I’ve long been a fan of rewards credit cards and the points-and-miles game. In 2019, we redeemed almost a million points for a 32-day trip to Scotland and Ireland – four Aeroplan flights and five nights at the Sheraton Edinburgh and the Westin Dublin, all ‘free’ thanks to Marriott Bonvoy.
Then came the ‘revenge travel’ year of 2022, when we flew business class to Rome in April, London in July and Paris in October. It all sounds incredible – and it was – but it was also a learning experience.
Our 2019 “milk run” flights (Calgary-Chicago-Edinburgh, arriving at 6:30 a.m.) were 17-hour marathons from the back of the plane. Even the business class redemptions had their shortcomings: a one-leg “mixed cabin” route so uncomfortable that a fellow passenger joked: “It’s like sitting on a park bench!”
Six years later, I’m overrated free about convenient. No more red eyes, no more connections, no more park bench flights. These days I’m happy to pay for comfort and direct routes – even better when a sale or points top-up makes it feel like a deal.
Related: The credit card combination you slept on
WestJet’s direct long-haul flights from Calgary have become my favorite, and while the rewards aren’t as rich as Aeroplan’s, the Gold status for two years isn’t bad either.
So how does this apply to you?
I’ve had clients who were concerned about redeeming points for travel, even when their financial plans show more than enough spending room. They have internalized the same habit I once had: chasing “value” so hard that they forgot to enjoy what they had already earned.
If your retirement plan says you’ll die with a $4 million estate and a $1.5 million TFSA, but you’re losing sleep on a $5,000 trip, it’s time for a mindset change. Book the flight. Upgrade your seat. Stay somewhere you will remember for a long time.
Because the goal isn’t to die with the most points or the largest account balance. It’s about transforming your wealth into meaningful experiences today and during your retirement.
This week’s summary:
Last weekend reading I shared what the perfect financial plan could look like.
Then I told you how to turn it up and actually enjoy spending in retirement.
Finally, I updated my annual post on how to crush your RRSP contributions next year by using the T1213 form.
Thanks to Lisa Jackson for including my advice in her latest article for Neo Financial on saving versus borrowing for major expenses.
Weekend reading:
Should you just buy stocks until you die? Wall Street Journal columnist Jason Zweig looks at Scott Cederburg’s updated research on the optimal portfolio (100% global equities).
A fascinating one look at the global market portfoliowhich still consists of 49% of global equities, despite the rise of gold, crypto and private equity.
An important and timely piece by Preet Banerjee on how the The rapid rise of sports gambling is dangerous for our financial well-being (and social health).
Speaking of danger to your financial well-being, Ben Felix makes another secret call to address the ‘serious mistakes’ investors are making about these products:
Remember April 8, 2025? Markets were reeling from the tariff announcements and the S&P fell 15%. Taking a look at this week, we see that the S&P is up almost 18% this year, while international markets are up 29% this year and emerging markets are up almost 35%. Ben Carlson says so Staying the course worked again. I agree.
Hope gives life, but outperformance is rare. Exploring the stock market myth.
Figuring out where you fall on the maximiser/satisficer continuum can save you some time and money. Christine Benz creates the case for the good enough wallet.
“Before you go down the maximization rabbit hole, take a step back and ask yourself: Am I cut out for this? Do I enjoy spending time this way? Or will ‘good enough’ decisions produce a similar outcome with much less time and effort?”
America hasn’t had a ‘real’ recession since 2009. Ben Carlson muses on this again what happens in the next recession.
Please don’t do this: What happens if you selling real estate to a relative for a dollar?
Finally, here’s a wild look at how the Toronto’s condo bubble burst.
Have a nice weekend, everyone!
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