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My Biggest Money Mistakes And What I Learned From Them

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By my thirtieth birthday, my wife and I were consumer debt free, with a six figure net worth and more than 25% of the way to reaching financial independence. Things have been going pretty well for us the last few years, but we didn’t always make the best choices with our money. 

In fact, I’d go as far as to say we’ve made some really dumb decisions with our money, especially me. 

Here are 5 of my worst financial mistakes and what I’ve learned from them.

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Money Mistake #1: Not Taking Investing Seriously Earlier On

Shortly after I turned 18, I got hired at a warehouse and I was making $16 an hour. Since I  lived at home, my only financial responsibilities were paying for classes at the community college, my car insurance, and my cell phone bill. 

Instead of making responsible choices like saving and investing, I was going out to eat, buying new shoes and all the stuff you can imagine an 18 year old likes to do with their money. 

Looking back on it now, that was the perfect time for me to start investing and building wealth. I just completely blew that opportunity.

I had the employee stock option plan and I would put $50 into it every paycheck, but I never took the time to really learn about my 401k or any other investments for that matter.

When I left this job in 2010, I cashed out all of the stock.

At the time the price was around $45 a share, which was higher than when I started putting money in back in 2008.

I felt like I had done something right because I cashed out while I was ahead. That’s kind of what everybody tells you to do, you know, get out while you’re ahead.

The problem is that the same stock that I was invested in is at about $110 a share today, meaning if I had just left it alone, it would have more than doubled by now. 

Also, had I not bought dumb, unnecessary ‘stuff’ and invested half of my check while I was living rent free, I would have been in a fantastic financial position much sooner in life. 

It wasn’t like I didn’t know that was an option, either. My senior year of high school, I had an  economics teacher that advised us when we started working, we should open up Roth IRAs and put as much money in them as we could.

Then my dad also told me to save up and buy rental property in a rundown area that’s now become this hot spot in Houston. 

Well, the time has come to admit that you were right Dad. I should’ve done that. I should’ve also asked both of these guys more questions.

I should have done more research on my own about different investment strategies that people were trying to push me towards. I just didn’t take it seriously at the time and it costs me tens of thousands of dollars. 

I did  “wise up” and got around to investing, but it was almost 10 years after graduation when I finally did so. The lesson here is to take the time to learn about investing as soon as you possibly can. So you don’t make a mistake like me.

Money Mistake #2: Using Credit Cards the Wrong Way

When I was 21 I landed my first sales job. It was a commission only job and I was excited about it. It was about a year after I had moved out of my parents’ house.

When I started the job, I had a bit of money saved, but I knew that I wouldn’t be making much money early on. So I got a credit card ‘in case of emergency,’ because I didn’t want to have to go back and ask my parents for anything. 

A few months later on a road trip about 24 hours from home,  my car starts overheating on a Saturday night. A mechanic pulls over and he’s able to help us. He gets us a tow truck and takes us to his shop.

Of course, I’m thinking that this guy is a lifesaver! He’s doing this so we don’t have to be stranded until Monday morning. 

When he’s done, he hands me a bill that’s over $1,000. I don’t remember exactly what was wrong with the car, but I know for a fact that it was not $1,000 worth of work. In the moment though, I figured he saved my butt.

I just swipe the credit card and swiped it for pretty much everything else I needed to get home. 

The problem was I didn’t have the money to pay off the entire cost of the repairs. I just started making the minimum payments. 

When I tell y’all that that situation opened up the floodgates, I mean it. After Mr. ‘Nice Guy Mechanic,’ anytime something unexpected popped up, I pulled  out the credit card. 

I could cover the bill every month, so, in my mind, it wasn’t a big deal.

After a while, I became numb to that bill coming every month.

After a little bit of time passed, it stopped being just emergencies and it turned into things that I really couldn’t afford, like vacations and electronics.

Then my girlfriend at the time, who’s now my wife, starts charging too. By the time we got married, we had over $20,000 in credit card debt combined. 

Looking back on it now, I realize that I made two big mistakes with the credit cards. 

  • I should have had at least three months of expenses saved instead of relying on a credit card for emergencies.
  • I shouldn’t have used my credit card to buy things I couldn’t actually afford. 

By the time I started swiping more, I was making $55,000 a year on a salaried position, so there was no excuse.

I should have been on a spending plan, I should’ve been paying this thing off and I should have been paying all my expenses and saving up for things that they came. 

Instead, I was upping my lifestyle as my income increased and I was digging myself deeper and deeper in debt. 

If you’re going to use credit cards, use them responsibly or just stay away altogether. It’s not worth the damage if you don’t have the discipline.

