26 Reasons Why You Should Never Have a JOB

I used to watch this show called The Big Idea with Donny Deutsch while at University (I’m dating myself now!).

I loved the stories of people doing something creative to make more money than they ever did before. This show was a source of hope and inspiration for me as I was wanting more freedom and autonomy than I was getting while working for PricewaterhouseCoopers.

I want to do something, anything that could allow me to be my own man. Even if it was something as strange as selling bowling balls or flat screen TV wall mounts online. I didn’t care, I could be proud of myself because it was my own individual success, my own life hack that would let me stand on my own.



So through the course of many failures and years of learning a new industry I finally mastered a skill that allows me to support myself independently from a job. I could always go back and do SEO work for a company, but I don’t have to.

We grow up with this idea that having a job and particularly a good job makes you a successful smart person who is able to afford a nice lifestyle and what not.

Challenging this idea is not helped by the fact that our boomer parents had jobs and a middle class life because of it. But that gig is up and in today’s world sometimes getting a job is the riskiest thing you can do.

Have you ever considered not having a job and being self employed?
Probably not. You were brought up to go to school, go to college, and get a good job. Anything outside of that was risky and would most likely lead to you being poor and on the street. In truth though. It’s weird though, you learn how to have a job, why not learn how to not have a job too?

To be honest though:

Having a job is easier than not having a job though.


When you have a job you know where to go, what to do, and how to do it. You get a consistent reliable pay and your employer takes care of your tax burden for you too. All you have to do is your job till it’s time to go home. But anything worth doing or having is not found on the easier path.

So yes, being self employed is not for everyone. Some people need to be told what to do, others have careers they truly love and find satisfaction in. If that is you, what I mean by jobs are all the dumb jobs I’ve had since I’m the son of a brick layer (literally).


The 26 reasons why you should never have a job


So here are 26 reasons why you should never have a job, or at the very least put yourself in a situation where you can always make a lateral move. Otherwise, if you can’t negotiate and have no other options you’re an indentured servant.



1) Freedom to BE yourself and BE who you are in the world


The goal is not to make a lot of money – or to obtain some status from your job. The goal is to feel amazing about what you do for a living right now, this moment, this heartbeat. We all talk about the freedom to do what we want and live where we want as the crowing achievement of working for yourself… but as someone who is on the other side now what jumps out to me is not money or working on a beach.

It’s being able to take back my self respect. To speak the truth and do something stupid. To be who I really am, without all the pretenses and courtesies of trying to fit in somewhere. I don’t have to water down my personal quirks and traits to be something.

2) Freedom to choose who is apart of your life


Most think not having a job gives more freedom. It does, but it’s a different, wonderful type of freedom. It’s the kind of freedom to be able to choose who is apart of your life and who is not. I can think of nothing more satisfying than not having to deal with people you don’t like.

Every place I have ever worked there was always one person that did not like me for no particular reason, and this one person made the job miserable for me. Being able to cut out this annoying aspect from my life by having only positive, confident, happy people who I enjoy apart of my life is the best gift of self employment.

3) Freedom to say NO


When you have an income source apart from a job, even if it’s just a side income, you have the confidence to know that you can stand on your own if you loose your job. You could even quit your job if it gets to unreasonable. Being able to say “I don’t need you” is a big confidence builder that can lead to even greater success down the road.

It’s why top performers in jobs are so successful and paid as such anyways. Because they have options. They’re not stuck.

4) Personal satisfaction of doing something different


When you have your own business, even if it’s only making $4,000 a month it’s YOUR $4,000 a month that YOU made. Yes you’re not rich by any stretch, but who cares. When I run into my former colleagues at PWC – some who are managers now making 6 figures a year, or even the partner who hired me that makes a million a year – they think I fell off the proverbial ship. That I’m awash in the sea of mediocrity. That I will never have the chance and opportunities I once did.

They are right to some degree… I have lost out on many professional opportunities – but little do they know that I swam to an island that I conquered for myself. Allowing myself many new and more interesting opportunities than they realize.

