11 Reasons You HAVE to Quit Your Job in 2019

I did a bad thing.

I was in the middle of a meeting. It was my second week at a new job. I had set up the meeting with some people I thought we could do business with.

Suddenly I couldn’t bare the thought of spending another second at that job. For all the reasons I list below and maybe some more.

I hated it. I couldn’t stand the sound of my voice. I hated the people around me. I was dying.

I had my coat hanging on my chair and another coat in my office. My office already had my name on the door. This was my first attempt at a real job in about 15 years.

I said, “I have to go to the bathroom”.

I got up. I left my coats behind.

I limped toward the lobby because I had fallen the day before for reasons I still don’t understand. I was going in the opposite direction of the bathroom.

I said goodbye to the receptionist. I hit the “L” on the elevator. I rode all the way down the Trump Building on 40 Wall Street.

I took the 1 train to Grand Central, got on a train, went 60 miles north of NYC, and went home.

I never went back to that job. I never spoke to anyone there again. The main guy called, emailed, begged, asked what happened, offered to negotiate more salary, offered anything I wanted.

I never responded. Never spoke to him again. I feel bad about that. I’m a pretty non-confrontational person and I’ve had to work on that.

I had no job, I was starting to once again run low on money, I had no prospects.

But I’m so glad I quit!

That year, all of life opened up to me. So many opportunities. So many ideas that I started to explore. Some worked. Some didn’t. But I learned from all of them.

And, since then, each year has been more successful than the last.



People used to get a job for the stability. My grandfather started his job in 1946 and retired with a gold watch in the 1970s.

But as Nassim Taleb suggests, “the three biggest addictions are heroin, carbs, and a stable paycheck”.

Companies are not loyal. They don’t care about you or me.

But that’s OK.

We live in “The Access Economy”. Every access economy company has three components but many ways to benefit:

  • EXCESS: Some people have excess of X. E.g. excess empty car seats, excess apartment space, excess time to do tasks, excess knowledge, etc.
  • DESIRE: Some people have great desire for that excess. E.g. some people want access to empty car seats when they can’t find a cab. Some people want access to empty apartments rather than a hotel.
  • PLATFORM: To connect “A” and “B”, to provide search, to provide secure transactions, to mediate difficulties, to provide reviews and standards.

Uber, Airbnb, TaskRabbit, Seamless, Freelancer, Fiverr, etc. are all examples of Access Economy companies.

You can make money by owning the platform. Or by providing the excess. Or by providing services to the excess (e.g. an “Airbnb manager” who helps multiple hosts manage their Airbnb listings and services).

You can also provide excess knowledge about a topic (e.g. dieting) to people who would like that excess knowledge and are willing to pay for it. You can use platforms such as Facebook, Amazon, or even Kickstarter or Etsy (depending on the knowledge or the product) as your distribution platform.

This is just one way of looking at the “Gig Economy” but there are others.

The gig economy is growing every year. Can you replace your income from it?

I did it. Although I did it when it was almost impossible. In 1995 I had a full-time job. But I started making websites for companies on the side.


TAKE BABY STEPS. Always take the temperature of what side hustles are out there, what your value is in the job market, what gigs you enjoy, how much money you can make, how you can grow.

By 1997 I was doing well enough with my side hustle that I left my corporate job and started doing it full time.

Then I scaled it into a business and eventually sold the business.

SJ Scott writes books about habits and self-publishes them on Amazon. When he started he was depressed, doing nothing, and sleeping on a couch.

Now he makes up to $60,000 a month.

Hannah Dixon makes a full income as a virtual assistant while she travels around the world and writes about her experiences.

One friend of mine quit his job, wrote a diet newsletter called “What Would Jesus Eat” (essentially… a Mediterranean diet) and now lives in a three-story penthouse in Medellin.

The list of people I’ve spoken to who have left their jobs forever for “gig economy” jobs is enormous. And there are more every year.

Here’s a chart I put together on “how to make $2,000 in a weekend”.

If you are an “animator” by training, please don’t be offended. I’m not suggesting someone can make “Toy Story IV” in their spare time.

But there are courses on Khan Academy, CodeAcademy, Lynda, and elsewhere that give cheap or free courses for almost any skill that can be used to make $2,000 in a weekend.

Start small. Start easy. Don’t get stressed about “building a business”. Learn the skills, get one client, scale, repeat.


Nobody can get rich from a job. You can’t build real abundance.

According to the IRS, the average millionaire has seven sources of income.

