When Do You Stop Taking Financial Risks?

“I can’t go on the same old way
Can’t keep up the same old game
Why can’t you just get it through your head?
It’s over, it’s over now” 
-Boz Scaggs

I know a wealthy, self-made man who made most of his money before age 45.

I looked at his financial information and told him, “You are not going to stop working until you drop over dead. If you wanted to retire, you could have done that a long time ago. You like what you do and will never stop.”

My statement shook his inner psyche, and then he realized I was right. He never truly plans to quit.

He realized I operate in the same fashion. The idea of sitting in a rocking chair and playing shuffle board is not in my game plan.

Someone once asked when I would retire. I responded death.

My work brings me great joy. I can’t imagine ever giving it up.

The great Kentuckian Al Smith wrote his first book at age 84, and at age 85, just finished his second book, “Kentucky Cured,” which will be released in November.

Al always has something to do and some place to go.

Al is an interesting role model in that he had a full-time job for twenty years. Years ago, he sold his chain of newspapers and devoted the rest of his life to helping others.

I’m not privy to Al’s financial information, but suspect he and his wife set up their finances with a long-term view in mind.

Which is what I would like some former professional athletes to do.

Sports Illustrated did a fascinating study in 2009 titled “How (and Why) Athletes Go Broke.” The statistics are stunning. By the time they have been retired for two years, 78 percent of former NFL football players have gone bankrupt or are under financial stress because of joblessness or divorce. Within five years of retirement, an estimated 60 percent of former NBA basketball players are broke.

These are people who made millions. What happened?

I see a lot of them blow money on large entourages and wild spending, the same way many lottery winners do. But I see a lot more get burned by getting involved in businesses far away from their area of expertise.

According to the USA Today, my childhood hero, Oscar Robertson, has a plethora of tax and financial problems related to a chemical company he owns.

Robertson is not only a basketball legend; he has been a devoted community advocate who has lived his life in an exemplary fashion.

At age 73, it’s going to be tough for the Big O to make big money again.

People often ask me, “Why don’t some of these professional athletes put their money in the bank or a lifetime annuity? They don’t need to do anything risky or stupid.”

A good question.

I suspect that the same type of confidence and courage that allows someone to become a professional athlete works against them in the business world.

They never know when to go to the sidelines.

It’s not that hard to be financially secure. You spend less than you make, you save the rest and don’t do anything stupid. You assume you are going to live to an extremely old age and make sure you have money that lasts as long as you do.

It’s not hard, but it’s tedious. And it’s not the least bit glamorous.

I knew of a woman who was always trying to meet a guy driving a new Mercedes.

She should have been looking for someone who drives a 10-year-old Toyota. The Toyota driver is more likely to have real wealth in the long run.

The focus on long-term savings is the primary difference between my friend who has real wealth and big stars who have spent real wealth.

My friend accumulated his wealth quietly and protects his money carefully. I can testify that he is intensely frugal and has no inner need to show off his wealth. His money is a byproduct of his focus on putting out a quality product.

He also knows his business. Inside and out. He knows as much about his industry as Oscar Robertson knows
about basketball.

He goes to work every day because he enjoys operating at the peak of his potential. Just like Oscar Robertson did when he played basketball.

Oscar got out of basketball near the top of his game. After the Cincinnati Royals made the silly mistake of trading him in 1970, he led the Milwaukee Bucks to an NBA championship before he stepped down in 1974.

I hope he works out his financial problems and leaves the business world on top as well.

He is a classy guy who needs to ask himself an important question: At what point do you stop taking
financial risks?

Don McNay, who lives in Richmond, Ky., is an award-winning financial columnist for Huffington Post Contributor. You can learn more about him at www.donmcnay.com.