5) No ceiling on your income


When you have a job, you have a limit. This is OK if you have one of those good jobs that pays you enough to live…but with life in the west being expensive and costs being shifted from companies to employees; this limit is the biggest issue for most people.

Simply, people want to know how to make more money because jobs don’t pay you what your worth and what you need to live. You have to spend money on health care if you’re American, you need to fund your retirement, pay off college, buy a house, help your kids get through school, buy cars, pay for unexpected expenses, take care of your parents, and hopefully enjoy being alive!

Most job’s won’t pay enough to do all of this comfortably so why get one?

6) Not having to beg for money


I don’t want to have to ask for permission to be paid more. Now don’t get me wrong, being able to negotiate your salary is an immensely valuable skill but when you’re on your own you’re always working an never working. Building new things with the hopes they will pan out in the long run.

7) Diversified income streams


I got my start teaching English in Thailand and making a few hundred dollars from a few different websites. Over time I was able transition away from teaching to doing freelance at a much higher hourly rate.

I was also able to grow my passive income sources of affiliate income and advertising grew too. Allowing me to stop teaching and also do less freelance and more work on new passive income sources.

It’s wonderful having multiple streams of income. Even if you have a job, you should strive to make additional revenue from self employment.

8) Jobs are risky, ignore what boomers say


I was making $55,000 a year working 60 hours a week as a 23 year old guy right out of college back in 2007. Every month I got $3,000 in my bank account after taxes. Life was good. I was able to pay off the remaining balance of my college debt, save up some funds for retirement and not have to worry about money.

Until I quit at the worst moment in time.

The 2008 market crash made it all but impossible for me to recover with a new job that was anywhere equal in terms of allowing me to live; and just like that my income, retirement, savings and future were a big question mark.

Having a job is way to risky, I know first hand. I was stupid but brave to quit. Stupid because my timing could not be any worse. Brave because I don’t want that life of being a generic white guy in Connecticut living in a little apartment hoping and wishing for things to change.

I decided to change and life proverbially punched me in the face.

9) Financial Security


Starting a business is risky as is having a job, but if you pull it off by learning and adapting through failure you will be able to make your own income basket that has no limit, then another basket, then another, and another.

When you have a job and no income apart from it you live obediently. You can’t say what you think, you can’t be honest completely and tell the truth because you need the income. Otherwise if you screw up or say the wrong ting you’re in trouble. Gone is all of your income, benefits, and social life.

10) Jobs are dangerously comfortable


Everyone in my previous life were not happy with their job. They complained about the commute, the pay, the work, the hours, lack of flexibility, tiny vacation time (for Americans we get 2 weeks on average) etc.

Yet they buy products these companies sell us on, we watch their shows and what they create. We accept their vision of reality as truth for our own… and some even work for these very companies they despise.

When you work for someone else you get comfortable and lazy, you get set into a routine. You’re not really living. You’re just coasting and buying into vices to cover up the innate lack of personal fulfillment you get from working.

Fear keeps all of us in check, it prevents us from doing handstands on the proverbial ring of fire. But you limit yourself from doing something extraordinary because you fear failure. Don’t be mistaken, you should fear failure. I have failed. I have been broke. As a young person I can take more risk than someone who is 40 with kids – but failing is still terrible by any measure.

Regardless of your age however, you still need to answer the questions: How do you want to spend your days? What do you want to do for work? I think many won’t find the answer at a job.

Instead, take the leap. Figure out a way to become self employed. I use the Internet to make websites and consult. Convince your loved ones and have them support you. Then, follow through and don’t let them down.

11) When life blows up around you, you can adapt


Breaking up a relationship, having surgery, a loved one passes away, you get sick and need to sleep in, whatever. The nice thing about not having a job is not needing permission to take time to heal certain aspects of your life. You can be flexible with your time and take care of things without your employer thinking you’re lying or being lazy.

12) Unlimited vacation


As an American, the industry standard is 2 weeks of vacation a year for my home country. This is a crime. You need time to grow and expand your life and your mind. You need time to travel and experience new things. You can not have any meaningful experiences with only 2 uninterrupted weeks of freedom.