This is important for two reasons:

  • A job is only ONE source of income. But if it’s taking fifty hours a week (40 hours plus commuting, etc.) you won’t have time for other sources.
  • Even more interesting: BEING AN ENTREPRENEUR is only one source of income.

If you want to be an entrepreneur, go for it.

You have a vision, you have a client, you have business sense, you have profits (so you don’t need welfare from vulture capital firms), and you have a sense of how you can sell your company.

But you can be a “lifestyle entrepreneur” as well. Focus on skill acquisition and providing services (or finding a good side hustle) that you can decide to either scale or move onto the next stream of income.

Another side hustle I like: find stuff cheap on Ali Baba. Sell expensive on Amazon.

But this isn’t an article on being an entrepreneur.

I’m so glad I quit my job when I did. I’ve done it twice in my life. Both times changed my life.


At least… my very first boss hated me. The only way I could keep doing what I wanted when I had a job was to keep giving him credit for everything I did.

Else he’d call me into his office and yell at me. I don’t think any adult should be yelled at by another adult.

If you hate your job, so does your boss.


Because he’s in the same spot you are. He’s got a boss, who has a boss, who has a boss, who has a boss.

Unless you are working for an entrepreneurial company where you are learning huge skills and maybe its even paying you in proportion to the value you bring, then you are often at the narcissistic whims of your boss.

79% of people who leave their jobs cite “lack of appreciation” a.k.a. their boss hates them.

And he or she is struggling to hold onto their job as well, while all the young people are learning new skills, working longer hours, and have less responsibilities at home.

They are afraid of you. They will block you from success and happiness.

And will throw you under the bus if they need to in order to save their own temporary status in the middle class.


Here’s average income since 1990 for people ages 25–34:

Note it hasn’t changed. This sucks.

How come? Because student loan debt for that age group has gone from near $0 to over a trillion dollars.

Because health care costs have gone up 8x faster than inflation.

Because job turnover is greater than ever so there is more uncertainty.

Salary is the same BUT health care is up HUGE and loans are up HUGE = DISAPPEARING MIDDLE CLASS.

1991 is when “the web” began it’s non-stop rise into the mainstream, increasing productivity, costing jobs, reducing the need for middle management and other middle class jobs.

What’s next? AI, robots, blockchain, and the access economy described above will further reduce the need for middle class positions.

What’s next? 20 million young Americans with student loan debt will be forced to take jobs they hate because they can’t get rid of this debt in bankruptcy.

Because they are forced to starting paying down these loans, corporations will know they have a serf-like audience of potential employees and will pay less and less money.

These 20 million people who might have once been innovators or started companies or took more risks are now forced to be salesmen in eyeglass stores just to make interest payments and pay rent.

Nothing wrong with that job. But they can never leave that job. Dooming them to leave the middle class their parents enjoyed in the ’70s through the ’90s and forcing them to cut every corner.

The middle class is dying and nobody cares.


Here’s how I like to make a “YES” decision:

  • Will the “YES” improve my relationships with others?
  • Will the “YES” improve my mastery of something I love?
  • Will the “YES” increase my freedom – my ability to make more decisions for myself each day?

At a job, you are forced to be friends with people simply if they are in the cubicle next to you.

At a job, skill acquisition is limited to the particular micro-niche your company has assigned you to.

At a job, you have rules about what to wear, how to speak to the opposite sex, what time to come into work, what activity you have to do for 50 weeks of each year, and even what you are allowed to take home. (Don’t steal the paperclips!)

A job will hardly meet the qualifications above. And those qualifications are the three components of what positive psychologists call “well-being”.

In other words, a job equals unwell-being.


When I worked for a big company there was great healthcare, four weeks vacation, and you basically could get away with hanging out doing nothing most of the day.

Right now, according to a study by Glassdoor, the average employee sacrificed over 50% of their vacation last year. And 10% of employees took none of their vacation time.

How come? Because they won’t want to be replaced by the other people who are taking no vacation time.

40 years of that and you are dead and what was it all for?

Well, what about the benefits of stability that jobs supposedly had?


Two out of five employees in America blame gaining weight on their jobs.

They are sitting around all day, snacking, and too busy to take advantage of the wellness programs offered by their employers (63% say they don’t use any of the wellness programs of their employers).

Spending on healthcare by employees WHO ARE COVERED by health insurance increased 44% between 2006 and now according to the Healthcare Cost Institute.


I have no idea. All I know is the end result. A job is costing people more money on their medical spending.

A job is costing people less health.


I was jealous when my friend got promoted to “Senior Programmer Analyst”.

I was a “Junior Programmer Analyst” and I thought I was better than him. But he had been there longer.

