10 Reasons You Should Quit Your Day Job But Not Your Day Dream


Mostly, I was a criminal.

Unless I was excited, I could care less. And I’d actively sabotage my job and my happiness.

I eat what I kill. The magic happens only when I’m in love.

Ten things I learned while I quit all my day jobs and made money from my day dreams.

1. Income will make you poor

There’s two reasons income will make you poor.

A) As soon as you get it, you give it.

40% goes to taxes. So always you are 40% a government employee. Is that what you dreamed of being?

And then what happens to the rest?

Another 30% goes to living costs. And then, if you have kids and responsibilities, another 30 to 40% goes to keeping them alive.

Nothing left.

B) Your income is only a fraction of your value

When I had a job, I had a boss, who had a boss, who had a boss, who had a boss, who had a boss, who had a boss, who had a boss. And then his boss were the shareholders of Time Warner.

I created the value. But every boss above me had to take money out of that value in order to feed themselves.

This is how corporatism (but not capitalism) works. It’s a feudal system justified by bad economists.

In the value you create, you probably keep about 5% of that value.

How do I know it’s only 5%?

Because I know how much more money I made when I quit my job and was able to keep a lot more of the value I created.

2. Choose the people you want to be with

I love my friends. I actually love them. I enjoy being around them. Seeing them. Working with them.

When someone I work with causes me a personal issue, I stop working with them. I stop being their friend. I’m not ruthless. They have to do something very bad.

You need to eat good food for the body to live.

The people you are around are the food for your heart.

This is not selfish. You can only be around the people you love if you prove yourself loveable.

Why is this in an article about jobs? Because when I work at a job I don’t get to choose who I am around.

If the people you love don’t intersect heavily the people you work with, then you have to be in a different place in life.

3. More choices

I grew up in a suburb of New York City. It was a middle class suburb.

Which means everyone was middle management in NYC and commuted every day to NYC. Everyone was a “VP of Sales” at an accounting firm.

Around age 50 they all had their first heart attacks. Then strokes. Then cancer. Then some dementia. Then death.

Now, we have choices. A friend of mine spent 20 years working for Wall Street as a graphic designer. Finally she quit.

Since then she’s been inundated on every social media site for requests to do work at some times triple the money.

Why? Because now she posts art and graphics that she makes out of love. She creates her day dreams, the ones she’s had since she was a little girl.

People see them and say, “I want that energy in my life!” and they offer her money to do it.

She also took out the middleman – headhunters, design agencies, HR people, bosses, etc.

Let’s say I want to publish a book. I can’t do it unless: agent, editorial assistant, editor, marketer, publisher, bookstore purchaser, all agree that the book should be published.

Unless I just write the book and upload it to Amazon.

In every industry now you have choices of how you can make more money.

How can you get started? Hold on…

4. All industries are dying

Nobody makes a “buggy” for a horse anymore. That skill set is no longer in demand.

Nobody wakes up and says, “I’m going to make a chain of stores to sell music CDs.” That industry died also – not 100 years ago but 10 years ago.

I don’t need to give a lawyer $10,000 to start a company. I can spend $100 on LegalZoom. I don’t need to hire a designer for $20,000 to build a website. I can do it for $1000 on 99Designs.

I don’t even need a doctor to operate on me. In many cases, robots are more precise and saving more lives.

This doesn’t mean all industries are dead!

All people are dying. But they aren’t all dead. Yet.

Find the young industries where you can make a difference. This is where all the money falls by force of economic gravity.

But most industries, the ones that employ 100 million people in the United States, are walking dead.

By 2020, half of all jobs will be freelance. That is the direction society is going in.

5. You are using 100% of your brain but 1% of your potential

There used to be a cliche: “We only use 5% of our brain”.

This is not true. We are always using 100% of our brain. Else our brain would not have evolved.

The parts of our brain that we didn’t use would have atrophied and not been passed down in our genes.

BUT…we do only use 1% of our brain’s potential.

If you are in a coma for two weeks, you won’t be able to stand up and walk. The leg muscles atrophy.

Creativity is a muscle also. When I had a full time job (or even a business that was going bad) that I was not super excited about, I would not use my full creativity. In fact, I’d get bored.

My creativity muscle would atrophy.

Creativity gets replaced with: complaining,. unhappiness, anger (“I can’t believe my boss said that!”), and excuses (“I can’t leave my job because…”) .

It’s hard to quit your job tomorrow. Don’t do that.

  • But do one creative thing a day.
  • Take a beautiful photo every day and write a story about it.
  • or journal every day.
  • or paint.
  • or make people laugh. Or … watch things that make you laugh.
  • or get good at a game. To win a game you have to be more creative than the other person.

Then you can get your creative muscles strong. 99.9% of people aren’t doing this. Once you start doing this you will see what I mean.

The other creatives will stand out. Everyone else will look blurry and sad.

It’s like there was a morning fog that made you feel lethargic before. And now the fog has lifted.

6. What zone are you in?

There’s the COUCH ZONE (“I like to eat popcorn all day and sleep”). There’s the SAFETY ZONE (“I’m going to work my steady job, hope I don’t get fired, and retire and try to enjoy the remaining years of my life”).

