Better to Have Been Rich and Lost It, or Never Been Rich at All?

mod (Andy) note: "Blast from the past - Best of Eddie" - This one is originally from November 2010. If there's an old post from Eddie you'd like to see up again shoot me a message.

When I was in my teens and early 20's, all I could think about was being rich. I didn't care what I had to do to make the money, I just knew that I wanted to be rich. Not just wealthy, either. I wanted the private jets, the boats, the mansions, the proverbial "fuck you" money. What I didn't spend any time thinking about was what would happen if I made that kind of money and then lost it.

I was reminded of this when I read the story of the Martin family of Paso Robles, California. This is the story of a husband and wife with three kids who made $10 million after taxes from the sale of his father's company in 1998. Today all the money is gone, along with their sprawling estate, his Aston Martin, and her horses - one of which cost $173,000. He went from jet-setting and dinners at the "21" club to teaching at a community college in Kansas in just over 10 years. And it got me thinking about which was worse: to be rich and lose everything, or to have never been rich and not know what you're missing?

I never ended up making "fuck you" money, but I did pretty well for myself early on. For a lower middle-class mailman's kid, I threw up some pretty respectable numbers and quickly got used to the good life. When money is an issue for you your whole life and then suddenly it isn't really, you can either react responsibly and act like you've been in the end zone before, or you can act like a jackass and get flagged for excessive celebration in the Super Bowl of life.

You can probably guess which route I took. I'm still pulling the occasional yellow flag out of my ass from those days.

The money only amplified an already pretty ugly aspect of my personality and, through a series of self-destructive decisions and actions, I lost everything and basically had to spend a year of my life on the run in Mexico and the Far East. The details are unimportant at this point, but what is important is how brutal it was to have had a little dough and then lost it.

The fortunate thing for me was that this happened early in life, and I was able to recover from it. Not only was I able to bounce back, I made even more money the next time. And then I lost that, too. As long as you keep learning from your mistakes, making the money back gets easier each time.

But I'm forced to wonder what life would have been like if I had taken my dad's advice and become a vehicle maintenance officer for the Post Office. Would pulling down $40,000 a year (or whatever they make, I have no idea), loading up the station wagon for a vacation to Disneyland once a year, and living in a 1,300 sq ft 3-bedroom place in the burbs have been preferable to the wealth roller coaster I've ridden for most of my adult life?

I think not. We only go through life once, and I think experiences are the only real currency in this existence. Trying to keep things stable and steady kinda defeats the purpose in my view. Being rich teaches you that money can't buy everything (and that's a lesson you have to learn for yourself to ever really believe it) and being poor teaches you to be resourceful in ways only those who've been there can appreciate. There is great value in both experiences, but I'll grant you that being rich is better than being poor.

What do you think? What do you suppose the Martins think? It has to be especially difficult for their kids to have had everything and then lost it and have to move to where the "poor" people live.

Is it better to have been rich and lost it, or to have never been rich at all?

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