We all have moments in our lives that help define who we are and how we view the world.  I have spent most of my working life self-employed for many different reasons; however, there is a specific experience that is one of those defining moments in my life that made me believe that I could never work for someone else, particularly, a large, impersonal corporation.

I took a year off from my law school studies and worked in the Boston office of a large, national financial institution preparing credit reports on small businesses.   There was a senior credit reporter who had been in that office for many years and appeared to be the most knowledgeable employee in the office.

He prepared the credit reports for the largest businesses and was the person everyone went to with questions and problems, including his boss.   That was the first thing that caught my attention.  This man appeared to be the most valuable person in the office, yet, he was not the boss.  It made me feel that knowledge and experience are not always properly rewarded.   By any rational standard, his value to the company should have put him in a position of power instead he was, in many ways, just another employee.

The clincher for me was when this man retired.   After many years of service, his retirement send off consisted of a brief ceremony in front of the other employees with his wife in attendance.  The boss spoke a few kind words, his wife was given some flowers, he was given the obligatory gold watch and then it was over in just a few minutes.

As I watched this unfold, I felt sadness for the man whose long career seemed to be marginalized by such a trite farewell and I was struck by the fact that he left with a gold watch but without the full measure of respect that I thought he deserved.   Perhaps, the reality of his retirement was much better than it appeared, but, that is how it seemed to me as an impressionable twenty four year old.

I look back on that day as one distinct moment when I realized that I would not spend my life in the service of someone else.  I soon left that job and went back to law school.  Now, as I am approaching retirement, I still believe that being self-employed was the best choice for me.



There is a sense of security in having a steady job with a good salary and benefits.   I call this security your Golden Handcuffs because you have the value of a regular paycheck but it comes at the price of your freedom.   It can be a difficult dilemma to be in when you need to have a source of steady income but you also want to strike out on your own and pursue your dream of owning your own business.

Before you take that plunge, you need to carefully weigh your options and, just as importantly, you need to be able to do a personal assessment to see if you have the right temperament for self-employment.   Being your own boss is not for everyone.    You must, by nature, be a risk taker.    I believe you cannot survive in business if you cannot accept and tolerate a certain amount of risk and uncertainty.

You, also, must be able to make decisions quickly.   I feel that sometimes even a bad decision can be better than no decision.   Being indecisive can be disastrous for your business.

Finally, you need to be a bit of a perfectionist and have a very low tolerance for mistakes, particularly, if it is as the result of poor preparation or attention to details.

I, early on in my career, knew that I would not and could not work for anyone but myself.   I was prepared to take the risks in return for my freedom.   I started out each year not knowing how much I would make or even if I would make enough to support myself and my family.   All I could rely on was my belief in my abilities and the confidence to feel that I would find a way to succeed.    It was not always easy, but I always found it to be rewarding even if I had a lean year once in awhile. 

If you want to be your own boss and start a business, my best advice is to do your homework, have a realistic business plan, be prepared to take some calculated risks, and do not get attached to those Golden Handcuffs.



My father, for most of his working life, was self-employed and operated a scrap metal recycling business.   My father was raised by immigrant parents during the Great Depression and never received much in the way of a formal education having gone only as far as the eighth grade; however, he has plenty of common sense and street smarts.  

As a small business owner, he was tenacious, worked hard and always found a way to make a living and provide for his family.   As a child, I could usually tell how his business was going by what my mother made for dinner.   If we were having a lot of pasta things were not going so well and if steak showed up on the menu things were looking up.  

I can’t tell you when I first decided that I would rather work for myself then for someone else.   However, growing up, I certainly was aware of the fact that my father was self-employed and I am sure this made an impression on me.   In fact, I worked with my father several summers during high school and saw firsthand what it was like being your own boss.

After my first year of law school, I took some time off and worked at a large national company in Boston and saw what life was like as an employee.   After a year of this, I realized it was not for me and I decided to finish my law school studies.

While I was back in law school, my brother and I started our own recycling business which we operated for about two years.  We developed agreements with manufacturing and utility companies to recycle the lead from large industrial batteries and dealt with other items that no one, not even my father, wanted to handle.  We made a very good profit on this business and it helped me further understand that working for myself could produce rewarding results.

By the time I started practicing law and after working for a large firm for several years, to gain some useful experience, I knew that I would spend the rest of my career working for myself.    Early in my career, I even turned down a position as an attorney with the state government.

I was, by that time, fully prepared to give up the security of receiving a steady paycheck and benefits as someone’s employee for the chance to be my own boss, take my own risks, and earn a potentially unlimited amount of income.

I enjoy the freedom of being my own boss and running my business the way that I see fit.   In addition to the freedom, I like the idea that whether I succeed or fail, it is all based on my efforts and not from the actions or failures of someone else.                

I feel that I am in control of my own destiny.