Q&A: Shannon Lee Simmons on Worry-Free Money and Making Financial Lemonade

Jane Switzer
by Jane Switzer March 29, 2018 / 1 Comment

Shannon Lee Simmons’ office is basically a confessional. After thousands of conservations with clients over the last decade, the Toronto-based certified financial planner and founder of The New School of Finance found a commonality: Everyone, no matter their income, is worried about money.

Armed with financial expertise and first-hand exposure to how people relate to money, her debut book Worry-Free Money: The Guilt-Free Approach to Managing Your Money and Your Life (Collins, $21.99) gets to the heart of modern financial anxiety and guides readers toward feeling good about living within their means. Acknowledging that “life is messy and expensive and never follows the rules,” Simmons provides a liberating approach to personal finance that allows for saving and enjoying life without defaulting to the frugality mindset.

Addressing the underlying reasons why people feel pressure to spend, Simmons teaches readers to identify happy vs. unhappy spending, explains why traditional budgets make things worse (for real), and warns against comparing yourself to others (aka “the Beyoncé factor”). Making money management fun and interesting is a tall order, but Simmons’ book is a practical guide with a reassuring message: “It is possible to live within your means without hating your life.”

Ratehub.ca spoke with Simmons by phone from her Toronto office.


As a financial planner, you peek into thousands of people’s private lives. Where do you think most people stand with financial literacy — have our parents, school system, and society done a good job?  

Yes and no — I think it depends. It’s important to note that I see people from all walks of life: people with tens of thousands in credit card debt, people are looking to retire with not a million bucks. There are similar problems regardless of their financial situations, which is very interesting to me. I think we know the basics: saving is good, debt is bad. I think parents and media have done a good job of enforcing that, but what I think is missing is the nuances — the specifics and nitty-gritty of “how to.” A client could come in and say “I know I need to pay this off,” or “I know I need to invest,” or “I know I need to save, but I have no idea how to actually do that.” That’s the literacy piece and the strategy behind “how,” and that’s where I feel like I get to exercise my muscle, and also just to educate.

You started noticing a drastic increase several years ago in clients using the word “broke,” notably among what you call the “financially frustrated middle class.” Why do so many people feel broke, even if they earn a stable income?  

I think that there’s a couple of reasons. Number one, life is feeling more expensive because there’s an intense pressure to spend money. I blame a lot of that on social media. It seems like a lot of people have it going on, and all of a sudden you open up your email and you’re following a retailer and there’s a sale here, and you turn on the TV, and there’s another thing you need. It’s a non-stop barrage of “Here’s how you’re inadequate in so many ways. If you buy this thing, you’ll be better.”

Combine that with the rise of precarious work and stagnating wages – those are the economic realities. Especially in some urban centres like the GTA or Vancouver, where a lot of the jobs are and the housing prices are bananas whether you rent or own. We’ve got these financial lemons which are out of our control, like housing prices and the cost of living your life. Combine that with this really intense pressure to spend money, and we feel like there’s never enough, ever. I think that’s the feeling of broke, where you just feel like you’re scrambling and you’re never going to be able to relax. That’s what people mean when they say broke: “I want to stop worrying so much that I’m not going to be ok.”

You note in the book that “behind every great photo is a bill,” which you tackled with your Real Selfies Project. Do you think it’s possible to have financially honest social media? Would that be any fun?

No, it wouldn’t be. I’m all about being super honest about your finances, and the effect it had on me was positive and negative. It definitely made me reign my spending in because I felt super accountable to myself and to this project to be honest. It stopped me from buying things because I was like “Ugh, that’s kind of embarrassing. I don’t want people to know I spent that money, and I don’t need this thing, and it’s kind of expensive.” It brought up a whole bunch of feelings.

