He revealed this on his popular The Wealthy Barber podcast on June 10, 2026, which you can find here. Later that month, Globe Advisor reporter Deanne Gage devoted a full column to his retirement (paywalled).
Chilton announced he plans to “shut down” at the end of 2026, including the now-two-year-old weekly podcast. But he will “continue to pump out our social media content” until early 2027. His main platforms are primarily visual media like YouTube, TikTok, Instagram, and Facebook, although he also has a presence on X, the former Twitter.
I interviewed Chilton for this Retired Money column early in August. He told me the podcast’s success was mainly generated by video shorts on Instagram and Facebook: “Some of these shorts will get half a million, 600,000 views. It’s crazy.”
A who’s who of Canadian personal finance
While the podcast does well on YouTube, the audio version gets more traffic on Spotify and Apple Music. In typical self-deprecating fashion, Chilton quips it’s because “people don’t want to see me.” Nor has his team attempted to monetize it: “We’ve never taken advertising money.” Initially the podcast was every second week, but it soon moved to weekly (on Tuesdays). So far, more than 70 episodes have aired, with perhaps another 20 scheduled before it shuts down. His guests are a who’s who of Canadian financial experts, but he has also interviewed a few Americans, including Motley Fool alumnus and author Morgan Housel.
Chilton makes a point of mentioning key members of his team: his assistant Mo (Maureen Ross), who has been with him 30 years, and Aidan Stride, the driving force behind the podcast.
Chilton fans have one more chance to see him on the speaking platform: he’s embarking this fall on one last major national media tour for private companies about “key lessons I’ve learned throughout my career.” There will also be a number of meet-and-greet book signings at Indigo stores.
Seeing as the Big Chill—as a mutual acquaintance calls him—is almost a decade younger than me, I must admit my initial reaction to his imminent retirement was one of surprise. After all, Chilton has been perhaps Canada’s preeminent personal finance guru ever since he published his pioneering financial novel, The Wealthy Barber, back in 1989. That book, which weaved financial advice into a story format, spawned several imitators, not least my own, similarly named The Wealthy Boomer.
Milking his one great idea
Chilton was 25 when he got the idea, wrote it up and published it at 27. The book launched Chilton on a successful four-decade career as an author and public speaker, with a stint in venture capital via the CBC’s Dragon’s Den. Between the various editions (U.S. and Canadian) and the subsequent The Wealthy Barber Returns, Chilton says total North American sales are between four million and five million.
Last year he released a completely rewritten Canadian edition of the original book, largely catering to the baby boomers’ children desperate to grab a spot on the first rung of the domestic housing ladder. That I can relate to as one of them is our daughter, now nearing 35. Project Flip, the audio version of the revised book, will continue indefinitely.
Clearly, Chilton is more than financially ready to retire but I didn’t press him on details. He’s divorced with two children and in a new relationship. We didn’t go into his own financial steps to implement his personal retirement. He’ll probably practise what he and his sources often preach and delay Canada Pension Plan (CPP) and Old Age Security (OAS) payments until 70. He doesn’t need to convert his registered retirement savings plan (RRSP) into a registered retirement income fund (RRIF) yet but he’s got plenty of time before calculating the optimum time to do so. In his video with retired actuary Fred Vettese, there is a discussion about annuities: Vettese usually says annuities may make up to 10% or 20% of total retirement income, but Chilton is reluctant to get pinned down on all-purpose recommendations on them: “Annuities in some instances should be looked at. Canadians for some reason, and often their financial advisors, don’t embrace them at all.”
One quip in the new edition is typically funny and made at his own expense. On the back cover is a blurb by Bob Chilton, Dave’s dad, who is now in his 90s: “Over 30 years ago, Marjorie and I told David, ‘You won’t be able to just keep milking your one and only good idea forever.’ Turns out we were wrong.” As David told Gage, “I only had one good idea in my life. I’m lucky I had it when I was young.”
Why retire now? Health, friends and family
One reason I was surprised by his looming retirement was that I had the impression Chilton really enjoyed the career the book spawned, something he confirmed both in his podcast and in the interview with Gage. When she asked Chilton how long he had been thinking of retiring, he replied, “It’s not something I’ve been thinking about at all,” as “I had instinctively felt I’d always work because I enjoy my work immensely.”
Why the change of heart? He cites two major reasons, one good and one bad. One is his growing realization that the health of friends and family can’t be taken for granted indefinitely, and by extension his own. As he said on a podcast episode entitled Dave’s Retirement he simply wants to spend more time with his friends while they’re still around and healthy.
This calls to mind a blog Fritz Gilbert published in The Retirement Manifesto, which I republished on my own site. On Your 12 Good Years, fellow blogger Dan Haylett estimated 12 years is “how long the average healthy 60-year-old has before their mobility, energy, and independence start to significantly decline. Not before they die… before life gets noticeably harder.” So if you want to travel and indulge in various sports and activities, you’d best start doing so before the 60–72 window closes forever. (As I have observed before, I personally am already outside that window.)
With 65 looming, Chilton is wisely making the move closer to the beginning of that optimal window for getting the most out of retirement. Soon after this column is published, his daughter will make him a grandparent for the first time, which is the “good” reason he mentioned.
Chilton says the data “is really getting quite robust supporting the fact that it’s 72. Not everybody, but the vast majority of people are going to start running into significant health issues.” That doesn’t mean they’re going to die then but he’s seeing health issues arise in many of his friends, several of whom are older than him. “That definitely played a role in my decision. I want to not only take advantage of the time myself, but I want to spend time with more of my friends and colleagues.”