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Money Mistake #3: Keeping Up With The Joneses

We all get bombarded every single day with ads and social media posts that remind us of what we don’t have and where we’re not in life. When that happens, it’s easy to start feeling less than or like you need to do something to catch up.

Insecurity is expensive, friends.

I know this because it’s how I used to live too.

Remember that salary job I was just talking about? One of the first things I did when I got that job was finance a brand new car. Did I need a better car at that time? Yes, definitely.

My car at the time was on its last leg, but I definitely did not need to spend almost $30,000 on a new car. 

Had I not been worried about what my friends, my family, my coworkers, and just the random dude at the stoplight would think, I probably would have gotten a reliable used car for $8,000.

I know that’s true. How?

This is exactly what happened when we were shopping for our house two years ago. We only used my wife’s income to keep us from being tempted into buying too much house and we were still approved for twice our budget. 

We told our realtor to not even show us homes outside of our price range and we eventually settled into the house that we have now.

This house fits our family perfectly. It’s less than half of what we were approved for. It’s right in our budget and because of that decision, we have the flexibility to live on one income if we need to.

The plan is to completely play this house off in nine years or less. That’s possible because we reached a point of not caring what other people think.

So what’s the difference?

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We now know what we want out of life and our spending is aligned with that vision and it’s not aligned with the societal expectations or even peer pressure.

The lesson here is don’t focus on what other people have or what you don’t have.

Focus on building towards your own goals and dreams because in the end that’s really what’s going to lead you to a more fulfilled life.

My biggest and worst money mistakes

Money Mistake #4: Not Talking About Money In My Relationship

When we got married we had a combined $61,000 worth of debt.

To be honest, we did not know that number until our honeymoon. We had been dating for five years at this point and we never had an in depth financial discussion!

We knew we both had credit card debt and we both had car loans, but we didn’t know the exact figures. We never shared exact figures until we were on our honeymoon and we had our first real disagreement about money. 

I knew Taylor wanted to have the option to stay at home when we had kids, but we never discussed what we needed to do in order to make that happen.

We discussed buying a house and even retiring in Europe, but we never talked about what we were going to do to get there.

There was also the fact that I was helping family financially and I never shared the full extent of that with Taylor before. 

You can’t delay these discussions because there’s going to come a time where you’re forced to have that talk just like we were. When you get to that point where you’re forced to talk about this, things get a little testy 

The lesson here is to have those important money conversations before you get married.

Know how much debt you both have, know each other’s incomes and credit scores, and how much you have saved, and whether you’re supporting family members financially.

You also need to know how each other’s individual situations impact the life goals that you have as individuals and the shared goals that you have as a couple.

From there you can start crafting a plan to build everything you want to get out of life together. Whether that’s paying off debt, investing or wherever you need to do, you’ll have a great place to start from.

Money Mistake #5: Raising Our Housing Costs For No Reason

Right before we got married, we signed a lease on this nice, three bedroom house.

At this point, we had no plans to have kids.

While we were in the process of leasing the house, the owners kept dropping hints that they might be looking to sell the house soon.

We rented in hopes that, maybe, when our lease was up, we could buy the house.

We were coming from this super tiny one bedroom apartment to a three bedroom, two bathroom home. 

What do you do when you upgrade your home? You upgrade your surroundings, right?

So we took out our credit cards and bought brand new furniture.

Then we got married and went on our honeymoon where we realized our net worth was negative with $61,000 worth of consumer debt.

Our expenses went up right as we were trying to lower them to become debt free.

These decisions less than a month before our wedding made our journey out of debt so much harder and longer. 

Looking back on it, what we should have done was be content with the little one bedroom apartment we had. 

Our focus should have been on using that time where we didn’t have kids and we had limited responsibilities to get out of debt and start building up our wealth.

Instead, we let impatience lead us into a bad financial decision and that costs us some time and some money on our journey.

Thankfully that lease was only for a year and we were able to move back into a small apartment. That decision helped us finish our debt free journey and ultimately grow our net worth by $100,000 in two years. 

The lesson here is to be patient, stay content with what you have and where you are. Don’t rush into big financial decisions for any reason other than it was a personal goal you had and you’ve saved enough or you’re in the financial position to be able to do it. 

At the end of the day, all of these bad mistakes come from one thing, not having a long term plan for my money. Maybe you’ve made some big mistakes that you are paying for right now. 

You’re not too old to turn things around. You’re also not too young to start being responsible.

The best time to start taking charge of your finances is right now. 

We all make money mistakes. I share 5 of the biggest and worst money mistakes I've made over the years

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