09/10/2009 05:12 am ET Updated May 25, 2011

Are You Cut Out To Be Self Employed?

"It's only half past 12, 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 most of my adult life, 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.

Many of my clients are self-employed 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 attorneys advance thousands of dollars on cases expenses and never know if they can recoup those expenses.

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 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 couldn't 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 started calling his office in the evenings. She 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 became self-employed because no large organization would hire them. I did not plan to be self-employed, but I could not find a job out of graduate school other than cleaning up at the Kentucky Horse Park. 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 have an anti-authority edge that makes it difficult for me to handle corporate rules. I have tried to merge my business into big organizations a couple of times, and it has never worked.

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.

Don McNay, CLU, ChFC, MSFS, CSSC is one of the world's leading authorities in helping injured people and lottery winners deal with complex financial issues.

McNay is also an award winning syndicated financial columnist.

McNay founded McNay Settlement Group, a structured settlement and financial consulting firm, in 1983. The company's primary office is in Richmond, Kentucky.

McNay has Master's Degrees from Vanderbilt and the American College and is in the Eastern Kentucky University Hall of Distinguished Alumni.

McNay has written two books. Most recent is Son of a Son of a Gambler: Winners, Losers and What to Do When You When The Lottery

You can write to Don at or read his column at
You can reach him on Facebook at and on Twitter at

McNay is a lifetime member of the Million Dollar Round Table and has four professional designations in the financial services field.