I don’t know about you, but I learn a heck of a lot more from my failures than I do successes. When everything goes right, I learn very little. I learn nothing beyond what happened to go right in that instance. But, what about the next?

Here is the difference between successes and failures:

Failures have a way of humbling us. They force us to reflect on the situation, as well as ourselves, to determine where we F’ed up. We retrace our steps and analyze where we stumbled off the path to righteousness. We admit to ourselves that, well, we screwed up. It happens.

And, it’s this process that teaches us about ourselves. About confidence. About picking our asses up from off the ground and trying again. And again.

We all love successes, but we learn so much more from our failures.

What I’ve learned from my failures

I’ve made a ton of mistakes in my life. Shit, more mistakes than I can possibly count. I blew money on stupid stuff. I was brash and over-confident. I did way too much ass-kissing in a previous life than I was comfortable with, all to get ahead in corporate America.

Hi, I’m Steve. And, mistakes were made.

I bought a sports car

A month out of college and after securing my first real job, I bought a $25,000 sports car (a 1999 Corvette convertible). I gotta admit – that car was pretty bad ass. It was the loudest car on the road and definitely one of the fastest. I plunked down good money on upgrades like a supercharger, forged rear end, cat back, long tube headers, twin-disc clutch – you name it, I did it.

My Corvette, now sold

But, it was also a money pit – a pit that seemed to get deeper and deeper after each upgrade. The fact is the more upgrades I slapped onto that baby, the more expensive she got. Things would break. It needed meticulous maintenance. It just wasn’t worth it, and honestly, I had no business driving around in a car that cost half of my first year’s salary right out of college.

Oh, I also rode around on a Yamaha R1, one of the fastest sportbikes ever made – nearly killing myself on several occasions. Insurance alone was around $150 / month. But, I didn’t care. I wanted the bike. I loved riding it, and I was prepared to spend any amount of money to continue doing it.

What I learned: Cars are not investments. Cars are machines, and we should use those machines to support the things necessary to maintain our lives. Like commuting. Or picking up groceries. Or…whatever. Now, I use cars for what they truly are…a utility!

I went out to eat a LOT

Over the first three or four years of my professional work life, I went out to eat for every meal I ate. And when I say every meal, I actually mean every meal. Every damn meal.

Let’s just say that my roommate and I had the cleanest kitchen in the entire apartment complex. We just never used the thing. It was for show. And, my roommate was part of the problem. You see, he loved going out to eat as much as I did. We both hated cooking. We were both single. We had good jobs in the IT industry, so we had money to spend.

And, we chose to spend it on food. We never ate breakfast, but had lunch and dinner out every single day of the week. $150 to $200 a week, gone.

I also packed on a good 50 pounds by the time I moved across the country to Arizona and started living by myself (about five years into my career). I weighed in at at least 250 pounds after all those years of eating caloric, but oh-so-tasty, restaurant food. Pictures of me at that time weren’t pretty!

What I learned: I love to eat out, but eating out – at least as much as I once had – is a horrible spending choice. As much as I hate to cook (and I DO hate to cook), that needs to be my primary source of meals, not running up to Chipotle or Chilis every time I get hungry.

I expected things to happen TO me

This was my most devastating failure and one that I’ve always regretted. As a young lad, I had certain expectations that if you acted a certain way, or said certain words, that certain things would happen as a result. Cause and effect.

A simple mathematical equation.

But, life doesn’t work that way. Life isn’t a set of equations. Life is organic. Sometimes, shit happens whether you expected or deserved it or not. Bad things happen to good people. Good things happen to bad people. Math does an amazing job at balancing a checkbook, but it doesn’t magically explain life. Sometimes, 1 + 1 doesn’t equal 2.

When it comes to figuring out life, there are just too many variables in the mix to simplify things to that degree.

We need to make things happen FOR us – rather than expect things to happen TO us. I thought asking for help was a sign of weakness. I thought anyone who spoke over me was guilty of a deliberate sabotage of me personally. Everything that didn’t happen exactly as I expected them to was somehow “overcome by events” and not my fault.

