Starting a business is part of the American Dream, isn’t it? For many people, becoming your own boss ranks right up there, along with owning a home, making a good living, and living a life of freedom.


But it’s not for everybody.


I have known quite a few people who have put a lot of time, money, effort, forethought, and energy into becoming an entrepreneur only to find that they didn’t like the gig too much after all. They were surprised, of course. When you plan to take on something as big as starting your own business, you expect that you’ll like it. But, for various reasons – the time involved, the ups and downs, the lack of structure, finances – it doesn’t always work out.


Some people are athletes, some are musicians, some are better at being employees, and some people are meant to be entrepreneurs. We are all different, and you need to be sure entrepreneurship is right for you before you jump into the deep end of capitalism.


Here’s some food for thought that can help you begin to answer that question: Think about your job. Think about your boss, your paycheck, your benefits, your co-workers, the work you love, and the work you hate – everything – and then think about leaving all of that behind.


Does the thought make you more scared or excited?


If leaving gets you more excited than scared, then you are on the right path towards entrepreneurship. You will notice that I did not say that you should not be scared at all, anyone in their right mind should be a little nervous at the thought of leaving the security of a job for the uncertainty of a new business. But for the entrepreneur at heart, the excitement outweighs the fear.


Beyond that, there are several other things to consider before starting your own business.


For starters, do you have the support of your family? Entrepreneurship is tough enough, but it is doubly difficult if your partner is not on board. When I left the “security” of the big law firm, my wife was pregnant with our second child, yet she signed off on my dream to start my own law firm because she knew that 1) I was not cut out to be an employee, and 2) it was, in fact, my dream to be self-employed.


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Do you have the resources needed to do it the right way? Of course, there are times when you have to go off on your own when the circumstances are less than ideal – you got fired, for instance – but it is far better if you can do it the right way. That means having enough money to start the business, lease an office or store, buy inventory, and be able to live for at least six months. I say six months because that is the amount of time it will take, generally speaking, to open up shop, get customers, do some work, invoice, and get paid.


Starting a business on a shoestring is doable, and in some ways smart, but you also must be smart and prudent. If you are going to be giving up your steady paycheck, you have to have the resources on hand to be able to absorb that hit for a while.


Are you able to live with uncertainty? One of the great things about working for someone else is that there is built-in structure. Someone else is the rainmaker and brings in the money and the work. You get a regular paycheck. You have colleagues and people with whom you work. Even something as simple as supplies are handled by someone else. But, this is not the case when you become the boss, especially at the beginning when it will necessarily be a small venture and you will have to wear many hats.


If you read my articles regularly here at the Bank of America Small Business Community (or at, then you know I am an unabashed advocate for entrepreneurship. But that said, I also know it is not a path to be undertaken lightly. So be sure to consider all of the ramifications, both good and bad, before you start your journey.

About Steve Strauss

Steven D. Strauss is one of the world's leading experts on small business and is a lawyer, writer, and speaker. The senior small business columnist for USA Today, his Ask an Expert column is one of the most highly-syndicated business columns in the country. He is the best-selling author of 17 books, including his latest,The Small Business Bible, now out in a completely updated third edition. You can listen to his weekly podcast, Small Business Success, visit his new website TheSelfEmployed, and follow him on Twitter. © Steven D. Strauss.

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