Last Updated 10 May 2020

The Top 5 Reasons Not to Become an Entrepreneur

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The reasons for becoming an entrepreneur are widely known and extolled, but there are some of you out there right now who might be considering becoming an entrepreneur for all the wrong reasons. So in an effort to impart some of my meager wisdom on the subject, I submit to you the top five reasons for not becoming and entrepreneur:

1. Because you hate your job.

I have very little patience for people who hate their jobs -- if you hate your job get another one and quit (in that order). As I’ve said previously, it’s generally not like you were a runaway and a stranger picked you up at the bus station, fed you and gave you shelter, and then one day told you that you had to earn your keep and beat you until you agreed to become an accountant. If hating your job drives your decision to turn in your notice and start your own company, you will fail. Of this I am certain. You see, if you hate what you do for someone else you will probably hate what you do for yourself, only more so.

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Become an entrepreneur because you love your job; because it excites you and fills you with passion. If you love what you do you might as well reap the benefits of your labor.

2. Because you hate your boss.

Hate is such a strong and ugly word that it should be reserved for only the most loathsome bottom-feeders in our society. Unfortunately, I’ve worked for a couple of truly reprehensible lying, dishonest, amoral, steaming piles of iniquity; but still, I can’t even bring myself to hate these members of Satan’s entourage. I’m convinced that the only reason that one of them in particular is still alive is because Lucifer is keeping him safe—he hasn’t been the CEO of Hell for all this time to have this clown usurp his position because he fell down a flight of stairs and suddenly find himself fetching his new boss coffee and answering his phones. No hating your boss is a bad reason to become an entrepreneur because there is so much you can learn from a truly imbecilic boss or manager. You not only learn what NOT to do in business, but when you ultimately decide to become an entrepreneur you will know your competition’s weaknesses and be positioned to capitalize on them. It may sound Machiavellian but who better to put the screws to than someone who has mistreated you, cheated you, or otherwise made your life a living well…Hell?

3. Because you hate working for anyone.

A fair amount of people become entrepreneurs because they just can’t stand having a boss. In these people’s minds the best way to not have to answer to anyone is to become an entrepreneur. When you are an entrepreneur, everybody is your boss -- most entrepreneur enterprises live or die by word of mouth and it might make you feel powerful telling someone that you don’t need their business, or that they aren’t welcome back in your establishment, but when you do so you aren’t just barring one person from doing business with you, but that person and probably everyone they know. If you become an entrepreneur because you can’t stand working for someone else you generally end up having a social maladroit for a boss.


4. Because you dream of doing something new.

I am going to pick on restauranteurs for just a moment. Yes I know that there are many terrific restaurants run by shrewd business people, but for every one of these, I know 15 restaurants that are poorly run by husband and wife teams who have always wanted to own a restaurant. They retire and blow their entire savings on a business because their sole qualification for running a restaurant is having eaten at one once. I’m not saying you shouldn’t follow your dream, but if your dream involves doing something about which you know next to nothing, invest some time learning the ins and outs of the business before striking out on your own.

5. Because you’re lazy.

Lazy people become (mostly failed) entrepreneurs far more often than you might think. Entrepreneurship sounds downright easy: you are your own boss, you set your own hours, and you call all the shots. While all of these are technically true they may not mean what you think they do. You are your own boss, but that doesn’t mean that you don’t answer to people; customers, creditors, vendors, regulators, and employees, all have the power to shut you down so you do have to answer to them (or at least be prepared for the consequences).

Near my home there is a corner liquor/convenience store. It was owned by a great couple one who worked opposite shifts. It reminded me of Drucker’s Store from Green Acres; the neighborhood regulars would pay 30 percent more for snacks or the odd can of soup and hang around talking to the others. Unfortunately, the couple burnt out on running the store (which for the record was more than just a little successful) because it meant they never got to see each other, could never take a vacation, and both of them working two jobs was just too much. They sold it to a retired policeman who never quite made the adjustment from having the authority and power of an officer of the law. I would walk my dogs and stop in and buy two bottles of Diet Pepsi to drink on the walk. I did this twice a day. One day he was out of Diet Pepsi, and I asked him what was going on. “Soda comes in on Thursdays,” he barked back. I explained to him that I bought it every day not just on Thursday, and what’s more I had been doing it for over a year. “Soda comes in on Thursday,” he said in his best, “If I tell you again I’m taking you to jail" cop voice. I went to another store and bought my sodas. The owner, also a friend, asked why I didn’t just come in to his store when I was on my walks, and I told him I had my dogs.  He said, “bring them in -- I don’t serve food so there is no reason that they can’t come in." I went there every day after and the other store went out of business.


You do set your own hours, but if you don’t keep regular business hours you will fail to attract a clientele, and as far as calling all the shots, this is true, but it also means responsibility for all mistakes and bad business decisions.

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