"It's only half past twelve, but I don't care.  It's five o' clock somewhere."

- Alan Jackson and Jimmy Buffett

Five o'clock is important to many people. It is the time that they leave their jobs and stop thinking about work.

Five o'clock has never been a big deal for me. I've been self-employed for 25 years, and my work does not conform to a time clock.

My father was a gambler and never lived a nine to five life. Thus, I never grew up wanting one.

Several of my clients are trial attorneys. Along with the bond of working with injured people, we have another common tie: we don't know when we are going to be paid.

The book and movie A Civil Action is a good example of how an attorney can go broke working on an important case.

Many professionals, like real estate agents and others in the sales industry, have the same kind of up-and-down incomes.

Few people are suited to be their own boss. Most people want a regular work routine. Their lives are based on a 40-hour work week and a steady paycheck.  

When people tell me they want to start their own business, I ask them if they can really live without a regular income. I tell them to talk to their families and get their honest answers. I ask them if they could stand to go weeks or months without money coming in and how they would deal with it.  

They need to understand they are trading their steady paycheck for an "unsteady paycheck."

Many people want their own businesses for the wrong reasons. Like the character in the Jackson song, people decide that they don't like their jobs and that it would be fun to be self-employed.

They don't realize that self-employment means that it is never five o'clock anywhere.

I've told many professionals that they should not go into business for themselves. They may be good workers with good ideas, but they could not handle the stress from not having a guaranteed income. 

Never being off work can be hard on families. I had a friend try to be an independent insurance agent. He worked a lot of hours and his wife put their children on the phone and had them say how much they missed him.

He went back to a steady paycheck at a big insurance company. He has less independence but he is still married. 

Some people, like me, became self-employed because no large organization would hire them. Once I started my financial business, I realized that I needed the independence of being self-employed more than I needed a steady paycheck.

I had a brief career at a company that decided to impose a dress code. I immediately started coming to work wearing blue jeans, a tee shirt, and a Cincinnati Reds baseball cap.

I killed the dress code and any hope of my advancement at the same time. I went back to working on my own.  

Education and upbringing are important in deciding whether a person can make it as an entrepreneur. I was with Barbourville, Ky. attorney Sam Davies when a woman told him that she was sending her son to military school. "He will learn how to follow the rules," she said. Sam replied, "He would be better off if he found a school where they taught him how not to follow the rules."

Sam, who has never had a partner, is one of the best attorneys in the United States. Many trial lawyers practice by themselves or with a few associates. Most have the same anti-authority attitude that I have. 

The attitude that makes them unafraid to take on billion-dollar businesses makes it impossible for them to fit into a big corporation. 

They produce an "unsteady paycheck," and they never know when five o'clock rolls around.

Before a person decides on self employment, they need to figure out how important five o' clock is in their lives.

Story Behind the Song

It's Five O'clock Somewhere

This song was a monster hit that seems to hit a nerve. Also, it brought Jimmy Buffett back on the popular charts about 25 years after his last visit on the top 20. 

 
Here is a link to the video: 

http://www.youtube.com/watch?v=ib8nH4kHjxk 

Don McNay is Chairman of the Board for McNay Settlement Group in Richmond, Ky.  He is the author of the soon to be released book: Son of a Son of a Gambler: Winners, Losers and What to Do When You Win the Lottery. You can write to him at This e-mail address is being protected from spam bots, you need JavaScript enabled to view it or read other things he has written at www.donmcnay.com. His award winning column is syndicated to over 200 publications.