What I think is what could be powerful about financially honest social media is it would actually have people not spending as much money. It would be frustrating, and you would think more than twice about what you’re about to buy if you had to be honest about it. That could be a positive thing, but it’s no fun. I felt like I couldn’t wait for it to be over. It was very vulnerable, and I felt really afraid every time I posted something that someone was going to judge it. That’s why we don’t talk about money, right? To one person, they’re like “I do that too, that’s funny.” To somebody else, they might be like “Why are you spending $10 on green juice? You’re so financially irresponsible.” Every time you post something, you put yourself out there to be judged, if people know how much things actually cost. It would be a wonderful thing, but I don’t know if it would be that fun unless we all did it — then it would normalize it.

What financial roadblocks do today’s 20- and 30-somethings face that their parents didn’t?

The fixed cost of living is more expensive, like housing and transit, and the job market is worse. The actual economic reality of the hand we’ve been dealt is more difficult. On top of that, our expectations of what life should be is higher than theirs. If you think about 15-20 years ago, they might have gone on one vacation every few years. Now it’s like, “Where are you going on March break this year?” It’s every year. And if you don’t do anything on March break, you can’t post things, and everyone knows you’re a boring parent. That’s not real, and those may not actually be the facts, but that’s how it can feel. When we feel inadequate, we usually spend money that we don’t have. Even though no one is saying those things to you, and it’s kind of in your head, it doesn’t matter – it still makes you feel like that.


“The fixed cost of living is more expensive, like housing and transit, and the job market
is worse. The actual economic reality of the hand we’ve been dealt is more difficult.”


What about what people spend on their kids? Is there pressure to spend more?

That’s another example of the pressure to spend. If you look back 15 years ago, no one was getting professional photos of their belly, and then their baby, and their baby’s one-year birthday. Now, it’s kind of the norm. I didn’t do those, and that’s not to say that I’m better than anyone or anything like that, it’s just not my thing. People were asking me why I didn’t, and I felt like I had to defend the position, and it made me feel like an anarchist – like I didn’t love my kid, or wasn’t proud of my pregnant body… all these feelings came up. That’s what I’m talking about: the expectations of what we consider normalized now. When you veer from what’s normal, people look at you and say, “Why aren’t you?” I don’t think people are getting photoshoots like that so they can keep up. It’s a lovely thing to do, and it makes them feel good, and they’re proud of it. But 15 years ago, that’s hundreds of dollars that would never have been spent.

A lot of people who have overspent on housing that I see in my office, it’s when they get pregnant. I understand that — you want to nest, you want to know where you’re starting your life, where your kid is going to go to school, where’s all that stuff happening. If you rent, it can be nerve-wracking. What if your landlord sells the place? You want to buy something so you can start your life, and we’re in this climate where housing is very expensive and you end up feeling like you have to make decisions and think “Screw it, I have to do this.” Then you end up with a big mortgage and a 25-year amortization period, and you’re really stressed out. It’s a whole chain reaction.

Even though you’re a financial planner, have you been feeling that pressure as a new parent?

Oh gosh, yes. The gear, the gear! It’s so expensive. I look at photos of my friends when they were kids, and from when I was a kid, and it’s like, there was one garbage stroller that I could have fallen out of at any time. There was no UV protection! It was so much more relaxed. Now, the expectation of what it means to keep your kid safe and what it means to be a good and thoughtful parent, and the convenience that these products offer, it’s a lot. And they’re all expensive. I feel inadequate all the time. I took a lot of hand-me-downs from my sister, because my sister has two kids. And I have a lot of friends who have babies too, and they have all this great gear. I see how convenient it is, and it makes their life that much easier. It’s fast, efficient, it looks great. I feel like “Oh my gosh, I’m not a good mom.” I say that as an over-exaggeration, but in that moment it can make you feel like you need to spend money so you have the better gear, or at least live up to the standard that’s been set.

Do a lot of people focus on nip-and-tuck frugality rather than building wealth?

Yes, and I definitely attack the frugal mindset in the book. I think the frugal mindset makes things worse, because it’s not realistic for so many people. Sure, there’s 5% of people who love that game and it’s really effective and makes them feel empowered and in control. For those people: kudos, and keep doing what works for you. But for the vast majority of people I’ve met, that’s not realistic for the way they live their life. It often sets people up to fail, and then they feel like they’re bad with money. It’s enticing because it makes you feel in control of what you can do tomorrow. A lot of the times money problems are big — it can take years to save for a down payment, and it can take years to pay off debt. If you’re looking for a quick win, those tips are things people use to try to get under control. But what happens is it’s not sustainable, and you end up having that quick win, and then you fail again, and then you give up. I’m really against it for the vast majority of people who it’s not working for, because it promotes a lifestyle of guilt.

