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My latest MoneySense Retired Money column looks at the imminent retirement of The Wealthy Barber himself: David Chilton. You can find the full column here: The Wealthy Barber retires.
Chilton, who will reach the traditional retirement age of 65 late this October, announced in June on his popular YouTube podcast that he’d be retiring at the end of 2026, a story soon picked up by the Globe & Mail.
My Retired Money column has focused on individual retirements now of Rob Carrick and blogger Mark Seed. Like Chilton, these people are younger than myself: I describe myself as only semi-retired, which is how I view Carrick and Seed. On his two-year-old The Wealthy Barber podcast, Chilton has now twice interviewed Carrick about his Retirement and also about his views on the high costs of housing.
As my MoneySense interview with him clarifies, Chilton views his transition as being closer to the traditional “Full Retirement” than the more gradual semi-retirement that Carrick and I are practicing. My view of Traditional Retirement is leaving a full-time salaried employee relationship and all that entails: commuting to a central place, bosses and meetings, taxes withheld at source, etc. Of course, Chilton has seldom if ever been an employee: he’s been a self-employed author and public speaker almost from the get-go. But as he reveals, his successful speaking career meant doing a lot of business travel and committing his time in advance: something he now wishes to reduce in order to have more personal freedom.
When and if he does pack it in in December, it will end an intense few years where he “aggressively” participated again in the Canadian personal finance content space that he helped pioneer in the first place.
Apart from public speaking, which he will cut back on in 2027, Chilton launched a successful biweekly podcast on YouTube that soon became weekly, promoted through video shorts on Facebook and TikTok. I can see how weekly podcasts could constitute almost a full-time job in itself so it should be no surprise that he will wind that up at the end of the year, despite the fact many around him would like to see it continue in some form.
Rewritten Canadian edition of The Wealthy Barber took longer to do than the original
The other big push he made was a massive two-year extensively rewritten 2025 Canadian edition of the book that made his career when he published it at age 27 in 1989. Chilton says it took him longer to revise (rewrite) the new edition than to write the original! His focus is on Canadians 45 years old or younger, many of whom are struggling to get a toehold in the housing market (which includes my own daughter).
His own daughter is one of the “good” reasons Chilton cites for ending his “public facing” career: he’s about to become a grandfather for the first time. Of course he still intends to do a bit of public speaking: maybe ten gigs a year, and while his YouTube podcast is slated to cease by the end of 2026, he may keep up some social media presence.
So far, the almost 100 weekly interviews he has conducted is a who’s who of Canadian and some American financial gurus, including Carrick, Fred Vettese, Morgan Housel, Ben Felix, Michael Wiener and many more. (Wiener is better known from the name of his blog, Michael James on Money. His review of Chilton’s new revised edition was also republished on Findependence Hub, here.). 
I’m scheduled to appear on the podcast myself in the next few weeks.
From where I sit, Chilton certainly seems to have the Midas Touch and I wish him well in his semi-busy “Full Retirement.” I have little doubt he’ll pull off writing the play he says he wants to write and ultimately staging it. (He tried writing a play in his youth, even before the book was conceived.) And when you think about it, The Wealthy Barber itself is not unlike a play, as it is primarily a series of dialogues between characters, often delivered with Chilton’s characteristic wit.
“It’s kind of the one thing on my bucket list, for whatever reason, I’ve always wanted to accomplish, is to write something and actually get it on stage somewhere. So I’ll make that a pretty quick focus when I retire in December. ”
I have no idea what the title might be but anyone who wants to help him brainstorm it are welcome to append suggestions in the comments section. The Wealthy Playwright, perhaps?
