There is an never-ending supply of articles on smart money management, budgeting and all those other important things you need to know to stay out of debt. But what about an article about expensive mistakes? I know I have made a few in my day – hindsight is always 20/20, right?

In this week’s column, I take a look at my costly mistakes and hope that maybe you can learn from them.

As a pretty frugal individual who has always placed an importance on smart spending, I think it’s okay to splurge on things such as travel, art, and entertainment. Spending on hobbies and interests usually doesn’t come back to bite you in the butt. The things on this list are more careless mistakes based in inexperience.

Being Indecisive About College

Finding the perfect college is not easy, but if you put off the decision process, it can be a major financial setback. While I should’ve been deciding on schools and applying for scholarships, I was too busy fighting with my parents about whatever it is teenage girls fight with their parents about.

I ended up choosing to go to the University of Missouri at the absolute last minute which made me ineligible for scholarships I would have otherwise been able to get.

Mistake Cost: $10,000

On a side note, I did end up saving close to $50,000 on my college expenses.

Not Predicting Travel Needs

I have always been a firm believer that buying plane tickets is a strategic game. Last year I was flying home for the first time (I usually drive) and stupidly waited until the very last second to buy plane tickets.

As I slowly watched prices climb, those “last-minute deals” never came to my rescue. I think you can definitely find a break in pricing when booking a flight last minute, but this is not the case when it comes to major holidays such as Christmas. Many flights are booked to the core, and the airlines know they have you in the palm of their hands. My last minute wait ended up costing me about $200 more than I should’ve paid.

Another thing I didn’t take into account was weddings that required my attendance. Although it may seem like a strange thing to predict, every 20-something should budget out travel expenses for when close friends are getting married. I attended three weddings within a few months of each other, and I didn’t account for them earlier in the year. Because of this, I ended up traveling for leisure and spending money that I should’ve saved for wedding-travel expenses.

Mistake Cost: $200-$300

Getting A Tattoo

I am a sucker for tattoo culture. I’ve always thought they were cool, but there is a definite fine line between trashy and cool — some may argue that they are all one or the other.

Unfortunately, I completed my duties with the college-rebel stereotype and got a very small tattoo of which I am not the biggest fan. While researching removal prices I found that getting rid of my little tiny tattoo would cost anywhere from $400 to $600 a treatment. As if this wasn’t expensive already, treatments typically take around 7 visits to complete.

I don’t 100% regret my decision to get a tattoo, considering I was a pretty big square my entire life and this is/was a small reminder that I can be rebellious also. I just wish I chose a less permanent way to rebel.

Mistake Cost: $2,800 – $4,200

Not Looking Into Dental Insurance Plans

When you are young and in college, thinking about dental insurance is the last thing on your mind. Unfortunately, I needed to get two root canals within a year of each other. Instead of taking the time to research affordable dental plans or discount dental services, I just went and paid out-of-pocket. I found out later I could’ve used a service that cost $70 a year and offered deep discounts to subscribers.

Mistake Cost: $1,500 (the amount I could’ve saved).

Ignoring the Rules of the Road

After having a license for four years without any tickets, I got two speeding tickets within a month of each other. I moved to New York City and sold my car thinking that I wouldn’t have to worry about it again. Then, I ended up getting a summons for biking on the sidewalk.

Although no one intentionally gets a ticket, people sometimes fail to learn certain laws. For example, my biking ticket; I had no idea you weren’t allowed to bike on the sidewalk — which in hindsight makes sense. If you’re moving to a new city, make sure you brush up on the rules so you avoid getting arbitrary tickets.

Mistake Cost: $300

Nothing to shatter your confidence like writing an article about all the expensive mistakes you have made. Oh well, live and learn right guys? I hope everyone has a happy and mistake-free holiday!

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  • Randy


    Thanks for the great article; I think stories about our own experiences can be the best and most helpful to others.

    I don’t think that any of us has not made financial mistakes, I know I sure have.  Hopefully we learn from those mistakes; I am still learning and still trying to do better and I think this will be a lifelong journey.  There is so much to keep track of!

    Have a Merry Christmas and the best New Year.


    • Randy,

      Thank you for your kind words! I strive to present interesting and relevant content in new ways, and I am glad that you took notice. The best thing you can do is never stop learning (or at least that’s what I think). 

      I hope you had a good holiday and enjoy your New Year!