This article first appeared in the Globe and mail
on January 30, 2026. It is republished with permission.
January is a great time to sharpen your behavioral game. Your investing routine, along with periodic actions and reactions, are key factors in your investment results. They are even more important than choosing a good stock or fund, or keeping costs low.
At a time when there are so many unanswered, or should I say, unanswerable questions about AI, cryptocurrencies, trading and geopolitics, I have five questions that are eminently answerable. They aren’t necessarily easy, but if you tackle them honestly you will improve your returns in the long term.
Does my strategy match my skills, experience and available time?
It has never been easier or cheaper to be a DIY investor. You can access great information on the internet and trade stocks on your phone in seconds. But does going alone suit your situation?
You need to make sure you have time to dedicate to the process, week after week, month after month, and year after year. The more periods you are unable to attend (travel, family, work), the less of your portfolio you have to manage yourself.
And then there are skills and experience. You need to have a good sense of valuation, the most reliable predictor of future returns and portfolio construction. It also helps if you’ve been through a few cycles and seen different types of markets.
If you don’t have good answers to these questions, keep your trading account small and take the time to test your approach over a full market cycle.
What is the purpose and time frame for the money?
This is the basis for every investment decision. Together, these two things determine what risk is for you.
If your time frame is short, the risk is stock market volatility. The priority is safety and limited downside. If your investment horizon extends over decades, stable short-term returns are unimportant. Your biggest risk is not having enough exposure to assets that will grow. In other words: not taking enough risks.
Can I maintain my current risk level in all types of markets?
It’s one thing to have a portfolio that suits your goals, but theory can be very different from reality. Can you stick to your strategy in noisy market conditions where emotions run high? It is best to assess your endurance in advance, because your investment mix is only suitable if it can be sustained.
Look in the mirror and ask how you felt before when your portfolio fell in value. What actions did you take during the 2008 financial crisis, during COVID-19 and on Donald Trump’s Liberation Day? Did you stick to your plan in 2025, when FOMO was rampant? And have you taken advantage of weak periods by rebalancing your portfolio?
If you abandon your plan and retreat (or go all in after being too conservative), chances are it’s for emotional reasons and at the wrong time.
Do my advisor and I know enough about each other?
When you put your financial future in someone else’s hands, you need to know a lot about that person, and vice versa. I am not talking about sensitive issues, but about basic matters that go beyond your objectives. Your investing personality, communication preferences and what’s important in life.
Is your advisor or portfolio manager willing to answer all your questions without reservation? After telling you about the winners, do they also discuss the losers? And do they talk openly about your long-term results and the costs you pay?
If you’re not there yet with this person who will shape your retirement, fix it. Spend more time together. Make it clear how you want to be communicated and at what level. Remember, there is only one boss. You.
Who can I trust to tell me what the stock market will do?
Regular readers will immediately know that this is a trick question. If you base your strategy on what the market will do next month, you need to work on your behavioral game. Timing the market is one of those unanswerable questions.
#questions #investor