Money Mishaps: 12 of the Most Epic Regrets in Spending

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Money can’t buy happiness, but it can cause heartache when we look back on decisions that cost us time and resources.

When it comes to making unwise spending choices, most of us have at least one story (or twelve) about a major financial regret, whether big or small, that would give us an embarrassing lump in our throat if we ever repeated it aloud.

These regrettable situations are more common than you think, from paying too much for something to furthering credit card debt unnecessarily.

So, let’s leave the shame behind and get candid about some of the worst money mishaps people often find themselves in.

#1. Giving Money to Family

Giving money to someone who is struggling can be a good thing.

But you’ll soon discover that not all friends and family members are trustworthy or willing to pay you back.

It’s a common experience for people to give money to those around them only to never actually see that money paid back and witness relationships get ruined in the process.

While it might not be easy to say no, it is the best option in the long run.

#2. Nice Cars

Nice cars are often collector pieces.

They sit around getting dusty, must be turned on occasionally, and require consistent care.

If you drive them around, you put them at risk of further damage on the road or damage caused by other drivers.

Plus, the more miles you put on the vehicle, the lower the resale value.

What’s worse is when people spend thousands on aftermarket upgrades and think they can get a dollar-for-dollar match on the cost of these when they go to sell.

They discover that “beauty is in the eye of the beholder,” and most people aren’t interested in the modifications, forcing the seller to lose money on the deal.

Remember, nice cars are generally not a good investment.

#3. A Business

Purchasing a business can be a great way to generate more income and set yourself up for financial success.

That is until you realize how much debt is associated with the business that you’ve just purchased.

Some have invested in a business and are constantly stressed by how much they owe and how much work goes into it to ensure it doesn’t fail.

Before investing any money into a business, do your research to ensure this is the venture you want to wake up and spend your days doing.

Also, make sure you know what is involved in running a business.

Most entrepreneurs work more than 40 hours a week, with many putting in time on nights and weekends.

You can get to the point where you can hire people so you are not involved in the day-to-day operations, but this is not the case for the first few years.

#4. Individual Stocks

Individual stocks have been great to some and not so great to others.

For those who regret investing in stocks, it is usually because they bought into some hot stock of the day, and their exuberance cost them dearly.

Others usually regret investing because they didn’t keep their emotions in check.

When the stock dropped in value, they worried and sold for a loss.

Had they taken a long-term approach, they could have avoided this disaster and made money.

#5. Log Cabins

Log cabins and homes are cozy retreats for nestling in the hills or mountainside during winter.

When they purchase one, few expect how much work goes into it.

These structures require constant maintenance if you want them to avoid becoming infested or rotting, and they’re often a lot more trouble than they’re worth.

Additionally, if you plan to use your log cabin as a vacation home, many people mention how it is more of a hassle than an enjoyment.

They feel the need to use it, even skipping other vacations, because what’s the point of having it if you never use it?

Plus, there is the high cost of maintenance that leads to regrets.

#6. Apartment Buildings (and Other Forms of Real Estate)

Real estate is where it’s at if you’re looking to grow your wealth.

However, not all forms of real estate investing are a path to quick cash.

If you want something that will continue generating revenue, apartment buildings can seem like a great idea.

The problem?

The constant upkeep and the know-how that comes with building maintenance can take its toll on those unprepared to manage this type of investment.

Plus, you have to deal with tenant complaints, chasing payments, and more.

The potential income blinds many, and they don’t see the daily stress and hassles that come with ownership.

#7. Fine Dining

Very few people realize that fine dining is a spectacle, not a place to get fed.

You receive very tiny portions for enormous amounts of money.

Many who go out to a fine dining establishment leave hungry and poorer rather than satisfied.

This disappointment usually stems from building up the experience in their mind to the point where it can never measure up.

#8. Trying to Impress People

This is a broad example but a sentiment you’ll find most agree with.

It’s natural to spend money to impress people, regardless of whether they’re in a social group we’re trying to work our way into or someone we want to have a relationship with.

At the end of the day, it’s usually a waste of money.

While you will feel good in the moment, you will quickly experience that void.

For some, this void is a wake-up call to stop. For others, they double down on trying to impress to push that feeling down, causing more issues in the long run.

#9. Building a Custom Home

Building a dream home became a nightmare for many.

There are many construction costs, additional property taxes, long waiting times until construction is finished, and having to deal with living costs while you’re waiting for your dream home.

Some regret not spending money to buy a house they could move into immediately.

And as with modifying cars, your home has features that you specifically want. When you go to sell, odds are slim buyers will want the same things, forcing you to potentially sell for less than you were hoping.

#10. Angel Investing

Angel investing is a form of investing in which you give money to startups and receive equity in return.

In theory, you will then reap the benefits of a profitable business down the road.

There are success stories, but there are an equal number of stories of angel investors who wished they had put their money elsewhere.

The reason is that most startups fail, and along with that goes your investment.

#11. Interior Designers

There are good interior designers, but people often hire them to tackle the work before home renovations.

The result is spending a lot of money overall.

A better option is to look at the long-term goals you want for your house and then spend accordingly.

There is no point in updating your bedroom’s decor if, in three years, you plan to knock down a wall and re-arrange everything.

#12. Fancy Cookware

Fancy cookware is often perceived to offer the pinnacle of the culinary experience.

But as someone who enjoys cooking at home, you don’t need the best to do the job.

There are plenty of other basic brands out there that offer excellent non-stick cookware without breaking the bank.

And in reality, you won’t be able to taste the difference. You might think you can, but you can’t.

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In many cases, you can have cash in your hands the same day.

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This thread inspired this article.