The more life I lived, the more I learned that life WILL happen to us if we aren’t proactive. We have a hell of a lot more control over our lives than we care to admit. The choices we make each and every day help shape the next day. And the next. Everything adds up. The pile gets deeper.

What I learned: The more proactive I am, the more successful I become. I am not afraid to ask for help. I no longer take things so personally. People are going to be who they want to be, and that includes me. I finally asked myself who that person is. Who do I want to be? Then, be that person.

Money means very little without purpose

Straight out of college, I made good money. It was my very first real gig, and I was enjoying the cash flow. And let’s be honest: This is natural. The first time a person makes real money, they’ll spend it.

Finally. Dependable spendable cash!

But, it’s not like I didn’t save at all. I saved a little.

I did what I thought I was supposed to do regarding that “saving” thing. I contributed just enough into my 401k so the company would match it. I put a few pennies each month into a company-sponsored Roth IRA as well. I also budgeted. Each and every paycheck, I’d fan out that money into their respective pots, then proceed about my life as if everything was fine.

Truth be told, things were fine…so long as I had no intention of retiring anytime soon. My budget was failing me (or rather, I was failing my budget).

Worse of all, I had absolutely no idea.

I robotically budgeted, but it was purely circumstantial. Beyond the pittance I saved into my 401k and my “reserve” pot from my budget, I basically considered everything else to be freely available money for spending.

Not money that COULD be spent. Money that SHOULD be spent.

And like a good little soldier, I spent it. Spent it good. Spent it on nice things, like expensive camera equipment. A miniature pool table for my already-crowded little apartment. Restaurants. Anything I wanted, I bought.

My money didn’t have a purpose. I “saved” like I thought I should and then proceeded to spend the rest simply because I could.

It’s like chocolate lying on your bedside table. I mean, come on! That chocolate is there to be eaten, not stared at and saved for later. It’s right there! You’re doing well. You’re working hard. You deserve to have a piece.

What I learned: Budgeting isn’t the magic sauce to financial independence and early retirement. Neither is saving. Money needs a purpose. A reason for its presence. Simply “having money” doesn’t get people rich, and it sure as hell won’t let any of us retire early. Not without a purpose.

However, on the bright side…

I’ve made a lot of mistakes. And, that’s okay. I made these retirement-killing errors while I was young and with a lot of time to correct them. In a way, I think I got them completely out of my system.

In theory, I won’t make those same mistakes again. In theory…

For example:

I know what driving around in a loud sports car and the fastest bike on the road is like, so I no longer have that urge.

I know what it’s like to eat every meal out and live like a rockstar.

I’ve been the person who buys himself everything he wants, almost without hesitation. Been there, done that.

Throughout all these mistakes, the urge to live like a badass superstar has come and gone. Hopefully, for good.

But, I keep asking myself: If I hadn’t made those mistakes in a previous life, would I be more likely to make them in a later one?

P.S. Check out the chain gang of other personal finance bloggers who are writing about their mistakes in life and what they learned from them!

ThinkSaveRetire – Don’t brag about success; tell me your failures

A Chronical of a Father with Cents – My financial mistakes

A Journey to FI – My financial mistakes

OthalaFehu – Budget Bungles, Money Muddles, and Fiscal Flubs

Turning Point Money – My Financial Mistakes

Femme Cents – 7 Lessons I Learned from my Biggest Financial Mistake

Jumpstart From Scratch – Recent financial blunder

Gen Y Money – Investing mistakes in my 20s

Atypical Life – Five super lame blunders from my life

The Frugal Gene – Top 5 sorry ass mistakes made in my 20s

99 to 1 percent – 6 financial mistakes and 15 lessons learned

Winning Personal Finance – My 7 most regrettable financial decisions

Chief Mom Officer – Overdrawn checking account!

Foreign Born MD – Biggest mistake: Over a million dollars worth

Join the Newsletter

Fork over your email to get articles on building a kick-ass mindset, saving money, early retirement, financial freedom and living life to the fullest - sent straight to your inbox.

No-spam guarantee. Unsubscribe at any time. Powered by ConvertKit