Why you should NOT work for yourself (right away)
Published on January 24th, 2007
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What should I do with my life? That is the question almost all of us wondered at some point. Even if you knew from the beginning that your destiny lies in the field of, say, financial accounting, one question still remains relevant – should you go out and get a job working for “the man” or start your own business?
Traditionally, the self-help industry’s standard advice has been to do your own thing. Books like “Rich Dad, Poor Dad” go into great detail as to why it is preferred to work for yourself. The personal development blogosphere has been echoing the same advice. And in fact, I wholeheartedly agree that there is no better way to achieve success and financial independence than to be your own boss.
However, I don’t think that people should be blindly accepting what authority dictates. Starting a business might have worked for the author, but it may not be the prescription for you. I think the smarter thing would be to consider the benefits and drawbacks of both, and then decide for yourself.
In his excellent book “Hackers and Painters”, Paul Graham discusses the concept of working for someone else as being unnatural. Throughout human history, people were always working for themselves (when they had freedom to do so.) It was only with the advent of industrial age that the notion of being an employee has been widely implemented. So, Paul makes an argument that being an employee is unnatural and everybody should start a business.
I disagree. At least at one point in human history, there was an example of a very healthy employer/employee relationship that worked well for both parties – namely, the master/apprentice relationship.
In medieval/renaissance times, there were artisans – masters of their craft. For example, a town usually had a blacksmith, whose job was to make and repair horseshoes, ploughs, swords and everything else made of metal. If business was flourishing, blacksmith could not handle the load by himself, and some other man in the village might send his son to serve as blacksmith’s apprentice. Blacksmith provided his food and lodging, and taught him the craft. In exchange, the apprentice helped him in the forge. Eventually, after the apprentice matured and learned enough to go off on his own, he would open a blacksmith business if he were so inclined. (This, of course, is a perfect scenario. As we all know, in real life things don’t always work out as they’re supposed to)
A lot of personal development books and blogs describe the modern employee/employer relationship as master and slave. In my opinion, this is not always the outcome. If you start to think of yourself as your employer’s apprentice, you’ll see many benefits for yourself. Your employer pays your salary (provides food and lodgings) and lets you learn the trade and build a network of contacts. In return, you do work they require of you.
If you have high ambitions (and I imagine most of my readers do), working for others is probably not something you want to do all your life (I know I don’t.) But if you look at it as apprenticeship, and use it to gain real-world skills, it’s going to be time well spent.
In the same book, Paul Graham talks about the intangible skill to “get it done” – something that distinguishes kids from adults. It’s the ability to complete the work, no matter how boring and tedious, because that’s what you have to do. This is the reason employers are reluctant to hire college grads – most of them don’t have it. In college, if you don’t want to do something, then you don’t. However, that luxury does not exist in the real word.
Where else are you going to get that ability, if not working at a real job? If you open a startup right after college, are you going to have the strength of character required to complete mundane and boring tasks? Your chances are much greater if you get real world experience at a job, and only then branch out on your own.
Of course, starting your business part time while working a full-time job is not easy. But then again, what is? Succeeding in business world requires tremendous effort and dedication. If you can not pull of starting your business part time, then the future does not look bright.
I’m in that boat right now - working a full-time job, trying to start a business and work on this blog in my spare time. The proponents of “don’t get a job” movement will be quick to point out that if I didn’t spend best part of the day working for “the man”, my business would already be up and running. The reality of the matter is that if I didn’t work for my company, I would not be where I am today. I wouldn’t have the necessary skills, maturity and perseverance that are necessary to get anything done.
I’m not suggesting that every fledgling entrepreneur puts his or her dream on hold and brushes off the resume. I am, however, stressing that you should consider your options and think for yourself before following somebody else’s advice. Maybe you have matured enough and learned all necessary skills by the age of 14. Or maybe you don’t know anything about starting a business other than “it would be cool to …”
Whatever you do, decide what’s best for you. And then, hopefully, we’ll see an increase in number of successful businesses and happy people all over the world 
January 25th, 2007 at 1:49 pm
Nice post. I get what you mean. It isn’t realistic for everyone to start their own business without real world knowledge. Still, I can’t wait for the day when I can set my own hours.
January 26th, 2007 at 12:32 am
Thanks John!
I’m a little afraid of that though, because I’m probably going to spend so many hours on my business that my current 8-6 schedule would seem like part-time work 
I can’t wait until I can set my own hours either
January 26th, 2007 at 9:31 am
Hi Alex,
Super stuff. I havent come across anyone who could have put it across more simply. I personally think you are doing an awesome job, writing this content. Best Of Luck !
rgds
N.Kartik
Bangalore, India.