There’s the COMFORT ZONE (“I have to make a paycheck and own a house but I’m not going to go off on my own. Too much risk.”)

There’s the DISCOMFORT ZONE (“I’m going to make a new friend every day.”)

There’s the DANGER ZONE (“I’m quitting my job and exploring my dreams! I have no idea what I will do tomorrow but I can’t take another day of this”)

Then there’s the “FREE ZONE”, (“I’m going to keep experimenting and ultimately scale the things that work.”)

All the zones are fine.

Sometimes I’m in the couch zone. I don’t mind. It’s ok to sleep on the couch. But i try to spend as much time as I can in the free zone.

The civilians are stuck in the comfort zone. This is ok also. But they might not see all the things that are happening around them that make the Free Zone so beautiful.

The Secret Agents in our society use creativity to track down where the Free Zone is. This is where I want to be.

7. Money happens when you combine your day dream with your day

Money is not the goal. But I know that I need it to live. No matter what, I need money.

I used to say, “one of these days I’ll pursue my daydreams”.

But my day job was never over and my day dreams would atrophy.

When I finally combined my interests in entertainment with software, I was able to start my first company.

When I combined my interests in games, software, and finance, I was able to start my first hedge fund.

When I combined my interests in website development with investing, I was able to start another company which I successfully sold.

Or I look at my podcast guests over the years.

Matt Berry left his INCREDIBLE job of writing movies to pursue his real interest. Fantasy sports. He started blogging for only $100 a post.

Years later he’s now the ESPN Anchor for Fantasy Sports. He runs several companies.

Last time we went to lunch together people were coming up to the table and thanking him. He was smiling the whole time. “I love what I do,” he told me.

Or Brian Koppelman was an entertainment lawyer in the music business. He was miserable.

So every night he played poker, which he loved. And he spent every early morning learning how to write a script with his friend David Levien.

Then they wrote the hit movie “Rounders” starring Matt Damon as a poker player.

Or Tim Ferriss was working on a nutraceutical company, BrainQuicken. He was working 100 hours a week and hated it.

So he started to figure out how to work less hours, but get almost the same value.

He started documenting the process of what he was doing. His blog about how he was reducing his hours while becoming more productive became a hit.

Then his book, “The 4 Hour Workweek” started him on a completely new career.

It takes years. But it works.

Creativity wants to come out in play if you feed it just a little bit every day.

8. Deflation of income but there is inflation of all the assets we need

If you are ages 18-35, you’re having a big problem.

Since 1992, average income for that group has gone from $36,000 to $33,000. Income is going down.

But there’s an even worse problem:

Healthcare costs are more expensive than ever and go up every year.

Housing costs have gone up.

Education costs go up every year.

And even basics like food and clothing go up every year.

If income goes down while assets go up it can only mean one thing: everyone will get crushed in the middle.

The only way out of it is to see “B” above and get more cash out of the value you create.

I dated someone once who said, “Money is your religion”.

It’s not. In fact, I don’t want or own any possessions except what I can fit into one single bag.

If I buy anything, even a t-shirt, I have to throw something out so it can fit in my bag.

But I have two kids. So I have to pay for their needs. I have responsibilities that cost money. Else, I’d just as soon live in a homeless shelter and not care.

Money is the payoff on SOMEONE’s creative efforts. Be the someone.

9. Love

One third of workplace romances end up in marriage.

So you want to work with people you are most likely to truly love. if you are put in a position where you can’t choose the people you work with, it’s no wonder of the high divorce rate.

Work with people you love, so you can love the people you marry. Then have happy babies.

10. What can you do?

I had a lot of daydreams as a kid. I wanted to be a writer. I wanted to interview people. I wanted to call up my heroes and talk to them.

I also wanted to be an astronaut. Be president. Be a football player. And be an eccentric billionaire who peed in jars and had super long fingernails.

Some daydreams come true and some don’t. But I still have lots of daydreams.

I want to write a novel. I want to continue calling my heroes and interview them. I want to make people laugh. I want to help a lot of people. I want to write every day.

These things excite me.

I write down my daydreams all of the time. Then I write down my 10 ideas of the day. “10 ways I can be an astronaut”. “10 ways I can help Amazon”. Etc.

Combine your daydreams. “10 ways I can write about astronauts”.” Or…”ten ways I can make money writing about games I like to play.”

Here’s the plan:

  • What are your day dreams?
  • Write them down
  • Combine them
  • Write down ten “10 ways I can start being X” where X is the daydream or the combination of dreams.
  • Take the first tiny step.
  • Repeat

We are constantly in a state of reinvention. We have to be. You can’t step in the same river twice. That’s why “repeat” is important.

Most things won’t work. And most things will end up in the excuse zone (“that will never work because…”) .

You only have to work on the daydream for a tiny bit each day. That’s all it takes. 1% per day compounds to 3800% per year.

Working on making a day dream come true, even a tiny bit, makes me feel like my hands were put to good use today.

Else…what’s the point?

As Jewel told me in our podcast, “Watch what your hands do…they will tell you who you are.”

At the end of a day, I want to go to sleep with that good kind of tired. Sore but happy.

I want to wake up. Excited for the day. Living the dream.