Yes you should go to the Maldives for a month. It’s beautiful. But you can’t. You only have 2 weeks, so it’s best to use that time to sleep in and recover from work. When you’re self employed you can take off time as you want.

I don’t need a 2 week vacation to recover from work because I’m not forced to be anywhere at any time. I can sleep in when I need to, and if I want to take a mini vacation to an island I can do that without asking permission from anyone.

This is my favorite thing about my life. I normally work 6 days a week, 5 days all day flat out. Saturday is a light day and Sunday I take off. But when I want to take a 5 day trip to Bali, I can. I just budget the time and I don’t need to ask anyone.

13) Be more productive and get more work done with a flexible schedule


People are up at 7 and back home by 6. Wouldn’t it be nice to work when you’r e most productive? For me that is usually after waking up around 9, having a 1 hour breakfast while listening to music, and taking a stroll through the markets to pick up some food for the afternoon.

This whole business of 9-5 started because of factories, but now with an information worker it makes no sense. Some people work best at night, or mid afternoon like me. I can work when I am most productive and spend the other part of my time learning a new language or traveling.

14) Get paid in your sleep


When you have a job you only get paid when you work. There’s nothing inherently wrong with this, particularly if you’re making the transition from having a job to being jobless by way of freelancing which is one of the best paths to get started on. But long term you want to build a proper business, and business are systems that operate without your constant direct input.

When I take one of my mini vacations and check my email seeing that I made affiliate commissions, ad revenue, and sales of my digital products, THAT’S a system. I can leave it alone and it works without me. Even this site you’re on now is an example of such a system that allows me to get paid based on the value I provide and not the amount of time I work.

15) LIVE anywhere


When you develop a skill that allows you to freelance and start building more passive income sources you can live anywhere.

I know it’s a tough adjustment to move abroad as it’s a whole new skill. But once you learn how it’s done you’ll never want to live in your little town in American again.

16) Learning how to support yourself without a job


When you have a job you gain limited experience at that job. Your mom will tell you that you need more experience to move up in the world but this is nonsense as you only repeat that limited experience over and over. This is fine until your skill set becomes obsolete. Then what?

Think of it this way – You are taught to have a job, why not learn how not having a job works and be self employed? That way you can do one or the other or both.

17) Having a job as your primary social outlet sucks


It’s ok to network with like minded people doing the same thing – but with jobs it tends to be social dead ends. When you want to grow as a person I find spending time with people who are where you want to be and cutting off people who are no longer a match essential for achieving goals.

With jobs though, it’s difficult to do this. Also if one of your friends quits or gets fired, do you lose a friend?

For me my social circle dried up after quitting. I “fell off the ship” as I like to call it and lost all connection to my peers. Many of whom I went to college with. I might as well have died.

Also, this happened before. When I worked in the Air Force as a crew chief – a male dominated work force, I never got to socialize with women. Imagine 20 years of never socializing with women at work?

No thanks.

When you have an Internet business that allows you to live and work anywhere, your whole world opens up new social connections that are much more fulfilling than hanging around with a bunch of dudes dressed in J Crew.

18) Force to learning how to make friends


When you’re on your own without a job or school to force you into a group, you need to make friends on your own. Some are naturally sociable. For others being self employed forces them to grow and expand this area of there life.

It may be painful and confusing at first, but once you can make friends, you know you can make friends anywhere you go – which makes you even more independent and free.

19) Have free time whenever you want or need


Most self employed people work and work and work. I know I do. But if I wanted to just drink coffee and read Wednesday afternoon I can. It goes without saying that this would not be possible with a job, but it’s a nice little benefit 🙂

Being self employed in a weird way means you're always working and conversely never working because you can adjust your schedule as you need to.

20) Prepare your own food


When you don’t have to get up a 7 am to rush for work at 8:15, you can actually sleep in and make your own food. When I worked at PWC we would always eat out for lunch and dinner. It’s part of office culture.

