Why so many of us tend to financially sabotage ourselves

In 2015, Alyssa Fischer decided to tally up her spending — and she didn’t like what she found. Over the past six years, she’d spent $7,617.13 on clothes, $3,863.57 at restaurants, $2,047.90 on parking and $1,693.53 on iTunes purchases. The total? More than $15,000 — all on things that Fischer didn’t consider essentials.

By the time she shared these figures on her blog, Fischer had already decided that enough was enough. “It was reckless spending if I'm being completely honest,” she told me over email in July. In those years, she had relied on credit cards. “It was a never-ending funnel of earning enough to pay the monthly minimums and spending what small amount of space was left on the cards to get me back to the maximum.”

The logic that helped her justify spending money she didn’t have during those years was not, in retrospect, really “any logic in the slightest,” she said. “It was just me ignoring the fact that I had a ton of debt… I figured that because I was young, it didn't matter what I did with my money right now.”

“I never imagined that I would need retirement savings or want to buy a house one day,” Fischer added. “Those things all seemed like an eternity away and therefore I never blinked an eye.” 

If Fischer’s story seems relatable, you’re not alone.

Liz Schieck should know. A financial coach and planner at the New School of Finance in Toronto, Schieck has witnessed her fair share of financial woes. Fischer’s “fuck it” approach to finance is not only common, she says, but something that actually happens “all the time.”

“People reach a point in their life where they’re like, whatever. This mess is so big and so wide and so tall, it’s insurmountable… I might as well enjoy myself,” says Schieck. “If I can’t get to where I’m going, I might as well have fun.”

Based on Schieck’s experience with her clients, people who approach their finances this way have one critical thing in common.

People reach a point in their life where they’re like, whatever. This mess is so big and so wide and so tall, it’s insurmountable… I might as well enjoy myself

“When I ask people at the start of our meeting what they’re hoping to get out of it… they either say that they want to get some financial literacy, or… [that they] don’t know anything about money. And very often it’s not true at all,” she says. “As we go through the meeting, I’m like, you know so much.”

In other words, people who take a pessimistic — and sometimes even self-sabotaging — approach to their finances are not doing so because they don’t know any better. So what’s actually driving their attitude?

The answer, it turns out, is twofold. On the one hand, many people are legitimately struggling. Relative to the salaries that people are making on average, the cost of living is high — especially if you live in an expensive city like Toronto or Vancouver. Between housing expenses, commute costs, insurance, student debt and childcare — for which Schieck “routinely” sees people paying “anywhere between $2,000 to $3,000 a month” — what seems like a decent salary upon first glance can quickly start feeling like the bare minimum.

It doesn’t help that some people have been able to get by on comparable salaries — especially in the recent past. “People often know someone, or who have friends who are maybe a little bit older, or who started their career a bit earlier, so maybe they bought a house earlier, or they had their kids a little younger… sometimes people ‘got in’ before it got so expensive,” says Schieck. “So they’re comparing themselves to their peers or to other generations and going, well, they seem to be doing ok, so what am I doing wrong?”

That brings us to the second reason why so many people seem to take the cynical view. With the ubiquity of social media, it’s become easier than ever to compare ourselves to others and feel like we don’t measure up — even when we know that we’re only seeing what Schieck calls a “curated version of people’s lives.”

“What I see is that a lot of people are having a hard time, but every single person is saying that everybody else seems to be doing great,” she says.

“So we see that someone’s gone on vacation, and we think man — when was the last time I went on a nice vacation like that? What are they doing that they can afford that, that I can’t?”

When people feel like their debt or their financial goals are insurmountable or unachievable, it is often because they’ve already tried to reach them a few times, and felt like they failed

Still, social media only exacerbates a problem that existed long before the word “feed” became a part of the common lexicon: it’s still taboo to talk about money. As a result, it’s easy to get the impression that everyone else has their act together, and that you’re the only one struggling. And from there, it’s hard not to start wondering why you’re failing — and start feeling bad about it.

“I really encourage people to talk more about money,” says Schieck. “There’s really interesting results, you know. A lot of times people say they bring it up with their friends, or with some group, and everybody’s like, oh my god, you too? I’m so glad we’re having this conversation because I thought it was just me.”

Schieck says that Shannon Lee Simmons, the founder of the New School of Finance, often tells a story that demonstrates how receptive people can be to talking about money — even if they might be reluctant to bring up the subject first. Relatably, the story involves Lee Simmons being invited to a birthday dinner that she couldn’t exactly afford. “This friend’s having a birthday dinner at a nice restaurant, and you don’t wanna say no because it’s their birthday,” says Schieck. “But then [Lee Simmons] actually brought it up at the dinner, like — was this hard for anyone else? And they ended up having a really great, transformative conversation.”

It’s easy to get the impression that everyone else has their act together, and that you’re the only one struggling

Talking more openly about your financial struggles is one way to turn your attitude around, says Schieck, but it’s also important to figure out your personal triggers. Is it social media? Is it whenever your debit card is declined? Keep track, so that you can either avoid those triggers, or work out a strategy for coping when they do pop up.

The other way to steer yourself away from self sabotaging habits is to look at the root of the problem in the face. Why are you constantly running out of money? Figure it out, and come up with a plan that’s actually realistic, says Schieck.

“When people feel like their debt or their financial goals are insurmountable or unachievable, it is often because they’ve already tried to reach them a few times, and felt like they failed,” she explains. “They had a series of setbacks or what they think of as failures, and so they give up.

“That’s something I see all the time, and it’s usually because the plan — whether it’s a budget or the goals they were working towards — was really unrealistic or not sustainable: very, very aggressive, very restrictive and not something that’s going to be able to be maintained for a long period of time. Because it feels so restrictive, and the goal is so hard to reach, people get miserable really quickly and they give up on that plan.”

Ultimately, it comes down to recognizing that treating your finances as a lost cause can only make you feel worse in the long run, and that you’re not alone. 

Which is exactly what happened to Fischer. After her then-boyfriend (now husband) proposed at the end of 2014, she started looking for jobs to help save money for their wedding — and ironically ended up at a debt consolidation company. “In my training, I sat in on client meetings and listened to people explain their financial situations,” she said. “After a couple of phone calls it finally sank in that I was in the exact same boat as all of these people.”

“A week after I started there, I moved into a cheaper place, went on a spending freeze, created a really strict budget and started my financial blog to hold myself accountable. In 10 months I was debt-free and the happiest I had ever been.”

“You sometimes don't realize,” she added, “How care-free your life can be if you don't have to worry about credit card interest and collection agencies.”

Illustration by Taryn Gee.