Should you act on these investing rules of thumb?

5i Staff May 06, 2026
Headline image for Should you act on these investing rules of thumb?

From 'The market climbs a wall of worry' to 'Sell in May and go away', here's how 5 investing axioms stand up

As most investors know, the market is filled with rules of thumb, colloquialisms and little snippets of advice designed to help you remember some rules and become a better investor. Let’s take a gut-check on some of these and see how they stand up in the current market environment.

The market climbs a wall of worry

We have all heard this one. It connects the equity premium that investors get for taking on risk in the market. Right now, we do not think it has ever been so accurate. There are so many things to worry about: multiple wars, inflation, valuation, presidential assassination attempts, oil, interest rates, earnings, AI-spending, AI-disruption and so on. You name it, and investors are probably worrying about it. Still, most markets hit more record highs again this week, as investors collectively said, “if there are so many worries right now, maybe there will be fewer in the future.” Optimists continue to make money.

You can never make 10,000 per cent if you sell after 100 per cent

Mathematically, of course, this is 100 per cent accurate. Selling a stock after a double seems great at the time but if you are going to sell the next Apple Inc., or Alphabet Inc., then maybe not. I will give you my real life (sad) example here: I was fortunate enough to buy Nvidia Corp. in 2016. It went up for a while and then soared. Of course, I practised prudent portfolio management and sold shares along the way. This week, though, the stock hit an all-time high. What does this mean for me? Well, it means that every single share I have ever sold was the wrong thing to do, at least from a profit-maximization point of view. Sure, maybe it was the right portfolio move, but it is still hard to watch it keep rising knowing how many shares I sold much lower down. Where does the market stand on this rule today? Well, we at 5i Research Inc. ran a recent Bloomberg screen and in North America found more than 1,900 stocks that have risen more than 100 per cent in the past year alone. Sure, some of these are tiny, risky small companies. But also more than 70 have market capitalizations of more than $50 billion. If you own one of these, maybe think twice about letting too much go.

Bulls and bears make money but pigs get slaughtered

This rule is always true. Greed has a way of wiping out portfolios. We are seeing some of this in the market today. Zero-day options still trade, leveraged exchange-traded funds (ETFs) remain very popular, the use of margin is at a record and prediction markets, which are essentially one-way bets, have exploded. Cryptocurrencies can get 40x leverage and risky investments in the quantum computing and other sectors are seeing their prices soar. There is not much we can say here: There will always be greedy investors and there will always be ways for people to lose lots of money, fast. Keep an eye on leverage and stick with quality. Remember, markets are high now, but drawdowns of 30 per cent and more are fairly common. Use caution. The market is not a lottery ticket.

A concentrated portfolio is the way to get rich

This is indeed true in theory but hard to enact in reality. Elon Musk, the richest person in the world, is the embodiment of this, as when Space Exploration Technologies Corp. (SpaceX) goes public he will likely have more than two-thirds of his entire US$1 trillion (expected) wealth tied up in just two companies. But such concentration is very hard for normal individual investors. Sure, Musk could lose a couple hundred billion dollars and still be able to feed his kids. For a Canadian saving for retirement, though, losing half of a $350,000 registered retirement savings plan (RRSP) account would be a devastating blow. Our suggestion for today’s market? Be reasonable. Six stocks are probably too few. But if you have 50 stocks your portfolio is going to be essentially an index, and that is not the way to get above-average returns.

Sell in May and go away

With markets at record highs it is surprising how little of this we have heard about this year. In prior years, it seems, it has been all the rage. But mathematically and historically, it just doesn’t work. Even before considering any commissions, bid-ask slippage or taxes, it just hasn’t proven to have worked at all. While it has been proven that markets do tend to rise more in the November to April period of the year than they do in the May to October period, the point is that they still (on average) rise. So, though you may make more money after November, you are still likely to leave money on the table if you exit the market in May.


 

Unlock the Power of Informed Investing with 5i Research! 

DIY investing doesn't have to mean going it alone. At 5i Research, we're your trusted partner in navigating the stock market. Our platform offers comprehensive stock and market research, empowering you to make smart investment decisions. 

  • Investor Q&A: Have burning questions? Get answers from our team of experts and fellow investors in our dedicated Q&A section.
  • Research Reports: With over 60 meticulously researched Canadian stocks, our reports offer in-depth analysis, giving you the confidence to invest wisely. 
  • Model Portfolios, Alerts, Forums, Portfolio Tracking, and Much More.


Take Care,

Peter's Signature


 

0 comments

Comments

Login to post a comment.

No comments have been posted yet.