The Most Expensive Vacation I Never Took

You know what’s awesome? Booking a trip to Vegas. Less awesome? Not actually taking that trip. The least awesome of all? That trip you didn’t take (combined with bad habits) landing you into years of credit card debt.

I wish I could tell you I was making this up, I really do. But nope – this happened to me back in 2008 and was one of the catalysts to landing me in credit card debt.

Mistake #1: Trusting Drunk Dave

When I was in college one year, I was living with 5 other dudes. Yes, 5. Three of them were named Matt, and two had the same last initial. It was a very complicated period of time, and we drank. A lot. Do you know what happens when a bunch of drunk college-aged guys who just turned 21 decide to talk about Vegas? They book trips to Vegas that they can’t afford.

That’s precisely what happened one spring evening in 2008. Despite my heavily intoxicated state, I remember the conversation somewhat well. We were talking about Halloween and how, now that we were 21, it;’ be nice to enjoy it somewhere where we could legally drink. We’d all been to Madison (though never together) before, and wanted to do something equally fun.

One of my roommates had taken a trip to Vegas shortly before, and had convinced us that it would be a good decision to go. Pumped up on cheap beer and adrenaline, he calls some hotel (I forget which) to book us a room. I, of course, take care of the flights. For all of us. Because that was a smart idea…

Mistake #2: Not Collecting Money ASAP

So here I am, busting out my credit card for the purchase of four flights to Vegas. The flights weren’t particularly expensive, but they weren’t exactly cheap either. Being booked for Halloween put a bit of a premium on them. Instead of asking for money immediately from my roommates, I decided for some reason to wait. This was a horrible decision. It turned out that not all of my roommates could afford to pay me right away; not too surprising but I was stupid enough to think that it’d be fine.

Not collecting the money they owed me right away meant I didn’t have enough cash to pay off the card. That resulted in me starting to just make minimum payments – a big no-no that cost me hundreds of dollars in interest. Ugh.

Mistake #3: Not Looking At My Budget

Here’s where things really start sucking. In 2008 I had a job making barely above minimum wage (averaged about $10/hour with commissions factored in). I knew that the flights and the hotel would be costs that I’d struggled to cover, but I didn’t even bother to look at my budget and consider if I had enough money to do anything in Vegas when we were there. A couple weeks after booking, I crunched the numbers to see how much money I’d have.

The result? There’s no way I would be able to spend any money on entertainment in Vegas. For a city known for its wide breadth of entertainment options – shows, just hanging out at the casino, drinking, etc – this didn’t seem like any way to spend a trip.

I decided then that I wouldn’t go on the trip. It didn’t sound like fun to be stressed about the money. There’s no way I’d be able to enjoy my time there if I didn’t have money to spend, so it just wasn’t worth it.

Mistake #4: Not Paying Off My Card When I Got Money

With the new revelation that I couldn’t even take this trip, I decided to find another of our friends to go in my place. One of the Matt’s who was going along did the same, and we switched our tickets to their names. This transfer cost us $75 a pop, but it was better than going and spending more. Besides, the two people who decided to take our spots paid me for the airfare so that was a plus, right?

Well, kind of. But they paid me in cash, and there’s actually little more in life that I hate than cash. I have this weird problem when it comes to keeping Benjamin’s in my pocket. If I have cash on me, I spend it with no regard to my budget. It just disappears, often to things like food I don’t need, or beer. To this day I pay for everything I possibly can with a card, because I’m just not wired to handle cash responsibly. For a personal finance blogger, this is kind of a tough thing to admit, but at least I learned this and can do something about it.

Years of Recompense

From there, it was downhill. I struggled throughout the remainder of college to pay off my credit cards, and when I graduated in 2010 I had piled on more. As in, about $10k total. I haven’t gone through to do the math on how much that drunken night screwed me over financially. To be honest I don’t want to – no point in dwelling on the negatives of the past.

But it did have a significant impact on me. It ate up a considerable portion of my income post-graduation as I aggressively paid down the debt. When my car died due to a faulty gasket, I had to buy a new car in order to get to work. Unfortunately my piles of debt and relatively low income left me with a crappy interest rate on a car loan – 13.5%.

