was Jim Cramer’s How to make money in any market, by the sometimes revered but often maligned host of  CNBC shows Mad Money and Squawk on the Street. It’s fashionable for some financial journalists who believe in efficient markets and indexing to diss Cramer but I am not in that crowd. In fact, Cramer recommends that newcomers to investing put the first US$10,000 into an S&P500 index fund or ETF.

However, for seasoned investors and even retirees, Cramer suggests putting half a portfolio in index funds and the other half in individual stocks. Where we part company is his recommendation that the bucket of stocks be restricted to just five names, which would mean 10% in each. For my money, that’s way too concentrated and risky, even though he often brags about how he is often accosted by Nvidia Millionaires who tell him they bought that stock as soon as he announced on air that he had renamed his dog Nvidia.

How NOT to invest

Amazon.ca

Finally, regulars to this site may already have read Michael Wiener’s review of Barry Ritholtz’s How NOT to invest, which appeared here in this blog a few weeks after appearing on his Michael James on Money blog.

To be sure, those who are fond of disparaging Jim Cramer might quip that should have been the title of his own book, seeing as there are actually ETFs out there that try to profit by shorting Cramer’s picks. As of this writing, my copy has arrived but I have not yet finished reading it, as it’s a bit longer than the other two.

But based on the book blurbs and Michael’s review, I have no doubt it will be worth reading, whether for younger investors or seasoned ones and/or retirees.

Finally, while I only just received my review copy, I note that David Chilton is publishing a new edition of his classic financial novel, The Wealthy Barber, which any young person just starting to invest should acquire.  I look forward to revisiting it.

 

 

 

Adding DayMAX™ ETFs to Enhance Income and Diversification (HDIV/HYLD)

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Image courtesy Hamilton ETFs

By Hamilton ETFs

(Sponsor Blog: originally posted by Hamilton ETFs on Sept. 30, 2025)   

The Hamilton Enhanced Canadian Covered Call ETF (HDIV) and the Hamilton Enhanced U.S. Covered Call ETF (HYLD) portfolios have recently been modified slightly to introduce new positions in the DayMAX™ ETFs.

Over the years, portfolio changes within HDIV and HYLD have been made to meet their objective of providing attractive monthly income, while also considering improved diversification and other expected benefits for unitholders. In January 2024, HDIV and HYLD reached an important milestone with the full internalization of their holdings. This change removed all third-party ETFs, brought the top-level management fee of HDIV and HYLD down to 0% (subject to the fees of the underlying portfolio ETFs), and supported increases to monthly distributions.

Following the recent launch of the DayMAX™ ETFs, Canada’s first ETFs using zero-day-to-expiry (0DTE) options, a decision was made to introduce them to HDIV and HYLD, to help deliver higher yields and broader diversification.

DayMAX™ ETFs at a Glance

DayMAX™ ETFs are Canada’s first suite of ETFs to apply daily option strategies. By combining 0DTE options with modest 25% leverage, they aim to deliver higher and more frequent tax-efficient income. The lineup includes:

For a full overview, see DayMAX™ ETFs: Seize the Day.

Key Changes to HDIV and HYLD

The portfolio changes involved modestly reducing HDIV and HYLD’s exposure to select YIELD MAXIMIZER™ ETFs and adding positions in DayMAX™ ETFs, specifically CDAY, SDAY, and QDAY.

Both fund families are designed to generate high tax-efficient income, but they differ in how it is achieved. YIELD MAXIMIZER™ ETFs use longer-duration covered calls, while DayMAX™ ETFs employ Zero-Day-to-Expiration (0DTE) options, contracts that expire the same day they are written. This structure allows DayMAX™ ETFs to write options approximately 250 times per year, compared to 12 with traditional monthly contracts, creating more frequent opportunities to generate option premium income. By combining the longer-duration covered calls of YIELD MAXIMIZER™ ETFs with the daily options strategies of DayMAX™ ETFs, HDIV and HYLD are now diversified across time horizons and income streams, monetizing both monthly and daily volatility.

For the full list of updated holdings, please visit the fund pages: HDIV holdings and HYLD holdings.

Expected Benefits of Adding DayMAX™ ETFs to HDIV and HYLD

  1. Higher Yields: The introduction of DayMAX™ positions increases the internal portfolio yield of both HDIV and HYLD, supporting their primary objective of providing attractive monthly income.
  2. Increased Diversification: By adding DayMAX™ ETFs, HDIV and HYLD expand their holdings to broader exposure, increasing portfolio breadth.
  3. Improved Alignment to their Respective Markets: The sector weights of HDIV and HYLD are now closer to those of the Canadian and U.S. markets, respectively, as approximated by the sector weights of the S&P/TSX 60 and S&P 500. Continue Reading…