Episode 365 – Rob Carrick's Eight Lessons Learned in 27 Years of Covering Personal Finance

In this episode, we welcome back Rob Carrick—one of Canada's most trusted personal finance journalists—for his third appearance on the Rational Reminder podcast. Rob recently retired after an incredible 27-year career at The Globe and Mail, where he shaped how millions of Canadians think about investing, advice, and their money habits. Rob joins Ben, Cameron, and Dan to reflect on the biggest lessons from his decades-long career, the state of Canadian financial advice today, and why young Canadians face headwinds unlike any previous generation. From the shift from mutual funds to ETFs and the rise of DIY investing to the dangers of overestimating stock returns and underestimating inflation's bite—Rob shares practical, timeless wisdom for every generation of investor. We also hear Rob's frank thoughts on how the financial industry fails seniors, why Canadians stick with the big banks despite better options, and what stay the course really means when markets inevitably crash again.

Key Points From This Episode:

(0:00:04) Rob Carrick returns for his third appearance, marking his retirement from The Globe and Mail

(0:06:39) Why it's harder than ever to be good with money in the social media age

(0:08:19) How longer lifespans are reshaping traditional retirement timelines

(0:09:51) The evolution of financial advice: from mutual fund sales to real planning

(0:11:45) How regulation, ETFs, and self-interest changed the advisory industry

(0:12:45) The rise of DIY investing in Canada: from brokers to discount online platforms
(0:14:51) Why some investors still struggle to embrace ETFs

(0:17:11) The flip side of frictionless DIY investing—when simplicity fuels speculation

(0:18:19) How realistic are today's stock return expectations?

(0:20:03) The true challenge isn't average returns—it's enduring the volatility

(0:24:01) Why staying the course should really mean buying the dip

(0:26:04) The generational reality check: how boomers bought homes and why today's young people can't

(0:29:03) How advisors can adjust advice for younger clients facing new headwinds

(0:31:39) Should 25-year-olds give up or go all in? Rob's advice for young investors

(0:35:29) The myth of home-run investing and why steady, boring investing works

(0:37:04) Why inflation has done more damage than any stock market crash

(0:39:50) How the financial industry ignores seniors—and what needs to change

(0:43:32) Canadians' blind loyalty to big banks and why you should try an alternative

(0:46:29) How Rob will define success in retirement—and his parting advice for listeners

Links From Today's Episode:

Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p

Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.

Rational Reminder Website — https://rationalreminder.ca/

Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/

Rational Reminder on X — https://x.com/RationalRemind

Rational Reminder on TikTok — www.tiktok.com/@rationalreminder

Rational Reminder on YouTube — https://www.youtube.com/channel/

Rational Reminder Email — info@rationalreminder.ca

Benjamin Felix — https://pwlcapital.com/our-team/

Benjamin on X — https://x.com/benjaminwfelix

Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/

Dan Bortolotti — https://pwlcapital.com/our-team/

Dan Bortolotti on LinkedIn — https://ca.linkedin.com/in/dan-bortolotti-8a482310

Cameron Passmore — https://pwlcapital.com/our-team/

Cameron on X — https://x.com/CameronPassmore

Cameron on LinkedIn — https://www.linkedin.com/in/cameronpassmore/

Episode 108: William Bernstein - https://rationalreminder.ca/podcast/108

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)