It’s Monday morning in Oakland, California, as I’m writing this. I’m sipping a cup of coffee, looking at the rolling hills behind Berkeley from a coffee shop in Rockridge. Clouds are rolling in from the Bay, it’s absolutely stunning.

A few days ago Maren Kate of Escaping the 9-5 interviewed me about achieving online business success (I’ll let you know when the Interview goes live on Twitter,) and it got me thinking: it’s almost been a year since I had a ‘job’ in the assumed sense of the word.

In hindsight, it seems so silly that I had one to begin with. There are just so many benefits to not having one these days.

Having a job might be good for some people, but it isn’t for everyone –contrary to what everyone will tell you.

The long hours, the designated tasks, having to run plans by colleagues or bosses before putting your plans into action seems like far too much to ask after a year of minimalist freedom.

We grow up with this idea that we’re supposed to train for the “workforce”. Most of our parents had jobs, all of our friends want to get jobs, all of the advertisements tell you to buy stuff in order to make you happier at your job.

Having a job is in many ways a lot easier than choosing not to have one.

When you have a job, you typically are told what to do. Someone at one point or another wrote the call script for your life, and all you have to do is follow along until the clock hits 5, and then it’s happy hour.

We didn’t always have jobs.

Seth Godin likes to bring up this little fact in his Linchpin sessions: at the first factories they literally had men pushing carts of gin back and forth on the factory floor. People were so unaccustomed to working for hours straight that their owners had to keep them drunk all day in order to keep them happy enough to continue to do a good day’s work.

Gradually we’ve trained a workforce that’s a little more into the idea of working long hours, so the gin carts are now mostly unnecessary –though I’ve known plenty of colleagues who kept bottles of whiskey in their desk drawers just to stay sane when they had to stay late.

Why minimalism can free you from being required to have a job.

The brilliant thing about minimalism, when applied in the strictest sense of the philosophy, is that it can free you from needing to have a job.

• When you live with less than 100 things, you don’t need disposable income to stay happy.
• When you free up your schedule, you can pursue work that matters.
• When you stop the weekend shopping sprees, you don’t need a huge house to store all of that stuff you don’t need.

This all leads to having a base life-overhead which is much smaller than everyone else. When you have less overhead, you can have the freedom to begin working for yourself.

I won’t spend too much time on how minimalism can reduce your overhead. If you’re interested in pursuing a minimalist life, check out my e-book The Art of Being Minimalist, or my friend Daniel Richards’ new e-book Doing With Less.

What I’m interested in conveying to you is the benefits of not having a job.

Yes, not having a job isn’t for everyone. Some people enjoy being told what to do, and other people have jobs they really love. I wouldn’t want anyone to leave a situation that they really enjoyed simply because of an article I wrote.

The most important fact to consider is that not having a job isn’t easy. Starting a minimalist business with no-overhead that runs itself can be challenging. It might involve long hours in the beginning, and relies on individual creativity to succeed. No one can hand you the magic bullet that will tell you how to create income that doesn’t come from having a job.

Ultimately you need to trust yourself, and follow the path that feels right for you.

Here are 27 reasons why you should never have a job.

1. Financial security.

Creating your own business can be much more financially secure than having a job. At a job, all of your income is in one basket, which is the farthest thing from financial security that I can think of. Many people with jobs live in endless fear of losing them, because if they did the money just stops coming. If you screw up, or say the wrong thing, poof! There goes all of your income, your benefits, and sometimes your social life all at once.

2. Diversified income streams.

When you have your own business, you can concentrate on having diversified income streams. A job pays you all at once, and if you lose it all of your money goes away. With a minimalist business, you can develop variable income sources. If one dries up, the others still thrive. Some income will be small and occasional, other income will be large and regular. The most important aspect is that it’s all coming from different sources, and nothing can go wrong with them all at once, like when you have a job.

3. Contribute value to your legacy.

When you have a job, you’re contributing value to the legacy of an organization that is bigger than you. That usually means that the legacy is separate from your own. Yes, you can create great work at a company, but chances are you won’t be bragging about the stunning TPS report design you did at company X to your grandchildren. When you create your own business, you’re contributing value to your own lasting legacy.

4. Live anywhere.

When you create your own business, especially on the Internet, you can live anywhere in the world. For instance, last week I moved from Brooklyn, NY to Oakland, CA. I never could have done that if I had to go into an office, because they would decide where I lived. Some job markets are stronger than others. In my experience, strong job markets usually coincide with expensive or crappy living conditions. By freeing yourself from location, and not having a job, you can live anywhere in the world. A great resource for learning to live anywhere is Karol Gajda’s How to Live Anywhere, coming June 8th.