January 27th, 2007 at 5:32 pm
Your reframing of the relationship between employee/employer is awesome. I 100% agree with you on your point of using the structure of working for a company to become mature enough to run your own show. Best of luck with your personal projects!
January 29th, 2007 at 3:19 pm
Hear hear! From another crazy person working a fulltime job for someone else and a (now) fulltime job for myself as well, I agree whole-heartedly!
It’s not easy, but it’s not as hard as others might think.
Rebecca
February 12th, 2007 at 1:56 am
Interesting that you bring up Paul Graham in this context. Becuase when you take money from Paul’s seed fund, Y Combinator, you work for Y Combinator, right? I mean, they own a percentage of the company, and you probably aren’t going to do anything that Paul tells you is a stupid move.
So Paul is actually an example of that positive employee/employer relationship you’re talking about. Because he calls a lot of shots, but people who take his seed money seem to really like having that relationship with him.
February 12th, 2007 at 10:58 pm
That’s a very interesting point, Penelope.
I wouldn’t exactly look at Y Combinator’s relationship with companies they invest in as employer/employee. PG always emphasizes that they take only a small percentage and leave full creative control to the companies.
But you’re totally right, profit sharing is a very good example of a positive employer/employee relationship. I think what’s missing in a typical corporate environment for a lot of people is the fact that no matter how much you sweat, you generally won’t get far ahead in terms of salary (there’s a lot of exceptions to that, of course.)
I can only imagine how motivated would every employee in a company be if they knew they were in full control of how much they earn.
July 19th, 2007 at 1:58 am
You do realize that these artisan’s who had these apprentices worked for themselves right? And the apprentice would one day take over and then in turn work for himself. The master teaches the student then the student becomes the master. So it still looks to me that it is in human nature to work for yourself. If anyone can tell me that they like working for someone else I would ask them when the last time they had a cat scan was. Why work for someone who thinks your stupid and worthless? When you know that you are smarter than your boss…its time to become the boss. Take for example my boss before I broke away from the slavery that is working for a company, she had gotten the job from her sister had never finshed even high school, and yet felt she was something of a god. I’m not saying that a degree makes you anything better than someone without one, because what I do requires no degree only skill, however treating someone with a higher education than you like an infant seems a bit…well for a lack of a better word stupid.
July 24th, 2007 at 10:23 pm
Thanks for your comment, selfaddict.
Sorry to hear that you had a bad experience working for someone. But I’m glad it motivated you to go out there and work for yourself!
I think you missed my point a little about the master/apprentice relationship. What I was trying to say with that is that apprentice got all his skills and experience while working for someone else - the master. That’s the experience he wouldn’t have gotten otherwise.
And, of course, once he’s ready to go off by himself, he did. But all the preparation for that moment, all the skills, connections (customer base!), etc. - he got by working on someone else’s time.
Don’t get me wrong, I’m not trying to advocate everybody joining the corporate world and working there for a few years, learning the ropes and paying their dues. That stuff is definitely not for everybody.
I just see so many people out there online that making blanket statements like “you’re better off working for yourself” without considering any context or circumstances, that I tried to point out an example of a situation where you’d be better off STARTING by working for someone else.
January 22nd, 2008 at 10:56 pm
All,
I currently work for myself as of 11/01. I am now very close to getting a full time job and working for the man. Working for yourself can be as great and rewarding as working for someone else. Making your own hours can be as great as working a 9-5 job. you need to decide the opportunity cost for working for yourself and realize that you are taking a risk. I am taking a risk closing my company and working for someone else. The great thing is working for someone else “in general” you make mistakes and it’s the company who will probably pay for the mistake. If you own your own company and you make a mistake that could be the end of your company. The reason I am going to work full time is I am bored, burnt out, lost my passion for my business. I don’t have employees and I work from home, have little fixed expenses and no variable expenses so my overhead is low but I constantly need to find new clients to gain incomen and in the competitive market that is difficult. Probably if I partnered up with someone I could continue and be doing well. Who knows that once I work for the man I may miss what I had but I have nothing to loose and everything to gain as I know I will be getting a paycheck every week (of course there is always the possibility of being laid off I understand). Working for yourself is no gaurantee you will be receiving income.
June 22nd, 2009 at 4:28 pm
Good to see this post.
Weird that it came up in a Google search on “bored”. But you know I AM!
I did this. Spent 20 years in engineering companies as an IT guy, and started a consultancy after two dot bombs in a row. It was the most fun. But my wife likes the benefits where I work today. Even though I am frustrated and bored here.
Before I started my company I went to a local non-profit who sponsored a small business workshop. (http://www.cbdc.org/) Very helpful. I definitely recommend attending something like that before you go solo. You can find seminars through the small business administration here in the states.