13 Clever Money Lessons My Pain in the Ass Boss Taught Me

Tim Denning

This guy was the devil’s uncle and he can teach you a lot.

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If the devil had an uncle then this guy would be it.

Despite the obvious leadership lessons he taught me about how not to lead humans, he taught me a lot about money. The moment he became my boss I knew it would be over quickly. Over the short time I spent working for him, I took notes of all the money lessons he imparted on me before I became the dearly departed.

The cleverest money lessons come from financially rich people who are poor in all other areas of life. Money can show you the ugly side of life which you can learn from. Here’s what the devil’s uncle taught me.

Invest in yourself above all else.

That’s why he was an ass. All the money he made from holding various senior leadership roles was invested in meat pies, beer and real estate. Not a dollar was spent on self-education.

He had the self-awareness of a 5 year old. He was emotionally unintelligent. His jokes were uncomfortable. His communication style was that of a little boy playing in a sandpit and wanting to destroy all the other children’s sandcastles.

All he would have had to do was spend some of his money on understanding himself. He had childhood trauma; it was written all over his face. He clearly had lots of romantic relationship issues over the years.

You can’t prevent tragedy, but you can learn to deal with it by investing your money in yourself.

You can be rich in one area of your life and poor in others.

He was rich in the work he did. He found a way to “step over dead bodies” (as he called it) and get financially rich off a corporate fat cat salary.

To his credit he was fairly rich in the family area of his life too and prioritized his wife and children. In the areas of friendship, health, fitness, entertainment and travel, he was incredibly poor.

When you meet a financially wealthy person, take a look at what areas of their life they had to neglect in order to get the money. It’s rare someone is a billionaire and is 10/10 in all other areas of their life.

The high-net-worth individual title isn’t impressive.

This is a title he loved to drop. He wanted everyone in the office to know that his bank deemed him to be a high-net-worth individual. This was the first time I had come across this strange version of bragging.

Your financial status is nobody’s business.

Shouting from the rooftops how much money you have is a great way to get robbed and cheated by an email from a Nigerian Prince.

It’s not how much money you have. It’s what you do with it. You can do meaningful stuff with money. This is what people remember. This is what attracts people into your life that can help take you to the highest of highs and experience a sense of joy you didn’t know existed.

Titles are for the factory worker industrial age. In the 2020s it’s all about how your work contributes to the evolution of society. The meaning of your work outweighs the money it places in your bank account.

Bank digit competitions don’t beat the Olympics.

He was a competitive son of a gun. Everything was a game with a guaranteed loser — this is how he thought about money. You were either a rich winner or a poor loser. There was no in-between.

The number of zeroes at the end of your bank balance is meaningless. You can have lots of zeroes in your bank account and sit at home alone, while battling divorce, with estranged children who never want to speak to you again, and still become incredibly unhappy.

Life isn’t a competition.

A competitive mindset works against you. Why? You can’t always be the money-making winner. At some point it will be your turn to lose. I learned that when this terrible boss fired me. I had to spend my time eating shit for a while and looking for a new job.

Replace competition with the art of collaboration.
You’ll make a lot more money.

A Porsche doesn’t make you interesting.

One day I came into the office early. We went out for coffee which was never fun. He told me a story about how he was so rich and successful and threw money at a Porsche like it was nothing.

I was supposed to be interested by his Porsche porn. It didn’t make sense. It was a piece of metal with four wheels exactly like my moderately priced Honda Civic. No matter how many times he shared his Porsche story to impress people, nobody was interested.

He ended up going back to a Toyota and never talking about cars again. You don’t need to be a slave to a luxury car and get into debt.

Stick with the Toyota.

Stay away from mortgage motivation.

The moment this boss went from sweetheart to the devil’s uncle was when he casually dropped the phrase “mortgage motivation.” I’d never heard this phrase before. He explained to me before I started hiring people that I must only choose candidates who have a mortgage.

I wasn’t familiar with this interview question. That’s when I saw his true red devil colors.

“You need to select people who have a mortgage so if we need extra revenue on a particular month we can put our fingers into their backs and drive them harder. A mortgage is a form of motivation a person can’t ignore. They either comply or they can’t pay their mortgage and their family will be disappointed with them. Their partner may even leave them.”