5. Unlimited vacation.

Face it, two weeks of vacation a year is a crime. Whoever decided people should work 50 weeks out of the year was absolutely insane. How this was adopted as an industry standard is beyond me. When you create your own business, you can develop a more flexible vacation schedule. 25 weeks a year? Go for it!

6. Choose your own path.

When you have a job, chances are you’ll be told exactly what to do every day. Handle this client, print that TSP report, sit at your desk for 8-10 hours a day! When you create your own business, you can choose your own path. Obviously, this also means that you can choose the wrong one. But in my experience, even the wrong paths are much more interesting than sitting at a desk all day. Yes, you’ll make mistakes. Yes, it isn’t easy. But wouldn’t you rather have an exciting life than a dull one under fluorescent lights?

7. Flexible schedule.

One of the best reasons not to have a job is having a flexible schedule. At a job you have to be there Mon-Fri 9-5, or something like that. When you create your own job, you can work when you’re most productive. Some people work best in the middle of the night, others work best in the afternoons. I’ve found that I can usually create quality material in a few hours every week, freeing myself to do other things that matter to me, like practicing Yoga.

8. Avoid reactionary workflow.

There’s an always-on mentality that is quickly coming to dominate our society. We feel like we must be on our crackberries and iPhones every single hour of the day, just in case something happens. The reality is that nothing important really happens, our minds only make it that way. When you don’t have a job, no one will force you to answer your email in the middle of the night. This frees you up to focus on the work that matters, and creating powerful passive income streams.

9. You don’t have to conform to other people’s expectations.

It’s no secret that one of my favorite small business writers is Chris Guillebeau, who writes The Art of Non-conformity, and his small business guide The Unconventional Guide to Working For Yourself. We often forget how weird it is to opt-out of the the idea of having a job, but it is pretty strange for a lot of people. The best part of not having a job is that you don’t have to conform to other people’s expectations. You can be weird if you want to be, and no one will fire you for it. The funny thing is, weird is one of the best niches to set up your small business in — there’s too much regular out there already.

10. Making money in your sleep.

Oh, have I mentioned when you start your own online business, there’s a very real possibility that you’ll make money in your sleep? Well, there is. There’s nothing like checking your email (once a day) and seeing that you made all the income you need to survive using automated means while you were taking a snooze. It’s definitely worth quitting your job to experience that freedom.

11. Freedom to be a leader.

Jobs are built around conformity, that’s why everyone is expected to wear ‘work appropriate clothing’ that they purchased at J. Crew. What does conformity do? It makes it possible for upper management to keep the lower levels in line, on task, and compliant. When you opt out of having a job, it frees you to be a leader. A leader has to stand out, and have vision. A leader has to show people the way by telling the truth as it is. The truth is that business casual isn’t something you have to subject yourself.

12. Choose work that excites you.

Most jobs are made up of mundane activities that someone higher up in the food chain asked you to do. File that TPS, buddy, or you’re going to be stuck in middle-management forever! When you don’t have a job, you can choose work that excites you. Do you want to create a product that teaches people how to live a passionate life, like my friend Henri Juntilla? Go for it!

13. Surround yourself with people you care about.

When you have a job, someone else chooses who you spend your time with during 60% of your life. In some of these cases, you’re stuck with people who you don’t particularly care for. These might be company lifers, or dead-eyed soul-sucked individuals who opted out of living life years ago. When you work for yourself, you can pick your own social circle. As my friend Glen Allsopp likes to mention, you’re going to be as successful as your social circle. So pick people to hang around with who have a lot of money coming in –they also will be more inclined to buy you beers than boring company lifers.

14. Sleep whenever you want.

Different people sleep different. For instance, now that I’m in California, I’ve been waking up early in the morning (by California standards), because I used to wake up at 10am in New York. When you have a job, someone else is determining when you wake up. Maybe you’re the kind of person who enjoys staying up until 4am working on projects that matter to you? If you don’t have a job, you totally can.

15. The ultimate ROWE environment.

One of the newest fads in workplace civil rights is the idea of the Results Only Work Environment (or ROWE). My friend Jeffrey F. Tang wrote an article about ROWE here. Well, not having a job is the ultimate ROWE, because the only thing that matters is your results. When you have a job, unless you work at a hip progressive ROWE company, chances are you’re only rewarded for sitting at a desk (6 hours Facebook, 2 hours actual work! Yay!.) Well, some people don’t work well sitting at desks, believe it or not. When you start your own business, only the results matter, no one cares if you get them while plopped in a desk.

16. Work on projects which will change the world.

The most profitable projects, in my experience, are also ones that change the world. When you work at a job, chances are no one really wants you to do any world changing. They just want you to maintain the status-quo. When you don’t have a job, this frees you to work on projects that will change the world. Maybe you want to teach people how to live without their cars, like my friend Tammy Strobel does in her e-book Simply Car-free. Or maybe you want to sew sustainable puppy blankets. The change you make is up to you.

