3 Embarrassing Investing Mistakes I Made in My 30s I Wish I Never Did

Oh! My lost money…

I wished I had never made these mistakes. Really.

It was an embarrassment. Total facepalm. And I wish it was as simple as losing some money.

But no. It was a toxic combination of the following.

• Losing big money,
• Making investments that I shouldn’t,
• [Blindly] Following the footsteps of the Greats when I do not have their financial war chest.

I was humbled.

But I learned.

Now, I think twice. After all, I am deploying my hard-earned money. I don’t want to lose it to silly mistakes.

Losing Big Money

This is the thing.

No one has the intention to lose big money from the Get-Go.

It starts with a simple intention to make big money. We all do. We think making big money faster solves that I-hate-my-life-and-job problem.

If you have this thinking as I did, then…

Firstly, you are going to lose big money fast.

Reason? You will [always] be throwing money on the Bright Shining Objects near the market top. We know what happens shortly after. Yup, that is how we get killed.

Secondly, money cannot solve problems related to our existential crisis.

We must know what we want in life. Otherwise, we are [just] one floating log in the human ocean bumping against another drifting log.

That was me.

When I started investing, I thought it would help me be happy with myself. It didn’t. The opposite happened.

I lost 75% of my money investing in telecommunications companies in 2014 and 2015. I saw their price line skyrocketing to the moon. I wanted to hitch a ride on the way up.

I did.

But it did not go up. The ride crashed back to Earth.

So, don’t.

Don’t do this.

Go steady. Be prudent at the start line. Pick investments you know. Invest with small sums. Increase your quantum over time.

Grow your confidence as an investor.

You will stay on the course for longer.

Making Investments I Shouldn’t Have

Well.

Reflecting on this mistake turns my face into a hot tomato. I mean it.

It’s burning.

Like now.

As I type.

There are investments that we don’t understand. Of course. No one, absolutely no one, can have a comprehensive grasp of the investment world.

It is too vast and diverse.

You may,

• Understand equity investing in the public space and have no clue about private equity,
• Invest in treasuries and corporate bonds but do not understand distressed debt,
• Amass gold and silver to hold your wealth and lose money on platinum.

If this strikes a chord with you… take heart.

Things happen. We learn.

I used to allocate some money to private equity investments. Then, I sought control of the business that public investments do not offer.

[Retail] Apple shareholders do not sit in the boardroom to partake in boardroom discussions, right? We cannot veto. They tell us. We listen.

It annoyed me.

And so, I had this weird thought. I thought [I sincerely did] that I could earn more in the share of profits if I had a say in the business.

Well.

I was wrong. Dead wrong.

The café business I invested in was a mess. The entrepreneur is a barista by training. He needed funds to keep the café going.

But.

• He is financially illiterate.
• And he is a sucker for quality beans.
• He would make a cup of connoisseur-grade coffee for $20 and sell it for $7.

What. The. F.

My investment money in this café burned down to the last dollar with $0 returns.

We part ways after multiple shouting matches. Face-to-face. Online.

In retrospect, I have bitten more than I could chew.

I should have understood the mechanics of business better before making the jump. I should have. Sigh.

Following the Greats [Blindly]

This is another facepalm.

*Sigh*

I am an investment content junkie. I could listen to Ken Griffin, Warren Buffett, Mark Howards, Robert Kiyosaki. and Ray Dalio on YouTube all day.

And then, I would follow in their footsteps.

Blindly. Religiously.

It never crossed my mind that we are different. Stupid me thought I could do [exactly] what these Titans could.

“If they can do it, so can I.”

It is the [exact] kind of rubbish online self-improvement junkies feed you.

I am here to put this idea to rest.

No, you cannot.

Here’s why.

It takes experience, confidence, and a boat of failures to get to where they are today. Their investment paradigms are a result of years and years of experience. We cannot cut it short.

Take Rich Dad.

Robert’s investment philosophy hinges on the following.

• Major currencies lose value and purchasing power steadily over time.
• Using debt to acquire assets is the fast track to financial freedom.
• Buying gold and silver to hold wealth.

We cannot do what he is doing right now.

Not when you are broke. Banks won’t lend you money.

And debt can eat you alive if you are not careful. It is a weapon. It can blow up. Many people I know are struggling with their credit card debt. They should avoid Robert’s teachings.

They may learn the wrong lessons.

For me, I fully endorse Robert’s lessons. Philosophically, he is right on point, especially on the currencies part. He got me worried about my cash.

And so, I over-invested myself. I left very little cash for my day-to-day.

Guess what happened?

A dental operation almost wiped me out. Stupid, I am.

Today, I no longer do that.

I am not as rich as Rich Dad. I must hold back and keep some cash in the bank for emergencies.

I learned.

The Close

Yes, I am embarrassed.

I made many stupid mistakes in my investment experience.

In fact, they are so stupid that I…

… I cannot help but sigh as I type.

You see… we always imagine we can do what the Greats do. Yes, we can. But not today. Or tomorrow.

We need time to practice, to figure out the booby traps, to learn from our mistakes.

It takes years, not weeks.

It is way better to start small, be prudent, get involved, and increase our investment money steadily over time.

• Yes. We don’t make big money.
• But no. We don’t lose big money.

And I think that matters.

Right?

Right.

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