Yea you can try to “eat healthy” but when your work day involves sitting around in front of a laptop for 11 hours a day a it’s inevitable that you’re going to get fat.

When you work for yourself however you can prepare your own good food that’s also good for you and while you’re at it you can also make higher quality coffee or tea than you could ever get in an office.

21) No deferred retirement plan


When I worked at PWC I literally though wow I’m going to be 23-26 as an associate, then 27-30 as a senior associate, then 31-34 as a manager, then 35-40 as a senior manager, then if by the grace of the financial gods I would be on track to make partner by 40.

But wait! As a partner you need to pay about a million dollars to get into the partnership. So, 41-43 is paying off the debt to become a partner. Now at 44-55 I’m making over $500,000 to $800,000 a year. By the time I’m 55 I can retire and be set for life.

This it what is meant be deferred retirement.

Work during your good years so you can retire and then enjoy life. How about this?

Enjoy life now. Have lot’s flings with beautiful girls now. Travel and do cool stuff now.

Unlike the work-aholic Gary Vee’s of the world, you don’t live forever. You will die. Is work and crushing all that you want to experience? What about 9 hours spend at a cubicle?

Travel now when you’re young, healthy, and the ladies still take a liking to you. Money matters, but you don’t take it with you and you’re going to be dead soon enough.

We all need time to rejuvinate our lives. I like to go for motorcycle rides, read, and wander around a new place when I need to take a week or so off. You can’t do that with a job.

22) You don’t have to sit at a desk


You also don’t have to shop at J Crew and the Banana republic. Beige no longer needs to be your favorite color. You can also skip out on shaving for a day or two if you like and look like a man instead of man child.

That's not to say desks are bad. I'm writing this from a cafe at the moment, but when I'm home I work from a desk. I just don't have to stay at desk for 8 hours all day everyday.

23) Being able to be outside in the sun


When I worked as an air craft mechanic in the Air Force reserve, I hated being out in the cold winters working on a plane. When I was working in an office I hated being couped up inside when it was so beautiful out. When you have a job, you don’t even have the freedom to choose when you can go outside and for how long.

24) Do meaningful work


Jobs don’t want you to change the world or help people, they want you to put the “customer/client” first and maintain the status quo. When you don’t have a job, you can focus on important projects that make a difference.

You can focus your work to help people, and you can leverage your flexible schedule to participate in projects that are making a difference. I enjoy volunteer teaching in poor villages out in rural Asia. I dictate when I volunteer and when. Not a job.


25) You can try again and again.


You will most likely never build long term wealth with a job. There are exceptions like this investment banker, but most will be just over broke (JOB). Entrepreneurship is the only means (apart form a lottery or casino) that allows the average person who is of reasonable intelligence and born in a western democracy to obtain wealth.

With sports, you get one shot. With music you get one shot. With acting, you get one shot. But entrepreneurship? You can fail again and again my friend and still get back on that damn horse.

26) Being jobless on your own terms keeps you alive and well


Imagine being able to sleep when you need to, go to the places when you want, work when your most productive. Also imagine having to make friends yourself, manage your time on your own, be creative and think of solutions to novel problems.

Taking the very risk itself to do what you want and accepting the uncertainty of doing your own thing keeps you on your toes. It makes you more alive, more human and a better more interesting, attractive, and dynamic person in the long run.

What is the worst case scenario? How likely is it? Whats the best case scenario? Regardless of what you do or don’t do one thing is for certain. You’re going to be dead soon. You might as well get busy doing fun stuff.


Never have a job conclusion


Does this mean you don’t work? No – unless you’re rich you always need to work – it comes down to how you want to spend your time? I don’t have the answers. I’m the impostor. For all my mistakes and the way my life set me up for failure, I should be working in a warehouse driving a fork lift living a sad life in Connecticut.

But I’m not – I carved my own path and know from experience that working for myself is so much better than having a job.

I’m not sure if this is for everyone, but if you’re looking for a freer path you can have it if you’re willing to sacrifice and struggle for what yo want.