17. You only have to make yourself (and maybe your significant other) happy.

When you have a job, you have to make your boss happy, your colleagues happy, and if you don’t well, then that single source of income we talked about earlier is on the line. When you don’t have a job, the only person you have to make happy is yourself –and possibly your significant other. What I’ve discovered, in my nearly a year of not having a job, is that it’s much easier to make yourself happy when you’re not trying to make everyone else happy at the same time.

18. Prepare your own food.

This is key. When I used to have a job, I’d constantly get food out. I ate at my desk, because I was afraid if I was away for more than 15 minutes all hell would break loose. When you work for yourself, you can also work in your kitchen (which I do often!) This means you can prepare healthy food, that tastes good. You can also make your own coffee (so much better than office coffee.) Making your own hot food while you take a break from work is so much better than packing a lunch and heating it up in the microwave.

19. No waiting for retirement.

Just wait until you’re 65, then you can do whatever you want. Seriously? I think you should do things while you’re young, athletic, and the ladies (or lads) still like you to look at you. Face it, waiting for retirement to get more than 2 weeks of vacation is a crime against your humanity. When you work for yourself, you can retire whenever you want for however long you need — as long as you have the resources. The truth is that we need time off to rejuvenate our ability to live. I like to take weeks at a time when I do very little except Yoga, reading, and wandering aimlessly. You can’t wander aimlessly on a Wednesday morning when you have a job. The funny thing is, the best ideas come when you’re not working for them. Bonus: take a year off every seven years like Stefan Sagmeister does.

20. Time to focus on the important.

When I had a job, I never had enough time to do what was important to me. On the forefront of my mind was always the task at hand at my job, whether or not I actually cared. When you don’t have a job, you can focus on what is important to you. This is different for everyone, as everyone is different.

21. Cool people don’t have jobs anymore.

Face it, it’s so cool to tell people that you’re self-employed. However, it’s not cool to brag about the fact that you have the best hours, a flexible work schedule, and that you get to work on things that matter in front of people who have jobs. Don’t rub it in, the best self-employed rockstars show, they don’t tell.

22. Work from wherever you want.

Today I edited this post from the awesome kitchen in my brand-new apartment in Oakland’s hopping Temescal ‘hood, I wrote most of the post while I was grabbing a coffee over in Rockridge. One of the biggest benefits of working for yourself is that it doesn’t matter where you work. You could be on a beach somewhere, you could be at a coffee shop, you could backpack through India. Location doesn’t matter when you’re living the digital lifestyle.

23. Working for yourself is the best way to approach work in a recession.

Look around you, no important businesses are hiring anymore. Big businesses are hunkered down and waiting for us to come out of this recession. You can either wait until the recession is over to find the job you truly desire, or you can settle for less than the best. The Subway sandwich shop near me is hiring “Sandwich Artists”, but that doesn’t mean you should apply there.

24. Showers in the middle of the day.

This probably goes without saying, but it’s pretty sweet to be able to take a hot shower in the middle of a Monday afternoon. That wouldn’t be possible at a job.

25. Multiple paydays.

When you have a job, all of your income comes from one place, and you know when it comes. This means if the section of the economy where your job is located collapses, your only paycheck is on the line (as mentioned above.) But it also means that you know exactly when you’re being paid. When you don’t have a job, your pay can come from all different directions, and at different times. This replaces the monotony of knowing with the fun uncertainty and improvisation that comes with multiple paydays.

26. You don’t have to sit at a desk under fluorescent lights all day.

Sitting at a desk all day has been proven to be incredibly bad for your health. Some people are incredibly product at desks, but many of us aren’t. I think of most of my ideas when I’m walking. Maybe you think of your ideas while standing on your head. Sitting at a desk all day is just something we do because someone told us to, not because it’s a useful practice.

27. Uncertainty keeps you on your toes.

Jobs seem so certain. You’re protected from the harsh realities of the world in a lot of situations. This can be a good thing, but it also keeps you in the dark. I’m convinced that we grow with uncertainty. It makes us thrive, because we’re constantly adapting and changing our strategies. This means that you’ll never stop learning when you’re working for yourself, as your free to try new things and take new paths.

The reality of the situation is working for yourself is one of the best ways to improvise and ultimately survive in this boom-and-bust economy.

Does that mean that you won’t have to work hard? certainly not. There are no magic ‘get rich in your sleep’ solutions, there is only the hard work that you need to do to set yourself up to leave your job and set out on your own.

I don’t have all of the answers, but I do know that working for yourself is so much better than having a job. Is it for everyone? certainly not. But if you want to pursue a freer reality, this may be the answer you’re looking for.

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