Weekend Reading: Points, Planes, and Permission to Spend Edition

I’ve long been a fan of rewards credit cards and the points-and-miles game. In 2019, we redeemed nearly a million points for a 32-day trip to Scotland and Ireland – Aeroplan flights for four, and five-night stays at the Sheraton Edinburgh and the Westin Dublin, all “free” thanks to Marriott Bonvoy.

Then came the 2022 “revenge travel” year, 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 misses: a “mixed cabin” itinerary with one leg so uncomfortable that a fellow passenger quipped, “It’s like sitting on a park bench!”

Six years later, I’m over valuing free over convenient. No more red-eyes, no more connections, no more park-bench flights. These days, I’ll happily 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 combo you’ve been sleeping on

WestJet’s long-haul direct flights out of Calgary have become my go-to, and while the rewards aren’t as rich as Aeroplan, Gold status for two years isn’t bad either.

So how does this apply to you?

I’ve had clients agonize over redeeming points for travel, even when their financial plans show more than enough capacity to spend. They’ve internalized the same habit I once had: chasing “value” so hard that they forgot to enjoy what they’d 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 over a $5,000 trip – it’s time for a mindset shift. Book the flight. Upgrade your seat. Stay somewhere you’ll remember.

Because the goal isn’t to die with the most points or the biggest account balance. It’s to turn your wealth into meaningful experiences today and throughout retirement.

This Week’s Recap:

Last weekend reading I shared what the perfect financial plan might look like.

Then I told you how to turn up the dial and actually enjoy spending money 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 a large expense.

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 stocks).

A fascinating look at the global market portfolio, which is still comprised of 49% global stocks, despite the rise of gold, crypto, and private equity.

An important and timely piece by Preet Banerjee on how the rapid rise of sports gambling is dangerous to our financial well-being (and societal health).

Speaking of danger to your financial well-being, Ben Felix is taking on covered calls once again to address “serious errors” that investors are making about these products:

Remember April 8th, 2025? Markets were reeling from the tariff announcements and the S&P was down 15%. Fast-forward to this week and the S&P is up nearly 18% on the year while international markets are up 29% and emerging markets are up nearly 35% year-to-date. Ben Carlson says that staying the course worked again. I agree.

Hope springs eternal, but outperformance is rare. Exploring the myth of the stock picker’s market.

Figuring out where you land on the maximizer/satisficer continuum could save you some time and money. Christine Benz makes the case for the good enough portfolio.

“Before you go down the maximizer 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 achieve a similar result with much less time and hassle?”

America hasn’t had a “real” recession since 2009. Here’s Ben Carlson once again musing on what happens in the next recession.

Please don’t do this: What happens if you sell real estate to a family member for a dollar?

Finally, here’s a wild look at how the Toronto condo bubble burst.

Have a great weekend, everyone!