Part of the American entrepreneurial dream is the fantasy people have about being their own boss, but there are three very good reasons why people would rather have a boss (I.e., keep their day jobs). All three reasons have to do with simplicity. When you are subordinate to someone else, live can be simple and well-defined, but when you are your own boss there are all kinds of nagging complexities to deal with. If you are thinking about quitting your day job and working for yourself, consider the following:
Reason to Have a Boss Rather Than Be Your Own Boss #1: You can please one person, instead of dozens. When you have a boss, it is obvious who you need to keep happy: Your boss. Of course you have to deal with other people. You might have to handle client communications, work with suppliers, or deal with various coworkers. Ultimately, though, there is only one person you really need to please: Your boss. Contrast this to the entrepreneurial be-your-own-boss situation: If you are the top man/woman in an organization (even if it is an organization of one), you are personally responsible for keeping all those customers, vendors, and employees happy. Instead of focusing on one boss, you have to divide your attention among many, many people, and that can be unpleasant and tiresome.
Reason to Have a Boss Rather Than Be Your Own Boss #2: Work is provided, no rainmaking required. When you work for a boss, you might find yourself complaining about the low-grade work he/she provides, or about the way he/she micromanages your work. Do not forget, though, that the boss is providing you with work. When he/she asks you to complete a project, all you have to do is complete the project. Contrast this to the be-your-own-boss / entrepreneur scenario: There, you have to find your own work, and that means rainmaking. You have to solicit business, and then get it down (two steps instead of one). Your boss is providing you a valuable service by handing you prepackaged work.
Reason to Have a Boss Rather Than Be Your Own Boss #3: You do not have a target on your back. One of the advantages of being an underling is that no one is gunning for your spot. You can blithely go along, day after day, doing what you do, without watching your back for potential competitors. If you are your own boss, though, anyone lower than you in your organization might try to usurp your position. Even if you are an organization of one, there are competitors trying to be what you are. This high level of competition can be stressful and unpleasant.
The freedom of being your own boss is not as free as it might seem; before you leave your current job, consider all the benefits of keeping your day job and putting up with that boss of yours.