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In my last article, I introduced the Health Spending Account (HSA) as a unique and simple tool for corporations of 1-through-10,001-and greater employees to either augment or define the foundation of their health benefits plan, using tax-preferred funds. In this issue, we’ll dive deeper into unique planning strategies for business owners to help identify the most efficient plan structure to suit their needs.

Over the years, several people have offered their thoughts about tax refunds and what to do when we get them. The first thing that most commentators point out is that a refund is a de facto admission that you have overpaid through tax withholdings and/or instalments over the previous tax year. Calibrating the amounts you’ll need to remit regularly and then paying accordingly helps. It is important to incorporate not only your income level, but also the deductions you are likely to incur along the way.

I was outside watering my garden when I saw Sandra come by. She’s my neighbour—friendly, always ready to lend a hand, and someone I enjoy talking with.

We smiled and started chatting, just like usual.

Knowing that I talk to families about estate and legacy planning, it made it comfortable for her to start talking about her family.

With the year winding down, savvy Canadian investors start thinking about tax loss selling to optimize planning opportunities and reduce tax. Tax loss selling is a planning strategy that allows investors to offset taxable capital gains by realizing capital losses in their portfolios. While relatively straightforward, the rules around tax loss selling—particularly the deadlines, superficial loss rules, and integration with broader financial goals—are nuanced.

Incorporated business owners can choose how to pay themselves. Some receive limited input from their accountant regarding their compensation strategy, or they simply continue using the same approach without occasionally reconsidering it.

With the rise of social media and influencers sharing all kinds of information, it’s not always easy to know what to believe. This is also true with financial influencers or “finfluencers” who offer financial advice to their audiences. What’s important to remember is that you can’t always trust what you see or hear on social media. And with an increasingly complex financial landscape, it can be daunting to know how to choose financial products and services that are right for you.

2025 has been another solid year for the overall U.S. stock market. As of September, both the S&P 500 (SPY) and Nasdaq 100 (QQQ) have delivered strong total returns, providing investors with year-to-date gains of around 13% and 17%, respectively. This marks the third consecutive year of double-digit returns.

Most financial advice is geared to middle- and upper-income Canadians. Ironically, the low-income earners most in need of financial advice feel they can’t afford it, while fee-based advisors have little incentive to seek out those with tiny accounts.

A research report led by Securian Canada from October 2024 revealed that more than one in five Canadians, or about 7.3 million adults in Canada, participate in the gig economy. Further, the study revealed that almost three-quarters of them do gig work as a “side-hustle”, meaning they are also employed full-time or part-time.