For the past few columns, we’ve been exploring some of the rich and famous and their money stories.

Some vignettes have been celebratory, and others have reflected tragic financial debacles. From mismanagement of finances to lack of planning for the future, these latter scenarios left opportunities behind.

None of these celebrities planned to fail. How then, with the resources they had at their disposal, did this occur? Why did they not seek the help of experts and do the right thing?

Fear and denial can actually keep all of us – not just celebrities – from good financial planning.

“I will never die.”

Although most of us rationally know that this life is temporal, many people operate as though they are untouched by mortality. The fact is, nobody likes to think that one day their life will end. And when faced with making plans for an estate, no matter how large or small, it is a sobering moment. Many will avoid thinking about such things, for it brings about painful emotions and the anticipation of difficult conversations.

Pablo Picasso did not leave a will. The famous artist did, instead, leave a trail of heirs consisting of wives, mistresses, legitimate and illegitimate children. They were left behind to figure things out in a messy and long court saga.

Moving through the reality of one’s mortality and feeling better about it is ironically solved by talking about your hesitancy with an estate planning attorney. This professional is well-versed in handling difficult conversations and in helping clients deal with challenging feelings and situations.

By the time I completed my estate plans with my own attorney, I felt relieved and at peace, which has probably added years back to my life.

“I’m feeling lucky.”

Perhaps Kim Basinger was feeling lucky when she spent $20 million in 1989 for the town of Braselton, Georgia.

Intending to make it a tourist attraction, she had to declare bankruptcy four years later and sell the property. This might have been a good investment in theory. I can’t vouch for how well Basinger did her market research, and I don’t know if she had a good business plan.

However, having to declare bankruptcy a scant handful of years later makes me question all this, as well as wondering what kind of financial advisement she received as she wrote that huge check.

You might be feeling lucky, too. Are there ways that you are spending your money that aren’t working well for you? Money always needs a place to go. Talk with a financial adviser to put yours to work for you.

“I live above the law.”

Willie Nelson lived above the law for a long time. A lovable and talented musician, he amassed great wealth until 1990. Then the IRS caught up to him.

The feds claimed Nelson owed them $32 million in taxes and seized properties belonging to him in six states, including his master recording tapes, his platinum records and even personal articles of clothing. Even after taking possession of all this, the IRS calculated Nelson still owed them about $16.7 million.

Three years later, they settled for $9 million. Willie claimed that he had found himself in this pickle because of mismanaged funds and poor advice from accountants. If some of you reading this are clucking your tongues, there are others of you who may be squirming a bit.

It can be tempting to think about reporting less on your tax returns, or handing someone cash for payment to avoid taxes. After all, you work hard for your money – right? If this is you, think again.