Between the car loan and the interest on the credit cards themselves, it’s likely that that one drunken night cost me thousands of dollars over the course of those three years. It sucks, making stupid decisions, but every mistake comes with a learning experience.

Lessons Learned

Since then I’ve made some big strides, and the lessons I learned have put me in a much better position financially. For starters, once I finally paid off my credit cards, I was out of credit card debt and vowed to never get back in. Seven years later and I still haven’t. I hated my debts so much that I paid off my high-interest car loan in about a year and a half.

I also made a new rule for myself when it comes to spending money. Any time I want to buy something, I need to budget for it. If it’s not in the budget, I don’t get it then. If it’s something I really want, it’ll have to wait until the next month. This tends to work really good for bigger things, but I admittedly let some of the small stuff slip. It’s not landed me in hot water yet, though, and I feel much more confident in where I am now in regards to how financially responsible I am.

The last major lesson is that sometimes, as good of an idea as something may seem, it’s important to really evaluate my decisions. An impulsive vacation is definitely a costly mistake, and I’ve avoided several others by taking the time to think about what I’m doing. How will large purchases impact my ability to save money this month – and what impact will that have on my retirement plans?

Everything we buy delays retirement, even if only by a small amount. Some of those things are worth it, while others are not. A trip to Vegas that I didn’t take? Yeah, that screwed me over big time. It was an expensive way to learn to not be an idiot.


What are some of your stupid financial decisions you’ve made? How did you recover?

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  1. Oh nooooo. It hurt to read this–I’m sorry this happened to you! We all make dumb mistakes in our youth, don’t we? In fact, I just avoided a stupid, expensive trip to Vegas myself. Mr. Picky Pincher had to talk me down from the ledge of spendyness because I wanted to fly to Vegas on a whim and have fun this weekend. But, alas, it’s far too pricey for our budget so I didn’t make the mistake. Phew.

    1. Haha, at least someone talked some sense into you first!

      Yeah this was a painful experience that cost me a lot of money, but honestly you live and you learn. I was 21, and as long as I’m not making the same mistakes at 31, I’m happy. It could have been much more expensive of a mistake, too, if I had actually gone!

  2. WHERE DO I BEGIN? Unfortunately, good money handling was a skill that I had to learn on my own (still so much to learn). So, I’ve made a ton of mistakes. The biggest one is allowing myself to become everyone’s financial Mother Theresa (she died a wealthy woman, few know this). Currently, 28 years old, and fresh out of college I was the philanthropist. I had my own debt, dreams, and goals. But, they were always being deferred for others. It stressed me out and always left me hanging with the shortest stick. Still recovering, only God knows what kind of lost I’ve sustained because of this people pleasing choice that I took. I’m learning to say “np” and it’s liberating.

    1. Wow – that sounds tough! But helping others is at least better than just squandering it away on frivolous purchases. Saying no is definitely difficult sometimes, particularly in situations where you ‘could’ say yes.

      Thanks for reading and commenting!

  3. Thanks for telling this story. A lot of PF bloggers are quick to tell you how you should do things, but never admitting their mistakes for fear of embarrassment.

    My worst financial mistake was buying the stock of a bankrupt company. I thought for sure they would turn it around! Instead, the court cancelled the stock and its value to fell to a straight $0. Now I only invest in large, high quality companies.

    1. Yeah, that was what I noticed too. Nobody likes talking about failures, especially when it’s what you do (finance bloggers talking about financial fails). But, it is important to talk about things that we don’t do perfectly. I think it makes us more relatable and lets people realize that sometimes everyone makes mistakes.

      That’s a rough deal with that stock. That’s a big reason I stick to index funds, to avoid that sort of thing!

  4. Wow thanks for sharing your story! We learn the most lasting lessons the hard way don’t we? It’s great you realized that not going was a better choice, as you said it could have been far worse. You could have come home with thousands more in credit card debt from booze, food, & gambling too. Way to turn it around and dig yourself out! And your future will be so much brighter now that you’ve learned and are living out those lessons and sharing with others.

    1. Yep, now we make sure to plan for and budget all of our trips and never have to worry about spending too much on them! 🙂

      Thanks for stopping by and commenting!

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