Stepping Over a Dollar to Save a Dime

Stepping Over a Dollar to Save a DimeWhen I moved into my first apartment as a college student, the office told me that I could pay $20 a semester to park in the complex’s parking lot, or I could find a spot along the road. Wanting to save a few bucks, I decided to forego the parking spot. Within a couple of weeks, though, I got my first parking ticket. You see, when your school has 32,000 students, you’ve got to have pretty darn good timing to find a parking spot within a mile of your apartment. The perfect spot I found happened to be so perfect because it was a no parking zone.

$30 later, I decided I had learned my lesson. I would park in the school lot kitty corner from my apartment complex. No one seemed to park there long-term, and it seemed too good to be true. Because it was. At least that’s what those signs that said no parking between 11 p.m. and 5 a.m. seemed to mean. Another $30 and it was time for me to actually learn my lesson–I bought a parking pass. Talk about stepping over a dollar to save a dime.

I’ll be honest, I really suck at this (if you haven’t already noticed). Trying to avoid a $20 parking pass isn’t the only way I’ve screwed myself into paying more. Here are some other areas I’ve failed, and I think they’re definitely areas where other people would be tempted too.


Our last year in college, when we found out that we could switch to our parents’ insurance plans until age 26, we dropped the university-sponsored health plan, which was about $100/month for the both of us. I knew what my parents’ health insurance entailed, but failed to ask about her parents’ high-deductible plan. We ended up learning the hard way when she visited the emergency room twice in two weeks, the first time because of a concussion she received during a basketball game, and the second when she herniated a disc in her back. In trying to save $100/month, we ended up spending over $6,000.

To be clear, it’s not my in-laws’ fault they had a high-deductible plan. And that’s also not a knock on high-deductible plans in general. It works for them because they rarely have to use it and can largely self-insure on the small things. But since my wife had already been through the wringer with physical ailments, it would have been a lot smarter for us to stick with the plan the university offered. The moral of this story is take more than the premium into consideration when deciding if insurance is worth your money. Whether you believe it or not, bad things happen. And it’s not just health insurance. We’re talking life, auto, disability, renter’s, homeowner’s, etc. Don’t screw yourself in the long run to get out of little costs up front.

Vehicle Maintenance

Neither of our vehicles have seen a mechanic in years, because I’d rather avoid the maintenance costs and just hope the lack of attention doesn’t lead to a major breakdown. But I know deep down that my avoidance over the last few years has already caused irreversible, even if gradual, damage. Because our cars haven’t been properly maintained, I’m afraid to drive down to New Orleans in a couple of weeks to go to FinCon. I’m also afraid for my wife to drive across the country with her friends to a conference next month. Nothing major has happened yet, but I can hear the subtle ticking of the time bomb.

Buying in Bulk

I’m definitely a fan of buying in bulk. My wife and I actually just visited Costco last night to get us enough toilet paper to survive until our unborn child’s 16th birthday. But there can be dangers in it as well. For example, the last time we went to Costco, we got a 20-pack of Greek yogurt. We were on a yogurt kick and decided to score the $0.60 per cup deal instead of buying them individually at Kroger for $1.00 a cup.

The only problem is that we couldn’t eat them fast enough. I tried freezing them, but after a week or so of that working out, the consistency became nastier and nastier until I couldn’t take it anymore and threw the rest away. Moral of this story? Buying in bulk is a great way to save some money, but don’t bite off more than you can chew.

Overdoing the Discounts

Deals don’t last forever. In fact, daily sales and discounts are engineered to force you to make a quick decision. I got into trouble with this when we were in college when Groupon first came out. In my desire to save, I bought more and more of them–mostly on things we didn’t need in the first place. Some of them were completely forgotten and expired before we had the chance to use them. We ended up paying more just to get the discount on things we could have gone without.

Investing in Yourself

Outside of my freelancing, there are a number of side hustles I’ve considered doing. But I’ve always been hesitant to invest the necessary amount of money into potential side hustles because I’m afraid I won’t get the money back. Being that cautious makes for a difficult run at entrepreneurship. Of course, no entrepreneur is without his or her failures, but you miss every shot you don’t take, and you’ll never get the dollars without spending the dimes. The same goes for other investments into your future.

One of the reasons I’ve avoided the thought of going back to school to get an MBA is because of the costs associated with it: tuition, not having a job (because there’s no way I’d be able to work full-time, do an MBA and do my freelancing), and all the expenses that come with living. But when I recently posted something on Facebook, a friend of mine said that even though her husband was unemployed for a while after receiving his MBA, now that he has a job, he’s probably 6-7 years ahead of where he would have been without it. Obviously, there’s a cost analysis that has to go with that, but it’s generally not a bad idea to jump start your career and earning potential with a little investment.

Are you guilty of stepping over a dollar to save a dime here and there?

(photo cred)


14 thoughts on “Stepping Over a Dollar to Save a Dime

  1. Right on the money, Ben! In economics terms, this type of behavior is called “false economy” where you try to save a buck now but end up spending ten later.

    I personally have been a guilty practicer here and there. For instance, I’ll have a number of how much I want to pay at the grocery store for food, so I’ll only buy items to cook three big meals a week. No snacks, no nothing. But then, after I make my food, I still get a little peckish during the day. If I had the foresight, I could have just bought some nuts and cheeses at the store instead of hitting the Asian bakery down the street, which definitely did no favors to my wallet or waistline.

    1. I’m guilty of that as well. I decided last month it was smarter for me to buy a couple 12-packs of soda for $6 to last me through the month at work rather than hitting up the vending machine every day at $1 a pop.

  2. Interesting read. I am surprised that yogurt went bad so quickly. Usually yogurt is just fine well past the date stamped on the carton. After all, yogurt is technically already spoiled, so as long it’s kept cold to prevent curdling, it should have stayed good.

  3. I’m guilty of this as well, all summer actually with NYPD/parking tickets! When it comes to investing in yourself, as you said it’s about figuring out if the cost will be worth it. I recently did this when I became a freelance writer. I decided to pay for coaching services and it’s already proven beneficial for me in terms of money and improved writing ability.

  4. I am so guilty of this. I think part of it is that I’m too stubborn =). I need to show my car a little love as well, because we’re also driving to FinCon. I’m a little worried, but four months ago it made a longer trip like a champ, so I’m hoping things will go fine. I hear you on investing in yourself. I’ve spent a little bit on freelancing courses and coaching as well. Most programs offer 30-day money back guarantees if you find it’s not the right fit!

  5. Am guilty of this as well…maybe because am always looking for a bargain that at times I miss the bigger picture 🙂
    Am a huge believer of investing in oneself. After all, that stuff between our heads is the greatest financial asset we have after all, its what mints all the other wealth. Any opportunity I get, I try grow myself a little bit more, and it keeps paying in leaps and bounds.

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