He then told the story of how he was going to bring across his mate from another company to help with managing. Apparently, his mate was an expert at sticking fingers into people’s backs as they made phone calls to customers.

Mortgage motivation is modern-day human slavery. Don’t fall into the trap.

  • Avoid debt if you can.
  • Take on a level of debt you can easily repay (if you must).
  • Avoid employers who promote mortgage motivation.

The best money motivation is to earn money to invest into things that give you meaning in your life (and in the lives of others).

Your job title doesn’t change your salary.

Job title circus made no sense to me. It looked as though he was getting pay rises every six months. His job title kept getting fancier. That’s when a colleague alerted me to the game: you can change your job title on LinkedIn as many times as you want, to whatever you want.

Your job title doesn’t equal the amount on your paycheck.

If you buy books then actually read them.

A financial education can make you clever with money. Finance books are a great way to learn about money — from hedge fund managers, Wall Street tycoons, CEOs, tech company founders, etc.

Every day I would come to work and see books on my boss’s desk. The books seemed to randomly change a lot. I learned that leaving books on your desk is supposed to make you look smart. What made me laugh was when I found out he hadn’t actually read any of the books. Use your money to buy books and then actually read them.

Every dollar you spend learning about money is the equivalent of roughly ten dollars you don’t have to work for in the future.

Nobody cares how many homes you’ve got.

The number of homes you have doesn’t make you rich. My bad boss had lots. The funny thing was the homes were all in terrible suburbs.

Location, location, location is what counts with property. A good property in a terrible suburb with a high crime rate won’t go up as fast as a modest property in leafy green suburb with no bank robbers.

You can have a lot of homes and still be an asshole.

The way you treat people can make you a lot more money than investing in lots of properties and treating people like human slaves.

Don’t live on a golf course.

If you live on a golf course you’re not rich. You’re stupid. Who wants golf balls hitting their house?

Who wants to give directions to a kids birthday on a golf course? Who wants to have the stripy pants club hanging around the front of your house?

My bad boss lived on a golf course. It was situated in one of the most dangerous suburbs in my hometown. He paid top dollar to live in a dangerous area and brag about golf course life. Everybody at work knew about his home because he made it a point of telling everybody. It made no sense.

You can live on a golf course but if the suburb is more dangerous than Compton California, where Snoop Dog grew up, how is that a good financial decision? It isn’t. It’s also the reason why his tin pot convertible Porsche kept getting broken into, forcing him to sell his ego on a car website for $100K.

Amenities to your home don’t make you rich. The family in the home do.

Throw wads of cash at your health.

He looked like a grandpa with grey hair, even though he wasn’t old. His eyes were devil red. The white part of his eyes was pineapple yellow. His skin looked like a shriveled up paper bag you put mushrooms in.

His beer gut would hang over his belt, where all the unreleased emotion he was too afraid to let go of was stored. The financial lesson he taught me was simple: look after yourself.

Spend money on your health.

  • Buy lots of fruit and vegetables.
  • Drink water so you flush your system.
  • Lower your alcohol consumption or give it up entirely.
  • Spend money on going to a gym or doing group exercise in the sun.

The state of your body determines your energy levels. Low energy produces angry bad bosses. You can be far more productive and make a helluva lot more money when your brain isn’t foggy.

Energy is life. Energy attracts the people to you who can help you earn a decent living, so you can stress less and work less.

Replace hate with love and you’ll be filthy stinking rich.

My bad boss was an angry grandpa with a one-way ticket to the mental hospital. His financial problem was hate.

Hate makes you poor. You seek revenge and treat others badly when you’re a hater with unresolved psychological issues. Love makes you a lot of money. People who live their life with love may not have as much money in their bank account, but love makes their life worth living.

Love conquers all — even your financial goals.

Help other people make money.

It’s way more fun. Seeing people hit their financial goals and provide for their family, thanks to your help, is one of the best feelings in the world. That’s what my bad boss inspired me to do. Every bad boss can learn to become a human again.

How much money you make depends on how committed you are to working on yourself.

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Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship www.timdenning.com

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