And then after that was “assistant project manager”, “project manager”, “director”, “vice president”, “senior vice president”, and then a bunch of other titles.

Everyone had a rank. Like in the military.

And everyone had to pay respect to people higher in the ranking system.

This sucks. We’re not monkeys. But we are.

Every species of primate fires off neurochemicals depending on whether they are moving up or down the hierarchy of the tribe.

The main benefit of being human is that we can be in more than one tribe. We can diversify our status hierarchies.

Money might be one hierarchy.

Many people think net worth leads to more self-worth. I know for me I was dead broke when I finally realized that self-worth leads to more net worth.

But also golf score can be another status hierarchy. Or “likes” on Instagram. Or reviews on a creative project. Or skills acquired at an online learning site.

At a job, there is one hierarchy. Just like in a tribe of monkeys. But when you leave the job, you can pick and choose hierarchies.

Whenever I am feeling down about one area of my life, I focus on the areas of my life where I can improve, feel better about my status, and re-energize accordingly.

“Happy brain chemicals” like serotonin, dopamine (the leading causes of depression when they are lacking), and oxytocin are all related to where you fit into your hierarchy.

The way to not be a monkey and have more opportunities to increase your happy chemicals is to be in more than one tribe.

I used to daytrade. Day trading often is horrible.

You can lose money and every neurochemical is going the wrong way. But because I wasn’t working 40 hours a week, I had time to exercise (increasing endorphins, improving my stamina, etc.).

I had time for creative projects (another status hierarchy) or I could simply play chess more (improving my ranking in that world).

Diversification is not an “invest in stocks” strategy. It’s an “invest in happiness” strategy. One that is harder when you have a full time job.


Most eight hour jobs mean you work two hours a day TOPS and then sit around in meetings, chatting with co-workers you don’t like, taking coffee breaks, commuting, doing nothing.

This is what a typical work day is like:

Wake up at 6am, eat, commute, work by 9am. Then there’s smoking breaks, eating breaks, coffee breaks, commute.

Actual work involves meetings. How many hours per day? I don’t know.

When I was at a corporate job I suspect the average person actually was working about 10 of the 40 hour work week and mostly wasting time the other 30 hours.

30 hours a week for 50 weeks is 1,500 hours.

I wanted those 1,500 hours.

Build a business, write a book, learn new skills, be with family, play games, whatever you want.

Being productive is not about sitting behind a desk so you get a promotion.

Being productive is about using time to make a better you.


There was ZERO chance I was going to go to the bathroom in the stall next to my boss.

I don’t know why. I just refused to go to the bathroom at work.

When you go to the bathroom at work, if there are no walls on the stalls, you’re just about two inches from your boss exploding the bathroom right alongside of you.

So I would run to the elevator, run across the street, down the block, go into the New York Public Library, run down four flights of stairs into the stacks, and use the one bathroom I knew was always available and empty.

But if you don’t have a job… knock yourself out. Destroy ALL the bathrooms. Who cares?


If you love your job, stick with it. If you are working at your passion job, that’s great. I’m envious of you.

But many people don’t feel that way. Many people. And I was one of them, wanting to jump ship and figure out their lives.

Many people, and I was one of them, are on the treadmill of school, college, job, job, job, retirement, death.

I often did it very wrong. Sometimes I focused on money more than freedom. Sometimes I was envious and was in the wrong status hierarchy.

Here is Danica Patrick’s (best female professional race car driver in history) advice to me on how to find your passion. Plus I will add one more:

  • Ask yourself, How would you structure the ideal day?
  • What photos are on your phone? The thing you take the most photos of might contain a clue.
  • What makes you most energized? List everything you did this past month and then rank them by how happy you were when you were doing that activity.

These all lead to clues as to your purpose.

Let me add one more.

  • What were you most interested in at ages 12–15? How have they aged?

When I was 12 I kept a notebook on “who liked who and why” about every boy and girl in my class.

Decades later I’m a writer.


Don’t believe me. Stay with a boss that hates you.

A job that is keeping you locked on a chain around your neck, tantalizing you with incremental increases in pay and job title.

Stay in a culture that is quietly replacing the entire middle class. This is not anyone’s fault. This is the tectonic plates of economics destroying an entire suburban culture that has lasted for almost 100 years.

Until you choose yourself for success, and all that choice entails, you will be locked into the prison.

You will stare into your lover’s eyes looking for a sign that he or she loves you back. But slowly the lights will fade, the warmth of another body will grow cold, and you will go to sleep dreamless in the dark once again.

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