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If I Were a Rich Man

David Gartland

FIDDLER ON THE ROOF is the timeless tale of a poor Jewish dairy farmer in Russia during the early 20th century. What makes the musical timeless? It tells the story of a worker, husband, father and religious believer who’s trying to succeed in all these facets of his life.

One of the show’s most famous songs is, “If I Were a Rich Man.” As the title implies, the farmer dreams of a life of wealth and how wonderful that would be. I suspect that most, if not all, HumbleDollar readers are either wealthy or would like to be. And, of course, we could all be richer still. That’s the beauty and the curse of money. There’s always the possibility of having more.

To set the record straight, I once again didn’t win the billion-dollar-plus Powerball jackpot. Every time the jackpot reaches the stratosphere, I buy a ticket and then drift off into dreamland, wondering what it would be like if I were a rich man.

I’ve had a taste of the Rich and Famous lifestyle. My wife used to work for an Irish international packaging company. One of the company’s assets was a condo at Trump Tower in New York City. My wife was friendly with the housekeeper, who would tell my wife when the condo wasn’t being used. One night, I got to sleep over there. Steven Spielberg lived in the condo above.

When the founder of the packaging company died, his sons took over the company’s management. One of the sons, who was the CEO, kept suits at the condo, so he wouldn’t need to pack a suitcase when he flew from Dublin to New York. Occasionally, he would get rid of suits that he no longer wanted. My wife brought one of these suits home and it was a perfect fit. It was a high-quality wool suit, and I wore it for years. For fun, when I looked in the mirror, I’d say, “I guess this is what a millionaire looks like.”

My wife would tell me about the sons and how they lived the millionaire lifestyle. A middle-class family might have a house, one or two cars, a job, two kids and a bank account. The millionaire lifestyle amplifies these elements—in a big way.

It isn’t just the full-time housekeeper. Multi-millionaires don’t own just one house; they own multiple homes. They don’t hope their kids get college scholarships; they pay cash for any college their kids want to go to. And on and on it goes.

This mental shift seems simple, but it must take a lot of work. Money can’t just trickle out of your pocket. It’s really got to flow, or you’ll have a log jam. You have to write six-figure checks, and be happy doing it.

For inexperienced wealthy people, like those who suddenly win the Powerball, there’s a risk they’ll blow it. They’ll likely be overwhelmed by their newfound wealth and they probably don’t know how to handle it. They need financial advisors, lawyers and accountants who can provide the guidance they so desperately need.

The wealthy do the same things that all of us do, they just do them bigger. They give to charities, like we all do, but they have wings on hospitals and buildings at their alma mater with their names attached. They find ways to spend big money and do it gracefully.

Whenever I buy my $2 ticket and indulge in wishful thinking, I try to figure out how I’d spend my winnings, but I can’t. I’m locked into the poor man’s thought process that’s been there my entire life.

Every time, I ask myself the same question: Would I be happier if I owned _____? Whatever expensive toy I imagine, I always talk myself out of buying it because I don’t need it. If I owned a yacht, I don’t see how I’d be happier. In fact, I had to look up how to spell yacht. I can spell boat, which is as far as my mindset allows me to go. But that’s my point: Big money is not in my wheelhouse.

If you’re a believer in the law of attraction, where visualizing something can somehow bring it into being, you’ll understand why I haven’t won the big one. I suffer from poor man’s thinking. I think too small and, indeed, I’m happy thinking small. To me, more stuff means more problems.

No doubt about it, being poor sucks and being rich is better. But if you win the Powerball, you’d better be prepared to handle the new lifestyle. If not, others will likely live that lifestyle at your expense. Don’t believe me? Just look up MC Hammer’s story.

David Gartland was born and raised on Long Island, New York, and has lived in central New Jersey since 1987. He earned a bachelor’s degree in math from the State University of New York at Cortland and holds various professional insurance designations. Dave’s property and casualty insurance career with different companies lasted 42 years. He’s been married 36 years, and has a son with special needs. Dave has identified three areas of interest that he focuses on to enjoy retirement: exploring, learning and accomplishing. Pursuing any one of these leads to contentment. Check out Dave’s earlier articles.

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