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!
Funny you are raising the topic of splurging in retirement with better airline seats for the second week in a row! I was tempted to comment last with with similar feedback … Sometimes, especially for time rich retirees, the splurge doesn’t have to be about the seat upgrade. For my husband and I, a direct flight, or a mid day short haul flight wins out every time. These are always worth the extra couple hundred dollars over the long travel days due to multiple connections and 3 am wake ups to catch that 6am flight.
Instead of spending the big bucks on business class seats for a few hours of comfort, we prioritize the dollars towards a more comfortable month long stay in an Airbnb.
Credit card travel rewards points are attractive to those who know how to use them, and do a deep dive on terms, conditions and associated fine print. Unfortunately, it’s the airlines and credit card companies who own the points and can arbitrarily change the value of them — or revoke them — as they please. Unaware points holders have no recourse: many people have their points cancelled without their knowledge because they didn’t read the fine print, or redeem them by a specified date. (I speak from experience on the latter.)
In particular, it’s worth noting that as of January 1 Aeroplan points redeemed on Air Canada flights are going to significantly change in value. Prince of Travel and Canadian Jetsetter do a good job of explaining how points holders are getting rooked. Accordingly, I no longer buy into Aeroplan promotions, or purchase top-up points. Why buy something that will be devalued in two months from now? This said, some cards are still worth the effort. The Amex Cobalt is a great card, and points are transferrable to a variety of carriers.
Knowing how to maximize value matters, too. Websites like Seats.Aero and Roame are invaluable for finding points deals. My wife and I recently scored Business Class tickets from Vancouver to Zurich and back for 70,000 points per person each way.
Regardless of what card or points plan people have, the motto of savvy points users is “Earn and Burn”. Banking points for years will only result in them shrinking in value, or even disappearing. In other words, use ’em or lose ’em!