3 Weirdly Specific Spending Mistakes [2025]

Let’s clear the air immediately on this one – I realize there’s an inherently judgmental tone when discussing spending “mistakes.” After all, it’s your money, not mine, so at the end of the day, who am I to call something that you’re doing a mistake?

Here’s why I’m dubbing these decisions “mistakes” – because I think you’ll agree. There’s a difference between spending decisions that are unorthodox or may seem objectively irrational when compared to the average, but still aren’t mistakes for you.

But then there are things that you’d probably stop doing if you knew better; things that don’t serve you in any way beyond stretching you thinner than you’d have to be stretched.

The genesis of this article was the realization that, for the past year, I’ve seen three extremely common trends in clients – almost without fail, every person makes at least one of these expensive mistakes (and sometimes all three of them). So now you get to benefit from hundreds of hours of consultations #FoFree (should I plug a “Subscribe” push here? Why not!).

I’ve isolated things that aren’t one-off mistakes – they’re consistent, ongoing choices or habits that will cost you thousands of dollars over just a few years’ time.

#1. Overpaying for car insurance

I feel like a Geico commercial right now, but it’s true. When I worked with people 1:1 a few years ago, almost everyone I met was paying through the nose. The majority don’t have any accidents on their record or driving events that would justify $170, $180, sometimes $200/month for car insurance, but I’m telling you, it’s not necessary. What I’m trying to say is: Your car insurance should not rival your car payment.

Most of the time when I ask, “Have you shopped around?” like the broken record I am, the answer is no.

Why? Because it’s one of those adulting phrases that we all throw around like it’s a recipe with a cauliflower substitute but don’t really know what it means.

Let me tell you, though, “shopping around” for car insurance will save you money, big time. The first time I got car insurance in Dallas, I bought a 12-month policy with Progressive for – please sit down – $2,100. I forked over $2,100 in one sitting for car insurance, which is the equivalent of $175/month.

When it came time to renew, I simply wasn’t about it. My ticket-less, accident-less driving history didn’t feel like it should cost $1,800 to insure for a single year.

So I did an experiment: I went into “Incognito” mode in my browser and went through the quote process all over again (it’s easy – just Google [car insurance company name] quote). They were quoting me $1,800 to renew, and when I went through the process in incognito, they quoted me closer to $1,700. It felt so arbitrary.

I chatted a specialist and explained I had been given a better quote and I would very much like that one instead, please.

After another year of this, I got wise and started shopping around in earnest. I finally settled on Geico, where I could buy a six-month premium for $660 ($111 per month).

The point is, you’re probably overpaying, and by going through a few online quotes (you don’t even need to call anyone!), you can almost definitely lower your rate. By doing so, I’m saving $40/mo., or $480/year, but receiving the same level of coverage.

#2. Having multiple gym memberships that are going mostly unused

I’ve been surprised by how many ad hoc gym memberships or other subscription-style programs people cobble together on an ongoing monthly basis.

$100 here, $75 there… it adds up. And this is usually how the conversation goes:

“Ok, so you’ve got a $150 membership to Insert Boutique Fitness Studio Here, but I also see a $75 charge for Insert Drop-In Fitness App Here.”

(long pause)

“Oh yeah, well, I use both because I like to do multiple formats.”

To which I say – FAIR. I am the last person who would ever tell you to commit to OrangeTheory for the rest of your life and kiss a stationary bike or a pilates reformer goodbye.

This is where it’s crucial to do the cost analysis of what you’re paying for. When I used to work at Corepower, I never understood why people would pay $100 for a 5-class pack when the unlimited monthly membership was $129. Of course, I was going every single morning, so if I were paying on a per-class basis, it would be intensely expensive.

That said, you probably don’t need to pay a $150 membership fee for a studio you’re visiting once a week (or even twice a week). Even if you’re going twice per week, you’re paying about $18/class. That’s obviously better than a drop-in rate, in most cases, but just barely – I would recommend dropping gym memberships that don’t truly serve the community aspect for you. If you’re popping in once a week, it’s time to cut the permanent ties and use your aforementioned “Drop-In App” of choice to stop in when you feel like it.

The funny thing about gym memberships is that I’ve found people have a hard time parting with them (even when they’re not using them!) because they represent the type of person you were, at some point, trying to become: the type of person who frequents a boutique fitness studio.

But the sooner you let go of this vision of you that’s simply not working out (maybe you just don’t LIKE CrossFit and “functional fitness” – that’s not a personal failing!), the sooner you’ll free up those #funds to discover that maybe your true fitness muse is actually more of a “heels dance class” fanatic. You gotta let go to grow, my friends.

Of course, we can apply this principle to a lot of things, but the boutique fitness trend has almost uniformly influenced people into signing up for multiple memberships, and most people don’t need more than one.

#3. Sleep-walking through impulse purchases

This is the point of the article where we’re going to transition into dangerous, line-straddling “judgment” territory, but stick with me – the point of this “mistake” is the sleep-walking part.

There is an energetic difference between the way you purchase things you’re obsessed with and that bring you intense and sustained joy, and things you throw in the shopping cart at 11 p.m. on Glossier’s website late Friday night because you’re bored and lonely and that product called “Bubblewrap” sounds so enticing and cozy (not a personal example at all!).

I call these sleep-walk purchases because you’re going through the motions. Something strikes your fancy in a moment of weakness, and before you know it, it’s on your front step three days later, to be toyed with for all of 15 minutes before being relegated to the back of the bathroom drawer, used a handful of times, then never seen again.

The reason these types of purchases are insidious is because they prevent you from being able to spend on things you actually love.

If you feel yourself often saying, I have no idea where all my money went this month, it’s probably stashed in your closet, dresser drawers, kitchen cabinets and bathroom counters, in the millennial pink bottles, oversized cutoff hoodies and S’well water bottles (remember those?) that creepily stalk you around the internet in flashing ad placements.

There’s nothing wrong with buying your fifth oversized cropped sweatshirt or yet another face wash made of the same ingredients as all the other ones sitting in your shower, but if you’re going to do it, do it with eyes wide open – maybe sit for a second and think, Let’s say I didn’t spend $38 on this right now – what could I experience tomorrow for $38 instead? Drinks and apps with someone I haven’t seen in awhile? Two books I’ve been dying to read that’ll give me hours upon hours of entertainment and knowledge?

I’m not even necessarily telling you to not spend the money and to save it, but just to spend on something you’re actually going to derive happiness from.

On a larger scale, we could dive into the difference between spending $1,000 on a handbag or $1,000 on a trip to Southeast Asia, but we’ll save that esoteric discussion for another day.

In closing

While I (unfortunately) can’t write on a 1:1 basis to address all the unique quirks and spending oddities of each specific individual, I feel confident that these three will cover the majority.

I challenge you to see just how much fat you can trim from your monthly expenditures without measuredly changing your life (i.e., are you going to feel super deprived because you have a new car insurance policy or because you remove one iffy class per week from your schedule? Probably not). Think about it like buying back your own time and money from places and things that were sneaky budget drains.

Let me know how much you’re able to trim monthly (then multiply it by 12 to get excited about all the potential you just freed up!).