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The Rational Reminder Podcast

Shannon Lee Simmons: How To Stop Feeling Broke | #415

25 Jun 2026

Transcription

Transcript generated automatically by AI and may contain errors.

Chapter 1: Why do so many people feel financially broke despite good incomes?

4.216 - 16.096 Benjamin Felix

This is the Rational Reminder Podcast, a weekly reality check on sensible investing and financial decision-making from two Canadians. We're hosted by me, Benjamin Felix, Chief Investment Officer, and Cameron Passmore, Chief Executive Officer at PWL Capital.

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16.677 - 23.929 Dan Bortolotti

Welcome to episode 415. Ben, thanks for having me back. It's very nice to have you back, Cameron. It's been a while.

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Chapter 2: How does social comparison influence spending habits?

23.909 - 36.75 Dan Bortolotti

It's been a while and wow, what an episode to come back for. So this week we got a chance to have a conversation with Shannon Lee Simmons, who I'm sure many people have heard of. And boy, did she bring her game today.

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37.351 - 41.457 Benjamin Felix

She was incredible. I told her after the conversation that it's one of my favorite episodes.

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Chapter 3: What are the emotional impacts of cashless spending?

41.918 - 45.023 Benjamin Felix

Thinking back, it's one of my favorites. She was awesome.

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45.003 - 61.355 Dan Bortolotti

She's awesome. She's so articulate, but she's also like frontline working with people through situations. And she's done it for so long with such passion and enthusiasm. We threw lots of questions at her and some were off the cuff that she had not seen before. So it was great answers and great insights.

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Chapter 4: Why is traditional budgeting often ineffective?

61.796 - 66.285 Dan Bortolotti

But the insights are real. She's dealing with real issues with real people.

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Chapter 5: What is the four-bucket framework for worry-free spending?

66.265 - 70.852 Dan Bortolotti

at a volume and scale that you can tell she's gathered so many great insights over the years.

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71.913 - 85.894 Benjamin Felix

She's not just smart from experience working with people. She's like in a more abstract sense, very well informed about the advice that she's giving and about how markets work and all that kind of stuff. I think her advice is very aligned with the kind of stuff that we're telling people.

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86.262 - 104.17 Benjamin Felix

We did talk about, and this is something that's been popping off in the Rash Reminder community recently, we did talk about fee-only planning versus asset center management models for advice. Spicy topic. I thought she had really, really good comments on that topic. That's near the end of the episode that we talked about that.

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Chapter 6: How can couples navigate different financial priorities in retirement?

104.15 - 121.546 Benjamin Felix

She's written, I believe it's four books, three or four. She's written a bunch of books. She's thought a lot about this stuff, financial planning, financial decision-making, regret, all that kind of stuff. So that's mostly what we talked to her about. And some really interesting stuff is actually, we were on a panel together a while ago.

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Chapter 7: What common financial decision crises do people face?

122.246 - 140.004 Benjamin Felix

She, I guess, listens to Raph's reminder, but she said, a topic you guys have not covered is how household dynamics change in retirement. And she was like, nobody really talks about this. But she's seen it with many of the households that she deals with where couples are very much on the same page, pulling in the same direction.

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140.024 - 160.67 Benjamin Felix

They've got the same retirement goals and then they get to retirement. And once it comes to spending the money they've saved to fund their consumption while they're not working anymore, these differences that were not apparent while they were saving appear in how they want to manage the household's assets and how they want to manage their spending. That was her kind of initial pitch.

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160.69 - 163.697 Benjamin Felix

It was like, we should do an episode on this. So we did talk about that as well.

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Chapter 8: How can financial planners help clients overcome regret and anxiety?

163.737 - 181.271 Benjamin Felix

I thought that part of the conversation was really, really interesting, but it was very good, wide ranging conversation that I think people are going to like, but she brings an energy that's just, it was awesome. It was awesome for sure. Yeah, big fan. So she is a CFP professional. She's a speaker. She's a bestselling author.

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181.332 - 203.985 Benjamin Felix

She's also a chartered investment manager, and she's the founder of the New School of Finance. She is a fee-only financial planner. She's also a personal finance expert on CBC Radio's Metro Morning. She mentions it briefly as she worked in high net worth wealth management, I believe, prior to leaving to start her own fee-only financial planning firm.

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203.965 - 216.92 Benjamin Felix

So as I said earlier, she's very well informed, but also has this in the trenches practical experience working through real difficult emotional and financial planning topics with Canadians.

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217.761 - 221.366 Dan Bortolotti

I agree. Love it. Let's go to our conversation with Shannon Lee Simmons.

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226.752 - 229.015 Benjamin Felix

Shannon Lee Simmons, welcome to the Rational Reminder Podcast.

229.515 - 231.137 Shannon Lee Simmons

I'm so happy to be here. Thanks for having me.

231.573 - 234.916 Benjamin Felix

We are very excited to be talking to you. Why is everyone worried about money?

235.497 - 252.094 Shannon Lee Simmons

Well, I mean, besides the obvious that the cost of living has gone up and things are more expensive and all that kind of economic stuff, I think the big thing is that money is how we afford our lives. You want to go on a family vacation? That costs money. You want to go back to school and retrain? That costs money. You want to get married one day? You want to retire one day? Money, money, money.

252.254 - 261.023 Shannon Lee Simmons

So if you don't know whether that's all going to work out for yourself, then you're worried about it because you're worried about life not happening the way you want it to.

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