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This Is What It Feels like to Lose a Stupid Amount of Money

by | Dec 21, 2021 | Money

Losing a lot of money makes me smile.

My friends think I’m a money psychopath because of it. The few times it’s happened, I’m in tears and going through tissues faster than toilet paper after a spicy curry. About 48 hours later I manage to smile and get back up.

When I walked away from a business I loved (and a lot of money) the first time, it felt like the end. 

I pictured myself staying with my grandma for free, then my aunty after grandma died. I dreamt of sitting at home each day and watching daytime tv, like “The Golden Girls” or reruns of Tim Allen in “Home Improvement.”

Now that I look back, what felt like the end was actually the beginning of the best time of my life.

Here’s what financial loss has taught me.

You’re in the game. Congrats.

Life is a game. Losing money means you’re putting yourself out there. You’re trying shi*t on to see what sticks.

It’s better to be in the game than live in fear and sit on the sidelines in comfort. In comfort, you get pulled down by what-ifs and “how do I get what I want?” All the questions you have about life come from doing, not thinking about what might be possible.

Like with any game, there are risks. You’ve gotta risk it for the biscuit. Don’t let the thought of losing money stop you from living.

Here’s why…

Major financial loss is guaranteed once in your life

Let’s not pretend it isn’t true.

When you make money your levels of ego and risk fluctuate.

With more money you care less, and that’s where financial mistakes can happen. Your guard can get let down. That makes way for no-good half-wits to let themselves in and perhaps help themselves to some of your cashola.

But if you learn to accept financial losses will happen, it’s possible to see the good before the bad occurs.

How major financial losses happen to all of us

You can build something big and beautiful over many years. It can all get ripped down overnight. The question is, how?

A few bad decisions. That’s all it takes.

Decisions shape your life. When you’ve done okay financially the mood you’re in can shift. You can pay less attention to the tiny details of financial decisions you make.

The trick is, allocate time and patience to financial decisions. Don’t act like a fool and throw cash around because now you have some.

Keep humble, keep your money

Lifestyle creep makes us ungrateful as we earn more money later in our careers. The things we used to dream of now don’t have the same shine.

Our tastes begin to get more devine. We can start to think that we deserve certain things or should get treated in a certain way (often better than others).

There’s one tool that has saved my life.

It sounds woo-woo and like it’s the advice a fairy godmother would give you. But it’s true and corporate giants that bleed your wallet dry don’t want you to know this secret.

Write down three things you’re grateful for every day.

That’s it.

When you do that you realize how much you already have, so you don’t let money screw with your beautiful brain.

The bizarre financial times will catch up with you

Interest rates are at 0%. You get nothing on your savings. I told this to my friend’s 5th grader daughter. “Which way are interest rates going?”


Doesn’t take a genius to see the risk building up in the financial system.

Will there be another 2008 style recession? Will the next one be bigger? Will overpriced real estate crash?

Will another coroni-macaroni leak out of a wet market and into the blood of humans again for round two? Or will a climate curveball come from nowhere and change the way earth is forever? Or will a bank fail because they took too much risk?

Nobody knows. I’m not your guru.

What I know for sure is, no one can predict it. It will come out of nowhere and take people by surprise, like our mate coroni. It will be too late to react by that point, and many innocent people will lose most or even all of their money.

That’s the nature of the financial beast. Even the smartest people in 2008 got smashed in the face with a brick, thanks to an innocent financial product known as derivatives. When you become aware of how unpredictable recessions can be, it changes how you approach money.

Your obsession with earning money can change.

The nothingness of money will throw a spanner in your brain

An article called “The Nothingness of Money” helps put inevitable financial loss into perspective. In it the author dissects our thoughts about money over our lifetime.

As a baby, your thoughts about money are zero. As a child you realize money can buy you lollipops. As a teenager you realize your parents’ hot water isn’t infinitely free. As an adult you realize you’ll starve and become homeless if you don’t earn money. On your final day before death, money seems stupid. You can’t eat it and have it come with you to the afterlife.

There’s a brick wall between the stuff money buys, and what you take to the next life. The closer you are to that brick wall, the more stupid money seems.

Imagine the doctors told you that tomorrow is the day you will die from an illness. You wouldn’t jump in your car to work another shift and collect money. It would seem stupid and pointless.

Here’s the problem: 

You don’t know when you’re going to die, so until then you have to care about money and let it occupy space in your brain.

The nothingness of money is only realized when your death becomes known. That’s when your thoughts about money die.

The modern design of work built this reality in. The retirement age of 65 is meant to decrease our thoughts about money as we get closer to death. Work hard while you’re young, so you can think about money less when you’re old.

The author of the nothingness article goes on to explain that the FIRE (retire early) movement tries to fix the problem. The idea with FIRE is you focus heavily on money from early adulthood to your late 30s. Then you can relax. The FIRE lifestyle design increases the thoughts you have about money.

You can’t even drink a Starbucks cappuccino without feeling guilty.

Even after you have enough money these elevated thoughts about it — that you need to have to be part of the retire early crowd — stick with you. It’s hard to undo the programming. So money works against you.

The article finishes with the fact that all wisdom about money is contradictory. The author explains that you’re not going to get your stock portfolio printed on your tombstone, therefore, it’s best to laugh at the nothingness of money right now … instead of later.

Apply the nothingness of money to financial loss. It heals all wounds.

An ending to leave you inspired

Every time in my life when I’ve lost a lot of money, I’ve come back twice as strong. The people I know who’ve gone bankrupt are perfect examples of this reality. Financial loss rebuilds their lives in new and beautiful ways.

The failed business becomes the blueprint of what not to do. A stock market crash reveals the power of risk. A crypto bear market shows the humble side of some of the cockiest people on the planet.

Here’s a final summary of what I’ve learned:

  • The money you will lose gives you fuel to grow.
  • Your convictions about investing in certain assets will become stronger.
  • A financial loss can help you avoid catastrophes you will never become aware of.
  • A financial loss ruins most people. If you survive it you’ll make your future self proud.
  • Bizarrely, when you lose money you feel happier — because the nothingness of money comes to life.

The losses create the eventual wins.

This article is for informational purposes only, it should not be considered financial, tax or legal advice. Consult a financial professional before making any major financial decisions.

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