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I’ve always been intrigued by financial advisors. It was one of the few careers where people are always asking each other, “How much money do you make?” Of course, they’re not that obvious. They say things like, “What did you gross last year?” or “What are your assets under management?”

Once they have this coveted information, they quickly do the math in their head … all the while acting like they’re interested in what you’re saying. Within seconds, most can figure out, within about 50 cents, what your monthly take-home pay is.

With this information in hand, they determine whether or not you’re full of BS. Generally, if your income is less than theirs, they feel superior and everything you say is mortally flawed. If your income is higher (and only then) you get their respect and they assume you know what you’re talking about. At that point, your conversation becomes much more interesting.

This environment can lead to envy and jealousy. Think about the last big broker conference you went to. You knew who all the big hitters were, didn’t you? Didn’t you feel a tinge of jealousy about how much money they were making? A little? If only you had the same breaks they did (is usually what I thought).

A million years ago, when I was wholesaling I met an advisor on his company’s “Grand Awards Trip.” He was one of the top reps in his firm. He made a ton of money, had his pretty little wife and 2.3 perfect children. I’m sure his dog never pooped in the house either. I used to think, “Wow, what a life this guy has. I wish …”

Five years later, I had moved on and lost touch with this advisor. When I got back in touch with some of my old friends at the rep’s firm, I learned he was no longer there. Apparently he had sold a ton of private placements that went into the toilet. He started boozing and his wife left him. I’m not sure, but I think he’s managing a Hooters restaurant now. The money’s not as good but he gets all the chicken wings he can eat.

More recently, I met a guy who became a good friend. He was a trader on Wall Street. He worked for a big hedge fund. I always was in awe of him. He had a great family. He was witty and charming. And of course, he had great toys. We’d drive in his Mercedes to the marina to take his boat out fishing. Thankfully he paid for the gas so I wouldn’t have to raid my 401(k).

I knew my buddy for about eight or nine years. By this time, I had settled into the realization that others around me were just more successful and more talented. This was to be my lot in life. The perfect little family unit, unlimited funds and a dog with no bowels were just not in the cards for me.

Imagine my surprise when my phone rang early one morning and I learned that in the middle of the night, the FBI had surrounded my friend’s house and he was in jail. Allegedly, he was involved in some big insider-trading scheme. Lawyers drained what money he had left. His house is up for sale and his wife went back to work. He now will be spending the next four or five years banging out license plates, between sets of tennis, at a minimum-security prison camp.

As you can probably tell by now, I just can’t get seem to get this envy/jealousy thing right. I end up being jealous of the wrong people. Maybe a better strategy is to simply appreciate what I have and the work it took to get it. From now on, that’s what I’ll do. I’ve got a fun interesting career and three great teenage boys who can’t seem to put anything away or pick up after themselves.

I’m going to start appreciating all that, right after I clean up my dog’s latest mess.