In my practice, a lot of the people I see are in their late 40s, early 50s. The feedback they’re giving me on the book is that they also relate to this. I think it’s a human nature thing. I think millennials have been painted with a brush of selfishness and narcissism and “I want my coffee and my avocado toast.” That’s the current way that we’re viewed, which sucks because it makes you feel guilty about having a freaking coffee. And there’s nothing wrong with that, if you can afford it.


“There’s always going to be someone who’s more frugal than you, there’s always going to be someone smarter than you at finances, and there’s always going to be someone who knows better. The problem with finances is some things are black and white, but a lot of it is subjective. What does success mean to you? What does financial security mean to you?
It’s not black and white answers.”


In your opinion, what are some of the most overused but minimally helpful financial tips?

“Don’t rent, you’re throwing your money away.” It’s still said by many people, even though there’s tons of articles and journalists out there saying “Um… maybe not.” Especially in this climate where you have these ridiculous home prices. There are things people don’t see behind the massive equity payouts when somebody sells a house worth a million dollars. First, you have to sell your house to have that million dollars — that’s one piece that nobody stops to think about. Second, the amount of money that I see flowing into maintaining a house — repairs, maintenances, endless Home Depot trips — nobody accounts for that. I’d love to see a Real Selfies about that too — every time you go to Home Depot, post that receipt: “This is what home ownership is.” A lot of people don’t see that. So if you’re renting and that truism comes across, you instantly feel bad with money, and silly and stupid. That one really grinds my gears. I hate the pressure to buy stuff you can’t afford. It really promotes people who are just barely able to afford it making the plunge when maybe they shouldn’t.

I also hate the banging of the drums during RRSP season. Again, for a lot of people, the RRSP is great. But I see people who, even if they have a high income, don’t even have an emergency account. They’re constantly living paycheque to paycheque. It’s like, ok, maybe it’s not the best idea right now. Maybe it is next year, or maybe it was last year, but this year it’s not. Especially for people who are precariously employed. Like I said before, saving is good, but it’s the “how.” Every single person needs to assess their own situation for that year. Nothing should just be without strategy, out of fear, or reactionary. I see a lot of reactionary march toward dumping money into an RRSP, and then regretting that.

How do you feel about those newspaper and magazine stories where people share the breakdown of their incomes and spending habits (some of them unpopular, or not smart), only to be shredded by strangers in the comments section or on Twitter? Is that a helpful kind of financial honesty?

No. I feel like the shredding on Twitter is awful. I actually think the trolls are a huge problem, because you have someone who just took the first step in being financially vulnerable and honest, and to have people rip it apart confirms that you should never speak honestly about money. There’s always going to be someone who’s more frugal than you, there’s always going to be someone smarter than you at finances, and there’s always going to be someone who knows better. The problem with finances is some things are black and white, but a lot of it is subjective. What does success mean to you? What does financial security mean to you? It’s not black and white answers. How can you have an opinion on what somebody’s going to do? That just validates the idea that everyone should shut up, keep your money to yourself, and no one should share anything, because if you do, you’re going to be taken down. That’s so sad and devastating. For every person who trolls that person and rips them to shreds, there might be others who are thinking in silence “Oh my god, that’s me.” Then they see the comments and think “Shut up, don’t ever tell anyone.” Disagreeing is one thing, but being ripped to shreds and made fun of is a totally different thing.

Who are some personal finance or investing writers, bloggers, books, or websites that you’re into right now?

I love Jessica Moorhouse’s Mo’ Money podcast. I love Rob Carrick’s blog, Barry Choi’s travel and money blog. Wealthing Like Rabbits is a great book as well – it’s a funny financial book. There’s so much good out there, and I think people are finding that.

This interview has been edited and condensed.

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